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Attacking WinZip AES Encryption

bden writes "As another tidbit from Bruce Schneier's Crypto-Gram, remember back in January when WinZip was Slashdotted for moving forward with its new AES-based encryption technology? Everything sounded good since we all knew that AES is secure, right? Well, a cryptographer took a look at how WinZip uses AES and found lots of problems. Regardless of how many people actually plan to use WinZip encryption, the lesson, according to Schneier, is that "cryptography is hard, and simply using AES in a product does not magically make it secure." So how can we distinguish between an application that simply uses the right buzzwords, like AES, from an application that is actually secure?"

227 comments

  1. is this a testament to today's computing power? by sjwaste · · Score: 2, Insightful

    Like the subject says, could carelessness in encryption have been a non factor even a couple years ago? Does the raw processing power on the average desktop make it that much easier to exploit a mistake or break weak encryption? In any case, I hope Winzip realizes "security" and "encryption" are more than just buzzwords.

    1. Re:is this a testament to today's computing power? by TedCheshireAcad · · Score: 5, Insightful

      I took a class in cryptography last semester. The professor offered the best words of advice I ever heard in the subject: "Don't try to create new algorithms. We know how to do that already. What we have is secure. What you need to work on is the implementation. Just because something uses encryption, it is by no means secure."

      He then proceeded to explain how easily NTLM can be defeated in a brute force attack.

    2. Re:is this a testament to today's computing power? by Cthefuture · · Score: 4, Insightful

      I didn't read the whole paper but the first attack was dealing with the meta-data.

      What I can't believe is that they would still leave so much stuff unencrypted. A very poor design decision.

      I mean, how freaking hard is it to put a flag at the start of the archive saying it is encrypted and then just raw encrypt the rest of the data. That design seems obvious and would be as secure as AES can be (eg. just create a normal zip, encrypt it, add flag/tag at start).

      --
      The ratio of people to cake is too big
    3. Re:is this a testament to today's computing power? by Anonymous Coward · · Score: 2, Funny

      He then proceeded to explain how easily NTLM can be defeated in a brute force attack.

      Suddenly the students started listening and taking notes!!! :)

    4. Re:is this a testament to today's computing power? by rolux · · Score: 3, Interesting

      Actually it's not a poor design decision but a stupid feature. They want the file hierarchy within the archive to be browseable without decryption (TFA also briefly mentions that). Zillions of winzip users seem to value that feature higher than protection against such middleman attacks. And the developers, even though they must have a clue, seem to agree.

      Similarly, TFA mentions a piece of documentation advising to encrypt all files in an archive in order to avoid warning dialogues about some unencrypted (and thus potentially modified) files. Seems to be viewed as a user experience concern, not a security concern. Quite a shame...

      --
      My next comment will be ready soon, but moderators can beat the rush and mod it up early.
    5. Re:is this a testament to today's computing power? by badmammajamma · · Score: 2, Insightful

      lol...there are LOTS of things vulnerable to brute force attacks. Security is a joke because most companies simply say they support this and that so they can put a checkmark in their feature list. It's not that they really care to make anything secure. Even in rare cases where an implementation is good, it's even more rare that a good password is used (which is essential regardless of how fancy your encryption) because people can't remember long passwords and software rarely requires users to pick secure passwords.

      --
      Any man who afflicts the human race with ideas must be prepared to see them misunderstood. -- H. L. Mencken
    6. Re:is this a testament to today's computing power? by Q+Who · · Score: 0, Offtopic

      I took a class in cryptography last semester. The professor offered the best words of advice I ever heard in the subject: "Don't try to create new algorithms. We know how to do that already. What we have is secure. What you need to work on is the implementation. Just because something uses encryption, it is by no means secure."

      It wasn't a class in cryptography then. Topics in applied cryptography? Some mini-project?

    7. Re:is this a testament to today's computing power? by Anonymous Coward · · Score: 0

      Score:-1, Conservative

      Score: -2, Self-Righteous

    8. Re:is this a testament to today's computing power? by andalay · · Score: 1

      No, its the hidden fact that the NSA asks companies to introduce weaknesses into cryptographic products that may be exported outside the US.

    9. Re:is this a testament to today's computing power? by Anonymous Coward · · Score: 1

      It wasn't a class in cryptography then. Topics in applied cryptography? Some mini-project?


      Honestly, eat shit.
      What a fucking asshole you are.

      How can you conclude the overall subject matter and topic of the class based on one statement that the professor made throughout the term.

    10. Re:is this a testament to today's computing power? by Fallen_Knight · · Score: 1

      its nice winrar has the option to encrypt the entrie archive, in fact i do belive that th eonly way to tell if a file is a encrypted winrar archive is to look for RAR in the first 3 bytes. remove that and you wouldn't know what the file is

    11. Re:is this a testament to today's computing power? by Stormie · · Score: 1

      They want the file hierarchy within the archive to be browseable without decryption (TFA also briefly mentions that). Zillions of winzip users seem to value that feature higher than protection against such middleman attacks.

      Yeah, but zillions of other Winzip users HATE that feature, because it means they have to rename all their pr0n to have less.. err.. explicit filenames, before they can zip it up in a password-protected zip and feel secure.

    12. Re:is this a testament to today's computing power? by chgros · · Score: 1

      Like the subject says, could carelessness in encryption have been a non factor even a couple years ago? Does the raw processing power on the average desktop make it that much easier to exploit a mistake or break weak encryption?
      From my crypto teacher: "you can break css on a wristwatch". The processing power of today's machine is not always a factor.

    13. Re:is this a testament to today's computing power? by dasmegabyte · · Score: 1

      But the nice thing is, if somebody sends you an archive, you can tell what files it purports to have before decrypting them. Useful for when you get an encrypted zip file and, lo and behold, it's full of virus scripts.

      If you want to encrypt your porn, you really shouldn't be using ZIP for it, man. Encrypted zips are to secure and encapsulate data, not obfuscate it. For that...may I suggest Jetico's BestCrypt suite (if'n you're stuck with windows), which is efficient, fast, and lets you use any level or method of encryption you like, customize random generation, key length and strength, etc. You basically make an encrypter container and mount it like a filesystem...also useful for encrypting your Freenet temp files and object store, if you're into that.

      --
      Hey freaks: now you're ju
    14. Re:is this a testament to today's computing power? by kabloom · · Score: 1

      Even if he's not teaching them to create new algorithms, he's teaching them the existing ones, which certainly falls under the course title of cryptography.

    15. Re:is this a testament to today's computing power? by Q+Who · · Score: 1

      Community college?

    16. Re:is this a testament to today's computing power? by Anonymous Coward · · Score: 0

      There's nothing wrong with community college. If the non-community world is turning out two bit self important asswipes like yourself, the world would be better without them. You're an arrogant son of a bitch that should have never walked the earth.

    17. Re:is this a testament to today's computing power? by JayAdams · · Score: 0

      Wow, with more than 2 zillion users out there, I'd better buy some WinZip stock!!

    18. Re:is this a testament to today's computing power? by Q+Who · · Score: 1

      In other words, I was right on both issues.

      P.S. "Non-community world" - heh. I'm not even American, clown.

  2. The answer is simple... by gid13 · · Score: 1, Interesting

    More buzzwords!

    Seriously, however, perhaps the best ways to have a secure product are to examine the implementation yourself, or try to attack it yourself, or wait for those who know more than you to do the same, and read about it.

    1. Re:The answer is simple... by whiteranger99x · · Score: 1

      Yeah, but as a company trying to sell a product that lists that as a feature, who's in their right mind going to want to prove that their implementation in their own product is a piece of shit?

      Although I must ask that if you rely solely on encrypting files in a WinZIP archive, then we already have problems from the get go!

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    2. Re: The answer is simple... by Black+Parrot · · Score: 1


      > More buzzwords!

      Since there are more buzzwords than there are letters in the alphabet, strings of buzzwords would probably make good passphrases.

      Now, if only we had buzzword keyboards...

      --
      Sheesh, evil *and* a jerk. -- Jade
    3. Re: The answer is simple... by whiteranger99x · · Score: 1

      Yeah, but them you'll have a bunch of people that will use "XP" or a single key as their passphrase. :P

      Although some choice keys might be:
      XP
      W00T
      SUX
      ROX
      PERL
      PYTHON
      M$/MS/Micro $oft/MicroShaft (any and all iterations)
      Obfustication
      DMCA
      Free Mitnick
      FCC Violation
      WEP
      WAP
      Wardrobe Malfunction
      PWN3D!!

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    4. Re:The answer is simple... by JPriest · · Score: 1

      Well if the implementation didn't suck and long hashes are used it's actually a pretty good method to encrypt files in "real-world" use.

      --
      Saying Java is nice because it works on all OS's is like saying that anal sex is nice because it works on all genders.
    5. Re: The answer is simple... by Mad+Marlin · · Score: 1

      What, no Joshua?

    6. Re:The answer is simple... by bstone · · Score: 2, Funny

      wait for those who know more than you to do the same, and read about it

      The easy way to avoid having someone else break your encryption is to put some copyrite data in the files, then sue them into oblivion under the DMCA if anyone tries it:)

  3. Simple by Anonymous Coward · · Score: 5, Insightful

    So how can we distinguish between an application that simply uses the right buzzwords, like AES, from an application that is actually secure?"

    By only using peer reviewed open source software for starters.

    FP?

    1. Re:Simple by Anonymous Coward · · Score: 5, Funny

      Yes, like sendmail.

    2. Re:Simple by enditallnow · · Score: 5, Insightful
      Its questionable whether this would help commercial applications. Not every company offering secure programs wants their source code floating about the internet (Insert Microsoft Joke Here).

      I agree that the best way to ensure that an application is secure is for it to be reviewed by someone who knows their shit. Quite simply its the only way to be sure at this point in time. Perhaps an authoritive body should be formed comprising of cryptographers that grants their seal of approval on it. Then again, doesn't the US government have to give its authorisation for cryptographic software to be exported? I recall that DES had to go through such motions, and if i'm not mistaken PGP can't be shipped outside of the US because its considered military grade cryptography? If im wrong please correct me, its been a while since I read over this topic and my memory is a bit hazy.

      BTW, open source does not necessarily imply increased security. I'd rather have the word that a piece of software is secure from a professional like Bruce Schneier rather than an Open Source zealot who skimmed over a copy "Applied Cryptography" in their local Borders.

      -- Enditallnow

    3. Re:Simple by wfberg · · Score: 4, Informative

      So how can we distinguish between an application that simply uses the right buzzwords, like AES, from an application that is actually secure?"

      By only using peer reviewed open source software for starters.


      Also note how the "UNIX" tradition of chaining smaller, single-purpose applications together would have also prevented the problems described in this paper.
      If you first create an archive (tar.bz or even ZIP), and then run it through gpg, the metadata is encrypted by default, and these problems would not have arisen.
      Furthermore, there's no need to check every archiver under the sun for subtle encryption snafus, since the encryption is done by a specialized application. Wheter you GPG a .rar or a .zip, you only need to look at GPG to find bugs. And if and when you do, fix GPG, or use something else.

      I wonder why people use a .ZIP plugin in outlook to encrypt mail, even though outlook has encryption (though admittedly, using cumbersomely acquired SSL certificates) built right in..

      Also note that in the EU (now 25 countries!) public key cryptography such as GPG and SSL is all but mandated for electronic signatures that will stand up in court; better to use public key crypto than to rely on a shared key if you need to rely on file's or email's authenticity/non-repudiation.

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    4. Re:Simple by John+Starks · · Score: 2, Insightful

      That might do the trick (though it usually doesn't, as another poster alluded to re: sendmail). But it is sufficient, and perhaps preferred, to simply open specifications for others to implement, as WinZip did.

      I say preferred because with an open specification, peer review is more likely since competitors and open source users alike will try to implement the specification, thus enforcing the "many eyes" ideal. If there was an Open Source zip program that everyone used, there would probably be less competition, and thus chances increase that everyone would use its encryption features blindly. Couple this with the fact that file formats for Open Source products, when nonstandard, are usually only specified as code and not in a separate, analyzable document, and the "many eyes" phenomenon becomes much more unlikely.

      So I agree that SOMETHING needs to be open, but I'd contend it's more important that the specification be open and released as a separate document than just have the source be open alone.

    5. Re:Simple by Krunch · · Score: 3, Informative

      GPG (and PGP) already compress the encrypted data. It seems PGP only use the .zip format but GPG also support bzip2 and gzip. Look at the -z and --compress-algo options of GPG.

      --
      No GNU has been Hurd during the making of this comment.
    6. Re:Simple by elfkicker · · Score: 1

      Using FIPS compliant software and devices would also be a good start.

    7. Re:Simple by wfberg · · Score: 2, Informative

      GPG (and PGP) already compress the encrypted data. It seems PGP only use the .zip format but GPG also support bzip2 and gzip. Look at the -z and --compress-algo options of GPG.

      PGP/GPG uses compression for security purposes (remove as much entropy as possible) but IIRC it doesn't archive; i.e. include multiple files (and a directory structure) in one file.

      This capability is precisely what bit WinZip in the ass (WinZip lives for archiving) because they left the meta-data that lists filenames etc. unencrypted.

      Archiving multiple files before encrypting them is also a good idea, since you'd be sending out as much as possible in one go - if you encrypt each file separately you're again leaving meta-data around the place (if only the fact that you sent n emails, 1 of size 10K, the other.. etc.).

      Encrypted military communications lines are said to be transmitting constantly, even when not being used to send messages (sending garbage in stead) to prevent any eaves dropper from detecting sudden spikes in communications. Kind of like installing one of those suspensions that rocks your car about to prevent people from guessing when the van's a-rockin', don't come a knockin'..

      Note that WinZip could just as well use/invoke GPG "under the hood" without users even knowing about it.

      --
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    8. Re:Simple by j0hnn135 · · Score: 1
      I agree about the review process. However, the more people that review the technology, the higher the probability that security vulnerabilities are addressed. Of course open source does have the advantage of code level review by anyone who is interested, where "commercial" software is only reviewed by those with an NDA. Usually that means the company is paying contractors.

      I love Bruce as much as the next security guy, but no one is perfect. So, I think multiple layers are review are appropriate under any good system. Hopefully driven more around teaching developers how to write better code rather than just catching flaws.

      I heard in numerous presentation that export laws have been significantly relaxed. Here is RSA's perspective on the new export landscape. I'm glad they finally made this move, since trying to control public crypto is like trying to catch rain in you hands.

      -J

    9. Re:Simple by Krunch · · Score: 1
      PGP/GPG uses compression for security purposes (remove as much entropy as possible) but IIRC it doesn't archive; i.e. include multiple files (and a directory structure) in one file.
      That's what tar is for.
      tar -c $FILES | gpg -s -e -r $RECIPIENT > compressed-and-encrypted-files.asc
      Send that through netcat and you got a somewhat secure way of sending files to anybody who can configure his firewall. Who use Winzip anyway ?
      --
      No GNU has been Hurd during the making of this comment.
    10. Re:Simple by c · · Score: 1

      Then again, doesn't the US government have to give its authorisation for cryptographic software to be exported? I recall that DES had to go through such motions, and if i'm not mistaken PGP can't be shipped outside of the US because its considered military grade cryptography?

      Exactly. If you want to find out if your crypto implementation is secure, ask the US government. If they say yes, you've got bugs.

      Mind you, I'm not sure why anyone would need to ask permission to export a public standard like AES. I'm pretty sure there aren't any secrets happening there.

      c.

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    11. Re:Simple by Anonymous Coward · · Score: 2, Interesting

      Not every company offering secure programs wants their source code floating about the internet...

      And I should care exactly why? If companies cannot deliver secure software without releasing source code, then they had darn well better release their source. Their preference is irrelevant to that decision.

      (Note, pedants, that I said "if" security requires source code release.)

      I'd rather have the word that a piece of software is secure from a professional like Bruce Schneier rather than an Open Source zealot who skimmed over a copy "Applied Cryptography" in their local Borders.

      Well, I'd rather have the authors of OpenSSL, OpenSSH, and FreeSWAN review my code than some overpaid consultant who skimmed over a copy of "Applied Cryptography" in their consultancy library.

      Of course, it's a bit more likely that I'll get the OpenSSL/OpenSSH/FreeSWAN authors to review my code than it is that you'll get Bruce Schneier to review yours.

    12. Re:Simple by Some+Dumbass... · · Score: 1

      Yes, like sendmail.

      Uh, I think that when talking about "peer review", it is implied that when all the reviews are negative, you shouldn't use that software. :)

      In other words, the system is solid, but still doesn't work if end users don't pay attention to the reviews.

    13. Re:Simple by Anonymous Coward · · Score: 0

      BTW, open source does not necessarily imply increased security. I'd rather have the word that a piece of software is secure from a professional like Bruce Schneier rather than an Open Source zealot who skimmed over a copy "Applied Cryptography" in their local Borders.

      The funny thing is, if Mr. Schneier wants to put a backdoor in that program, you're screwed, period. For exactly that reason, I figure that open source would be the only way to get real security even if open code were _less_ secure than closed.

    14. Re:Simple by Hecilwe · · Score: 1

      Also note how the "UNIX" tradition of chaining smaller, single-purpose applications together would have also prevented the problems described in this paper.

      True, but when you use multiple tools, you have to concern yourself with any temporary files created during the process. Programs like tar and bzip2 aren't designed with security in mind, and they might leave portions of an archive or the whole archive itself on disk in a temporary file. Heck, in the version of WinZip I'm familiar with, every zip/unzip process make a list of the files it zipped/unzipped in C:\winzip.log.

    15. Re:Simple by ConsumedByTV · · Score: 1

      Perhaps I am reading your statement wrong, it's a bit unclear how you phrased it.

      anyway...

      First of all, you don't as the USA, you ask an arm of it.

      Let's assume you asked the F.B.I. and if they found bugs, I bet they wouldn't tell you.

      I know that it's in their best interest to find the bugs and use them to exploit criminals in the wild, not secure bob and jane.

      An agency is a player in the game, they might act as a proxy in your best interest sometimes, but they are also a player with their own agenda.

      You cannot trust an arm that does thing in secrecy.

      Also you assume that they would look at the code and also that they have clue.

      --


      "Not my manner of thinking but the manner of thinking of others has been the source of my unhappiness." - M
    16. Re:Simple by Moraelin · · Score: 1

      "Also note how the "UNIX" tradition of chaining smaller, single-purpose applications together would have also prevented the problems described in this paper."

      Just like they made CGI web sites secure? Oh wait, they weren't. For years, Perl/CGI was _the_ way to make a site that's one big heap of vulnerabilities.

      There was no inherent problem or buffer overflow exploit in either the CGI engine of any server, nor in the Perl interpreter. The problem was... precisely clueless use of the Unix way of stringing together many small utilities. One can fill a whole tome with the bog standard exploits from that era, stemming precisely from improper use of other small programs.

      For example, since you knew that (A) they'll call a command line mailer if their site can send you mails, and (B) the clueless monkeys they hired never checked their input, it was a bog standard exploit to give the site an "email address" which would actually mail you the "/etc/passwd" file. Or, in the case of the poor buggers running as root, overwrite it. (Yes, nowadays the passwords file is shaddowed. This exploit is one of the reasons why that happened.)

      I.e., I'll have to call bullshit on that.

      Just because you have a secure function call, you don't automatically have a secure application. Regardless of whether that function call actually is a proper function call, or the function is packed as a separate small executable file and invoked via pipes/shell-scripts/whatever. The same applies: shit can still happen before it, after it, and in between. Just replacing the call mechanism won't prevent incompetent coding.

      And the Unix way only makes it more likely for shit to happen in between. You also have to be very sure of the shell's behaviour, the OS's implementation of pipes, etc.

      E.g.: Had those CGI mailer calls happened as proper C calls, nothing bad would have happened: that email address is invalid, you get an error code and that's that. But instead, true to the Unix way, it was used to build a command line to call the separate mailer. Which, because it was interpreted by the shell, opened a new can of worms: stuff you wrote in that email text field could be interpreted by the shell as extra parameters, or whole extra commands, or piping the output to/from something else, or wildcard expansions, or whatever.

      It ended up needing a buttload of parsing and validation code that wouldn't have been necessary for a plain C function call. Lots of man-hours were spent (and paid for) just to work around the defficiencies for that Unix way, in this particular situation. And in 9 out of 10 cases, they still didn't get all exploits out.

      So again: just having a funny wrapper around your secure function, doesn't magically make the whole program secure. Regardless of whether that funny wrapper is called "SOAP", "EJB", "CORBA", "VB.NET" or the Unix pipes, there is no silver bullet that will make even monkeys write secure, bug-free programs.

      (Of course, this still won't keep clueless PHB's from acting as if they wish _real_ hard, it will magically become true. They'll buy more and more soap oil wrapper, hire even less competent retards, and then wonder why it didn't work. Probably not enough of that magical snake oil. Next time let's buy more snake oil.)

      --
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    17. Re:Simple by c · · Score: 1

      Let's assume you asked the F.B.I. and if they found bugs, I bet they wouldn't tell you.

      Exactly. They'd find a bug and tell you it was secure in the hope that you'd publish it and make their jobs easier.

      Now if they tell you it's not secure, either they found a legit bug and it's something they can explain to you _or_ they think it's too secure for them and don't want you to distribute it. The latter is pretty hard to pull off unless you're the NSA and can just claim "we'd explain why it's secure, but that would reveal super-secret cryptonalysis techniques and we'd have to kill you."

      Actually, if it was too secure they'd probably try to cut a deal for a backdoor, ala Lotus.

      c.

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    18. Re:Simple by fermion · · Score: 1
      Someone else already brought up the issue of temp files....

      IMHO more serious concern is the assumption that an encryption algorithm can be fully tested without knowing the kind of data it will be fed. This is largely the same issue as winzip assuming that adding AES automatically makes the date secure. It is nearly inconceivable that pgp takes into account every variation of data. This does not mean that using existing tested tools is not better, but just that one cannot assume that a single hammer is best for all kinds of nails.

      --
      "She's a scientist and a lesbian. She's not going to let it slide." Orphan Black
    19. Re:Simple by plcurechax · · Score: 1


      Exactly. If you want to find out if your crypto implementation is secure, ask the US government. If they say yes, you've got bugs.


      Depends who in the US government you ask. Groups like the US State Department, the Dept of Commerce, CSRC of the NIST and half of the NSA (who has two purposes - one to protect against foreign intelligent threats, and one to exploit against foreign intelligent adverseries.) they want to protect most of the US public (and NAFTA, G8, and NATO interests) - including US businesses - from foreign governments. These groups can give you an idea of what is likely secure as we know in the non-classified knowledge outside the cloak and dagger world of the NSA, GCHQ, CSE, etc.

      Mind you, I'm not sure why anyone would need to ask permission to export a public standard like AES. I'm pretty sure there aren't any secrets happening there.

      AES was selected through a very open public process, so no knowledge about AES requires export permission. The US Dept of Commerce does regulate Dual-Use items (i.e. items that have a military/dangerous/hostile use and non-military use) including information security software implementations such as toolkits, libraries, and binaries (and object code). Humanly readable source code is still somewhat in disupte, but based on some US state level court cases (Phil Karn and Bernstein) it appears that human readable source code is not regulated.

  4. Predictable.. by Ckwop · · Score: 5, Insightful

    I think the problem is people approach to the security.
    They think you can just take AES and HMAC and glue them together in any way
    and arrive at security. I mean both are secure right? The result should be secure?

    Wrong! Schneier names one of the chapters in one ofhis book: "Cryptography is hard but that's just the easy part!"

    It really is very hard to secure information. It's almost intractable.. We've seen a few articles here in the last week about interesting side-channel attacks. Breaking RSA keys by listening and an earlier one which broke into computers by heating them up.

    Cryptography is littered with broken designs fielded designs like WEP and let's not mention software security..

    It's going to be twenty years before we have "trustworth computing". It would help if we could modularize cryptography like we can computer programs...

    Simon.

    1. Re:Predictable.. by sjwaste · · Score: 3, Interesting

      Yeah, its pretty sick when you can play with a previous working key and "make it fit". That might work on my 10 year old Toyota, but should NOT work on my secure data. Is this due to carelessness, though, or do we need better random generation capability to stop that threat? I remember seeing this before:

      http://www.quantum.univie.ac.at/research/photonent angle/rng/

      Basically, is it the coder's fault or the computer's fault? Maybe both?

    2. Re:Predictable.. by Ckwop · · Score: 2, Insightful

      It's a drive for efficiency..

      The head code probably said "We can save a few hundred clock cycles if we only encrypt the actual data and not the header data.. I mean what value is the header-data.. "

      BIG MISTAKE! Your a coder not a security expert. Get a security expert to make that decision - just because you write code does not give you the experience to make that judgement..

      Simon.

    3. Re:Predictable.. by Paul+Crowley · · Score: 1

      The paper makes it clear that they're combined using the correct "encrypt-then-authenticate" approach, not just thrown together. That should normally yield a secure channel so I'll be very interested to see what flaws Yoshi Kohno's found with this implementation.

    4. Re:Predictable.. by Ckwop · · Score: 2, Informative

      They missed the header data.. It's attacks based on the fact the header data isn't authenticated.

      Simon.

    5. Re:Predictable.. by sjwaste · · Score: 2, Insightful

      Unfortunately, most firms will save a few clock cycles.. err, dollars to let the coder make the decision rather than hire a security expert. :) The average manager trusts his code staff simply because he knows no better, thus wont spend extra money on a "needless" consultant.

    6. Re:Predictable.. by John+Starks · · Score: 4, Interesting

      That seems unlikely. What seems more likely is that they were trying to preserve more compatability with the Zip format by leaving the metadata unencrypted. I think everyone is being too hard on the WinZip guys. If you read at least the introduction half of the paper, you'll see that these mistakes are not completely obvious, and WinZip has been apt to correct their mistakes in the past. I suspect we'll see a new version of WinZip with these new mistakes corrected shortly.

    7. Re:Predictable.. by Paul+Crowley · · Score: 1

      There are also "key collision" attacks on the container itself.

    8. Re:Predictable.. by Ed+Avis · · Score: 1

      In other words: stick to what you know. Let Winzip do the compression and archiving, and let someone else do the encryption. WTF is wrong with making a zipfile and then encrypting it with PGP? The only reasons to put encryption in Winzip itself are fairly bogus arguments about convenience, and the chance to charge more money for a product that does more (even if it does it badly).

      --
      -- Ed Avis ed@membled.com
    9. Re:Predictable.. by dublin · · Score: 3, Insightful

      [What]is wrong with making a zipfile and then encrypting it with PGP? The only reasons to put encryption in Winzip itself are fairly bogus arguments about convenience, and the chance to charge more money for a product that does more (even if it does it badly).

      Well, let's see - after you've encrypted that Zip file with PGP, you'll be able to exchange it with all of the 0.0001% of the people in the wolrd who have heard of PGP and are willing to put up with the it. (That figure's probably not far off: As evidenced by their actual usage, the vast majority of IT professionals refuse to put up with the pains of PGP/GPG, and they're only a tiny fraction of the world's PC users.

      There are decent solutions out there - But even the best tools available, things like AxCrypt, which can be used to encrypt/decrypt any file on the fly are still considerably more of a pain than not using encryption. Encryption is not a panacea, and won't be widely used until it's totally transparently hidden by the OS.

      Arguments about convenience are not bogus: they are in fact probably the most valid arguments involved in any sort of security system discussion, since history has proven time and again that users *will* turn off or otherwise render useless any security they find to be obnoxious...

      --
      "The future's good and the present is nothing to sneeze at." - Roblimo's last ./ post
    10. Re:Predictable.. by fwarren · · Score: 3, Informative
      Arugments about convenience are not bogus;

      True, but let's look at the quote:

      Fast, Inexepensive, Easy to Understand. Pick any two

      There are always tradeoffs. The trick is to know which tradeoffs work the best for you. One set of trade offs work best for a company competing for business (or at least the company will bet on one set of trade offs paying off), while a different set of trade offs work best for a particular individual.

      When I was 12, I used a simple substituion cypher. With the following cavets:

      1. What I was encoding was probably a note to my best friend with a message like "Hey, lets talk to our moms about me spending Friday night at your house. This is great that my sister can't read this note if she finds it."
      2. I knew that any 10 year old who had 2 paragraphs of encoded text and a library book could break the code. I knew an adult who knew what he was doing could probably break it with only a sentance or two.
      3. I knew I was going to encode the note, hand it to my friend later in the day, and he would go straight home to decode it, there was not much chance of it being intercepted.
      For what I was doing, it was the best method available to me. Wrapping notes around rods, or making invisible ink, were more trouble than they were worth. We did not have 2 rods of the same size, and my expermients with invisble ink were never really satisfactory.

      Still, I have nothing really worth hiding. However, if I want to. I have the following requirements.

      1. Do the encryption on the computer, to eliminate redunancy and incrase the speed and accuracy of encryption/decryption.
      2. Use an encryption method that is currently considered secure by cryptoanlysis.
      3. Use a public/private key encryption method to simplify the process of protecting my private key and making it easy to get/distribute public keys.
      4. Use an implementation that does not swap data out to the hard drive, leave remenants of unencrypted files, etc. Things that would make the implementation insecure and easy to hack.
      5. Understand that if someone physically comes gets my computer with my passphrase on it, and I pick a weak passphrase, my infomation will no longer be private.
      6. Understand that if someone can obtain physical access to my computer and install keyloging hardware, or has the equipment to listen to frequencies from my keyboard or monitor, my information still is not secure.
      Within those parameters, I do not know of a better product than pgp/gpg encryption. Does it take work to learn. Yes, yes it does. If I want to exchange encryped information, will I probably have to teach the other person how to use it? Yes, yes I will.

      As far as even savy system administrators not using pgp. I will trust the data of 100 individuals with a secure passphrase of not getting hacked is far more likely than the possibility of those 100 administrators who do not use pgp.

      Why? For all the reasons I mentioned above. They probably feel very secure, but in reality have a weak encryption setup. It won't come back to haunt most of them, but nonetheless, it is still weak.

      People that want and really need security, will take whatever steps necessary to get it. They will live with the hassle to get that security and will be secure because of it.

      Relying on the OS to provide it makes it only as safe as the weakest link, and we have seen how many weak links there are in the OS chain. Not to mention trusting that the OS does not have any backdoors.

      Always a tradoff. So for, I have not seen a better set of trade offs for exchaning encrypted information between users than pgp. But I am open to consider better implementaions of encryption software when they become available.

      --
      vi + /etc over regedit any day of the week.
  5. Re:The following is encrypted using AES by whiteranger99x · · Score: 0, Funny

    Lqf#6Z5Q|LL5#DzGmL:$^!!AW8\wJE)hr{OMFm\\$^$]*mArkJ ^V!

    You know, I read the subject as The Following is encrypted using ASS....as in you're talking out of your ass! :P

    --
    Join the TWIT army now!
  6. How to tell if a product is secure. by teasea · · Score: 5, Funny

    Wait for a cryptographer to analyze the product, then read about it on /.

  7. Under many eyes, all bugs are trivial by proverbialcow · · Score: 2, Insightful

    So how can we distinguish between an application that simply uses the right buzzwords, like AES, from an application that is actually secure?

    Having access to the source code is a good start, so the community can examine the methods used. It's not like WinZip has my business to lose if I could compile the source myself.

    --
    The only surefire protection against Microsoft infections is abstinence. - The Onion
    1. Re:Under many eyes, all bugs are trivial by Anonymous Coward · · Score: 0

      You'll notice that they did an analysis of WinZip without any source code. Wow, who'd have believed it was possible?! This is a discussion about cryptography, not about software security. Cryptographers don't give a hoot about buffer overflows.

    2. Re:Under many eyes, all bugs are trivial by Anonymous Coward · · Score: 0

      "Under many eyes, all bugs are trivial"

      I know that this goes against the Slashdot groupthink, but that saying doesn't apply to OSS anywhere near as much as people seem to think. Info here. (PDF, 600 kB)

    3. Re:Under many eyes, all bugs are trivial by sql*kitten · · Score: 1

      Having access to the source code is a good start, so the community can examine the methods used.

      What is this "community" of which you speak? History is littered with smart people who thought they'd invented the ultimate cryptosystem, only to have to torn to shreds by a professional cryptographer. Said cryptographers spend all their time reading academic journals, not source code to consumer utilities. Being qualified to write an efficient compression algorithm or a highly usable UI doesn't qualify you to audit a cryptosystem.

      In summary, even if the source was open, it wouldn't make a difference, because there is no-one who has both the inclination and qualification to do it for free.

    4. Re:Under many eyes, all bugs are trivial by proverbialcow · · Score: 1

      What is this "community" of which you speak?

      I'm speaking of the OSS community and the crypto geek community, but mostly their intersection, a large chunk of which is the coderpunks community.

      In summary, even if the source was open, it wouldn't make a difference, because there is no-one who has both the inclination and qualification to do it for free.

      A) They implemented AES, which stood up to a great deal of scrutiny, both by professionals and crypto hobbyists, before it was accepted as a standard. It's not the crypto at fault here, it's their implementation of it. Anyone with even a basic understanding of crypto protocols (such as one gleans from reading "Applied Cryptography") would have found these holes, given access to the source.

      B) That year of crypto I took while working on a math degree doesn't qualify me? That was a waste of time, then.

      --
      The only surefire protection against Microsoft infections is abstinence. - The Onion
    5. Re:Under many eyes, all bugs are trivial by sql*kitten · · Score: 1

      B) That year of crypto I took while working on a math degree doesn't qualify me? That was a waste of time, then.

      Kid, I know people with PhDs in the field who still prefix every crypto-related sentence with something like "as far as we know..."

    6. Re:Under many eyes, all bugs are trivial by proverbialcow · · Score: 1

      I know people with PhDs in the field who still prefix every crypto-related sentence with something like "as far as we know..."

      That's because a lot of crypto is based on simply being "hard enough" to break. RSA is thought secure because, as far as we know, factorization takes O(sqrt(n)) time. It's not been proven, but since nobody seems able to do it any faster, it's assumed to be secure enough.
      LFSRs are thought to be even more secure because, as far as we know, no one knows of ANY shortcuts through them. It hasn't been proven, but again, it's thought to be secure.
      There's only so much you can learn about crypto. After that, you have to start attacking the underlying mathematics.
      Don't believe me? Ask some of your PhD friends.

      And don't call me kid, geezer. ;)

      --
      The only surefire protection against Microsoft infections is abstinence. - The Onion
  8. When I want to secure my data... by Jon+Kent · · Score: 4, Insightful

    About the last thing that comes to mind is "WinZip". Surely anyone in the least bit serious about security would look into something more mature (the implementation not the algorithm).

    Kremlin Encrypt/Decrypt comes to mind as software that I've had good experience with.

  9. stronger encryption by Anonymous Coward · · Score: 5, Funny

    We need 2048-bit buzzwords.

  10. Source code and peer review by Spetiam · · Score: 4, Insightful

    Open source is critically important with crypto, IMHO. Crypto seems to me to be something that a malicious entity would be more likely to put a backdoor into, instead of, say, an image editing program. Open source, as we all know, means that the code can be audited and compiled by a trusted party (myself), thus guaranteeing the legitimacy of the program. Perhaps more importantly, open source means the software is subject to peer review.

    1. Re:Source code and peer review by js3 · · Score: 1

      it has nothing to do with the source. Most of these are design "flaws", flaws in quotation because the makers of winzip were probably aware of this but made the decision to implement it that way for ease of use or compatability reasons. The actual AES encryption was done probably.

      --
      did you forget to take your meds?
    2. Re:Source code and peer review by westlake · · Score: 1
      Open source, as we all know, means that the code can be audited and compiled by a trusted party (myself), thus guaranteeing the legitimacy of the program.

      But only within the limits of your skill and experience. Crypto holds many traps for the over-confident and unwary.
      I distrust the popular notion on Slashdot that exposure of source is somehow equivalent to (or somehow guarantees) peer review in the medical and scientific sense of critical examination by experts in their field.

    3. Re:Source code and peer review by Spetiam · · Score: 1

      I distrust the popular notion on Slashdot that exposure of source is somehow equivalent to (or somehow guarantees) peer review in the medical and scientific sense of critical examination by experts in their field.

      Good point. I should have said that it makes peer review "more possible/likely." Generally, the only crypto softwares that I personally trust are PGP, (GnuPG) and OpenSSL. True, I haven't pored over their sources myself, but those particular projects appear to get enough attention from "the experts" to qualify as being peer reviewed.

      Just my personal opinion, but I think the greatest security shortfalls of widely accepted crypto software (PGP, GnuPG, OpenSSL, etc.) exist in how the user uses them or fails to respect other security concerns.
  11. Oh shit! by Anonymous Coward · · Score: 3, Funny

    I just designed and submitted a corporate security infrastructure built solely on zipping everything. I guess it's time to get back to community security college.

  12. Well the slashdotting is [mirror] by mirror_dude · · Score: 0, Interesting

    Seeing as winzip got slashdoted previously and I dont know if they have upgraded I put up a couple of quick mirrors:

    The mirror of http://www.winzip.com/aes_info.htm (the winzip page on AES and its implementation in winzip) is at http://mirrorit.demonmoo.com/r_476/www.winzip.com/ aes_info.htm
    The mirror of http://www.cse.ucsd.edu/users/tkohno/ is at http://mirrorit.demonmoo.com/r_476/www.cse.ucsd.ed u/users/tkohno/
    The mirror of http://www.cse.ucsd.edu/users/tkohno/papers/WinZip / is at http://mirrorit.demonmoo.com/r_476/www.cse.ucsd.ed u/users/tkohno/papers/WinZip/

    --
    Note to Mods: When I post mirrors, it's a best guess. I don't know for certain whether or not the site will go down!
  13. WinZip... by JessLeah · · Score: 4, Insightful

    ...is really the lowest common denominator of zip programs. It is what Joe and Jane Sixpack of Bunghole, Indiana use to exchange photos with their son Jake in college in Goatse, Minnesota.

    It is to archiving programs what AOL is to ISPs.

    Given that, do you really trust anything it does to be secure in any meaningful way?

    It's like if AOL announced that all AOL connections were protected using "state-of-the-art technology based on OpenSSL". Would you really trust an AOL connection to be as secure as, say, an OpenSSH connection from an OpenBSD box to another OpenBSD box?

    Just because it's buzzword-compliant doesn't mean it's actually as secure as that buzzword would imply in more geekish circles...

    1. Re:WinZip... by whiteranger99x · · Score: 1

      Bunghole, Indiana? Goatse, Minnesote? I think I'll stay away from those places...

      But honestly, using your AOL/OpenBSD analogy, all that matters to AOL (as it were) is that they bullshit their current and new subscribers into believing that some of their traffic will be safe from the big bad hackers of the world. Either way someone's laughing their way to the bank and someone's about to be 0wn3d.

      --
      Join the TWIT army now!
    2. Re:WinZip... by The+Slashdotted · · Score: 3, Interesting

      And in turn you validate one of Gates' excuses, "The larger the user base, the more attractive it will be to attack it".

      There is a difference between branding and what it does.. Wasn't AOL contributing to Firefox/Mozilla/Netscape for a short while.. Does that really make it dirty/insecure in your eyes?

      Then again, why am I trying to talk sense to an elitest?

    3. Re:WinZip... by JessLeah · · Score: 1

      Um, what? No, I'm not saying it was cracked because it's the biggest target. I'm saying it was cracked because the people who market to Joe and Jane Sixpack aren't the most brilliant programmers. (The most brilliant marketers, maybe...) Examples: Microsoft. AOL. Gator/Claria. Bonzi Buddy.

    4. Re:WinZip... by Stormie · · Score: 1

      I have no comment to make in reply to your comment - I just wanted to say that, from now on, whenever I have to fill out an obnoxious registration form on a website, my location is gonna be "Goatse, Minnesota".

    5. Re:WinZip... by Rupert · · Score: 1

      That's East Goatse, MN. Goatse is in North Dakota, as any ful no.

      --

      --
      E_NOSIG
  14. I hear a familiar mantra coming on... by jshindl · · Score: 2, Insightful

    Repeat after me:

    "Open source software is good, Closed Source is bad!"

    I feel like sometimes these stories are intended to invoke that type of response, whether warranted or not.

    A company did a bad job programming here -- no need to indite all Proprietary software on Winzip's account. :)

    -Jason/a.

    1. Re:I hear a familiar mantra coming on... by CaptainFrito · · Score: 1

      I believe you meant "indict", meaning to 'accuse, perhaps wrongly'; not "indite", which means to compose [a poem, et al]. Although some coders may disagree, I personally don't equate coding with poetry =) Unquestionably, all chants are bad, even 'open source' chants. But with respect to security, open source transparency is the best all-around approach to the security problem.

    2. Re:I hear a familiar mantra coming on... by Anonymous Coward · · Score: 1, Informative

      "A company did a bad job programming here -- no need to indite all Proprietary software on Winzip's account. :)"

      We don't have enough professors to audit all the closed software. If it *was* open source to begin with, I am sure that this problem would have been more likely to be found without professors help.

      I trust no 3rd party applications that implemenet encryption, security, or anonymous type applications honestly and competently. Always try to a F/OSS alternative.

    3. Re:I hear a familiar mantra coming on... by Anonymous Coward · · Score: 0

      do you mean indict?
      it is pronounced [In Dyte], but it is spelled slightly different

  15. Screw encryption! by ozamosi · · Score: 0, Interesting
    So how can we distinguish between an application that simply uses the right buzzwords, like AES, from an application that is actually secure?"
    We can't. Therefore we use many layers of heavy encryption. We educate ourselves to become security experts to be able to see for our selves that it really is secure. Really secure.

    Or we simply accept that everything is unsecure and uses something that seems kind of secure. Even though I hate the thought of the government watching me, I don't have anything that is so secret I need all this encryption.
  16. Not sure they're really big issues by scalveg · · Score: 4, Insightful

    Given that the WinZip people were undoubtedly trying to add "real" security without changing the way their users have become accustomed to working with the product, it seems to me like they did a pretty good job.

    The solutions to the points raised in the article as far as I can tell pretty much boil down to:

    1) Be aware that metadata of the encrypted files is not secure. (The only WinZip-specific flaw, and certainly possible to work around)

    2) Be careful how you communicate regarding the transmission of encrypted files.

    3) Be careful with your password.

    4) Check your PC every time you return to your office to make sure nobody has placed a keylogger between it and your keyboard.

    Certainly slashdot users can do that!

    1. Re:Not sure they're really big issues by Anonymous Coward · · Score: 0

      You left out "do not encrypt thousands of files with the same password." (keystream reuse)

      "Check your PC every time you return to your office to make sure nobody has placed a keylogger between it and your keyboard."

      Software keystroke loggers are much more common than hardware, and if they're going to the trouble of using a hardware-based one, they could put it inside your keyboard. If you're worried about physical security, make sure nobody untrusted has physical access to your machine.

    2. Re:Not sure they're really big issues by Anonymous+Chicken · · Score: 1

      4) Check your PC every time you return to your office to make sure nobody has placed a keylogger between it and your keyboard.

      Is that just another way of saying: you can never have too much tinfoil?

      --
      This signature is intentionally left blank.
  17. winzip is reasonably secure by js3 · · Score: 2, Informative

    most of the flaws mentioned in the article will require the attacker to go to great lengths to break the encyption. Others include the often quoted but rarely practical middle man attacks. In otherwords it is not flawed to the point where your teenage kid can hack your zip files, but the NSA could do crack it if they really wanted to

    --
    did you forget to take your meds?
    1. Re:winzip is reasonably secure by cpghost · · Score: 1

      but the NSA could do crack it if they really wanted to.

      winzip is not open source, isn't it? NSA has probably the source code, or they may have a backdoor, installed courtesy of winzip makers. Remember NSA's master key in Windows crypto libraries?

      --
      cpghost at Cordula's Web.
    2. Re:winzip is reasonably secure by Anonymous Coward · · Score: 0

      Remember NSA's master key in Windows crypto libraries?

      no, but i'd like to see your source for saying this

    3. Re:winzip is reasonably secure by NotQuiteReal · · Score: 3, Funny
      Come on, this is slashdot - you have it all backwards.

      The NSA has no backdoors into Microsoft products.

      Everyone here knows that the NSA is just a tool of Big Business.

      Clearly you meant to say Microsoft has a backdoor into the NSA.

      --
      This issue is a bit more complicated than you think.
    4. Re:winzip is reasonably secure by NumbThumb · · Score: 1
      --
      I have discovered a truly remarkable sig which this 120 chars is too small to contain.
    5. Re:winzip is reasonably secure by cpghost · · Score: 1

      Clearly you meant to say Microsoft has a backdoor into the NSA.

      Well, that is true as well, but at least, the NSA knows how to firewall their backbone (at least we hope so).

      Here's the link: Backdoor in MS crypto API (in german).

      --
      cpghost at Cordula's Web.
    6. Re:winzip is reasonably secure by Anonymous Coward · · Score: 0

      thanks

  18. Quick summary by pjrc · · Score: 5, Informative
    Here's the security problems, quickly summarized (and oversimplified). These are in the same order as the paper. The paper is lengthy and not an easy read... if you can't be bothered to RTFA, maybe this will help.

    1. Filenames, file sizes, time/date stamps are plaintext. Only the file contents are encrypted. Filenames, dates may be sensitive data (example giving, pinkslips.zip contains file pinkslip-bob.doc).
    2. Both compressed and uncompressed sizes are stored without encryption, so an attacker can know the compression ratio and perhaps infer what type of data it is based upon its compressability.
    3. File lengths are not authenticated. A man-in-the-middle attack could modify the file sizes recorded inside the zip archive so decrypting produces "garbage" output files (without warning that the zip archive was tampered). The man in the middle intercepts the communication about the problem and impersonates a request from the sender to see the "garbage". The garbage is after decryption, so if the receipient sends it in the clear, the man in the middle can easily turn it into the original plaintext.
    4. File names are not authenticated, so an attacker could tamper with the file names and change their extensions. On windows and other systems, the file name extension determines which software will be used to view the file.
    5. The CRC is stored without encryption. If an attacker suspects he knows what the message is, he can replace the ciphertext with his guess, and watch if the receipient complains about a CRC error.
    6. Zip archives can contain some encrypted files, others plaintext. They worry that a receipient may believe all or most files were protected, when only a few or one was.
    7. Key generation isn't random enough, so keys may be reused. I don't fully understand this one... maybe someone who does will reply and explain it??
    8. Attacker can create a "self-extracting" archive that mimics the GUI of Winzips, but is actually a trojan horse. They admit this isn't really winzip's problem.

    Similar to IANAL, I'm not a crypto expert. I probably botched some of these a bit, especially the key collisions one. If I've misunderstood any of these, please reply.

    1. Re:Quick summary by rsmith-mac · · Score: 2, Insightful

      While those are some interesting problems, I have to admit, they're really minor. Most of these are more social engineering attacks than technology attacks in the first place(i.e. man in the middle), and only 1, key generation, is a true technological threat to the encryption. As far as I'm concerned, even with their "flawed" implementation, this is strong enough for my needs. Anything past this calls for PGP in the first place.

    2. Re:Quick summary by AaronMB · · Score: 2, Informative

      > Key generation isn't random enough, so keys may be reused. I don't fully understand this one... maybe someone who does will reply and explain it??

      Note: i am not a crypto expert

      I've been reading up on PRNGs recently so I'll take a shot at it. The encryption method used is AES in what's known as Counter mode. The way that works is like so:

      F(X) = AES(X, SALT)

      So to get the next one in the list, all you have to do is calculate AES(X + 1, SALT). Since F(X+1) does not depend on F(X) at all, they can be done in parallel. To get the cipher text, simply XOR the plaintext with the stream.

      So X needs to start somewhere. In the WinZip specification, it starts at 0 and keeps incrementing. Thus, if you reuse a password, it'll give you the exact same sequence.

      The issue here is that they only use a 64-bit salt. Thus, you would expect that after 2^32 salts have been gone through, you'll have repeated 1. Since you've repeated one, you'll have generated the exact same sequence twice, and due to the nature of XOR, you can use that to help decrypt the 2 zip files.

    3. Re:Quick summary by Lifewish · · Score: 1

      To summarise: you don't need *the* correct password, you just need *a* correct password. There's more than one here, which is a bit of a waste. A simple example: ROT-26 encryption can be decrypted by ROT-52 encryption.

      --
      For the love of God, please learn to spell "ridiculous"!!!
    4. Re:Quick summary by alphaseven · · Score: 2, Insightful
      I agree with a lot of these criticisms. I've used Winzip encryption, the strangest thing is that instead of encrypting the zipfile, it encrypts the files within the zipfile. This is contrary to how most people expect an encryption program to work.

      I disagree that the filename should be authenticated, changing the filename should be allowed since different systems allows different characters. If I had an encrypted zipfile that I had trouble sending because the filename was too long or had spaces or something in it, I should be able to simply rename it and send it without having to decrypt and encrypt it all over again.

      The social engineering is a bit of a stretch, if someone is dumb enough to send back error files, then it would be simpler to send them a corrupt file then later ask them what password they had typed in.

      A lot of these problems could be worked around by first putting your files into a zipfile and using Winzip to encrypt that file.

    5. Re:Quick summary by AaronMB · · Score: 1

      Why not just encrypt the filenames separately? Then you'd be able to change the names in the file without having to encrypt/decrypt everything, but not without the password.
      -Aaron

    6. Re:Quick summary by iabervon · · Score: 2, Insightful

      The other flaws are differences between what is actually done and what a user is likely to expect to be done. In a social engineering attack, the attacker confuses the victem in some way; in this case, the victem is confused in advance by the software, and does something inappropriate because of that.

      The mechanism fails to provide several expected properties: that all of the information in the file is hidden and that a file which decrypts without error with a given key was created by someone with the key (and does not have modified filenames or masked data).

      The key generation attack only works against someone who generates 4 billion zip files with the same password; while a cryptographer might expect 16e18 zip files to be required, I doubt anyone is likely to actually create enough files to permit the attack. (If you create a zip file every second, you should change your password some time in the next 126 years, just to be sure).

      As it is, WinZip needs two warnings: filenames and sizes are not encrypted; and, if you get something broken out of WinZip, it might still be sensitive. The latter turned out to be a flaw in PGP as well, and it was considered sufficiently important to fix.

    7. Re:Quick summary by Bishop · · Score: 2, Insightful

      Welcome to security. The technology side to security is easier then the human side.

      Not all of those are social engineering attacks though. Modifying the header to prevent the data from being properly decrypted is a technical attacking. Data security is protecting your data from a 3rd party while ensureing that the recipient can read the data.

      Cryptographers hate poorly implemented security, especially when properly implemented security is possible. That is why this is news: People need to know that WinZip is not secure despite the "AES" feature. We the tech savvy have to let the unwashed masses know that WinZip isn't secure.

    8. Re:Quick summary by Anonymous Coward · · Score: 0

      Solution: Embed the .zip into another encrypted .zip.

    9. Re:Quick summary by Sigma+7 · · Score: 1
      I agree with a lot of these criticisms. I've used Winzip encryption, the strangest thing is that instead of encrypting the zipfile, it encrypts the files within the zipfile. This is contrary to how most people expect an encryption program to work.
      That is true, but it's effectivly the identical method used in the original versions of PKZip (2.5 or earlier.)

      A large chunk of issues listed with the security holes of the encryption method aren't specific to Winzip - it's actually a flaw with the file specification itself that is only kept for compatability reasons.

      A lot of these problems could be worked around by first putting your files into a zipfile and using Winzip to encrypt that file.
      Definatly. I'm interested about this simple trick not being mentioned. Not too suprised, since the article's attacks are more focused around the alternate routes of attack rather than the "AE-2" encryption system...
    10. Re:Quick summary by Anonymous Coward · · Score: 0

      I disagree that the filename should be authenticated, changing the filename should be allowed since different systems allows different characters. If I had an encrypted zipfile that I had trouble sending because the filename was too long or had spaces or something in it, I should be able to simply rename it and send it without having to decrypt and encrypt it all over again.

      99.999999999% of the times that the product is used, this would not be an issue. Let's not pretend like a particular feature is a good idea just because it is marginally useful .000000001% of the time.

    11. Re:Quick summary by ummit · · Score: 1
      "...If I had an encrypted zipfile that I had trouble sending because the filename was too long or had spaces or something in it, I should be able to simply rename it and send it without having to decrypt and encrypt it all over again."

      This is a user interface issue, not a protocol issue. You're right, you shouldn't have to decrypt and encrypt and send all over again. If your recipient's system can't handle your filename, then your recipient's unzipping program should give the recipient the option of renaming upon extraction.

  19. security is a system problem by staaktdenarbeid · · Score: 2, Insightful


    Security is a system problem, and requires you to look beyond the boundaries of software.

    Breaking security requires to find a side-channel, where secure information leaks through. Just when you thought you found the perfect software solution, there's some chap that starts probing your address bus or checking the power consumption profile of your processor. Darn!

  20. not everything in the paper a Winzip vulnerability by Anonymous Coward · · Score: 5, Insightful

    While most of the points raised in the paper seem valid, some done make sense. Case in point: "someone may use a keystroke logger to find out what your passphrase is". How the fuck is this a Winzip vulnerability?

  21. People should just use RAR by Anonymous Coward · · Score: 1, Insightful

    It got proper AES implementation. And unrar sources are open, so you can check how it's done. Packs much better than WinZip too.

    1. Re:People should just use RAR by Anonymous Coward · · Score: 0

      Unrar sources are outdated aren't they?

    2. Re:People should just use RAR by Sweetshark · · Score: 1

      People should just use *something*
      Is not a valid answer to a problem. Because might have a security issue or missing option two weeks later - and you will tell them:
      "People should just use *software originally having problems*."

      BTW if you go for a different solution, use one following "one tool per task" - in this case tar, bzip2 and gpg/pgp. These tools will be the standards for a specific task much longer.

  22. Old problem... by SharpFang · · Score: 1

    How to distinguish a system that is protected against viruses from one that is virus-proof?
    Some people (especially in the management) don't quite tackle the difference.

    --
    45 5F E1 04 22 CA 29 C4 93 3F 95 05 2B 79 2A B2
  23. !Complexity == Good by Graftweed · · Score: 4, Insightful

    Complexity is often your enemy when designing secure systems. It might be tempting to implement lots of features and bells and whistles and cherries on top, but if you're serious about security you'll want to keep it as simple as possible.

    Of course since when is anyone who's serious about protecting their data is going to use winzip? One tool for each job please, this is for compressing and archiving data, not to protect it. Anything else they try to build on top of it is only giving a false sense of security to people.

    I can see how "AES Encryption" must have had the marketing guys wetting their pants though.

    Stick with what you're good at.

    1. Re:!Complexity == Good by cynicalmoose · · Score: 1

      Exactly.

      The most secure cypher in the world (Vernam) is also one of the simplest. (just one XOR).

      Though I happen to believe that the Vernam cypher isn't really a secure system; it just allows you to time-delay the exchange of unsecured data.

      --
      Exercise your right not to vote. thinkoutside.org
  24. Check the community by DigitalCrackPipe · · Score: 2, Interesting

    Before I use any cryptography product, I usually check the Russian Password Crackers website, to see if there is any known attack (no link, you'll kill the site). If the listed attack is "plaintext" stay away... Yea, my assumption is that someone who knows more about cracking encryption has looked at the product, and that it has been out long enough to discover the problem. You can get the idea of what companies employ crpytographers and which ones use the word as a marketing gimmick.

  25. Yoshi's broken other things too.... by meese · · Score: 5, Informative

    Might I note that this is the same Yoshi Kohno who broke the Diebold voting system and SSH.

  26. The UNIX Way by XMyth · · Score: 3, Interesting

    Sure, it's aggrivating at times, but it leads to less implementation problems when done right. UNIX apps (and open source apps in general) seem to build off each other, so that if one thing implements its job correctly, it just calls the other app to implement that apps functionality.

    Take for example Thunderbird + Enigmail + GnuPG. It offers example of apps building on each other to add value. If Winzip had simply appealed to GnuPG or another proven encryption application then these implementation issues would have been less likely to occur.

    The tradeoff is a more compilcated install, and I guess that's where the rub is....but encrypted zip files would generally be for advanced users anyways. Sure, we want everyone to use encryption, but lets face it...the general public is a long way off from ever doing that.

    1. Re:The UNIX Way by Sircus · · Score: 2, Insightful

      ...and the reason that the general public is such a long way off is because it's not built into widely-used e-mail MUAs as a natural function. While there are certainly things to be said (though not all of those things are good) for simplicity and modularity with regard to security, until Outlook starts shipping with a standard "Encrypt this e-mail" checkbox, the general public isn't going to be using encrypted mails.

      Regarding not all of the things being good - you can't encapsulate security. That's exactly the problem in this case - they've taken a provably secure method of using an assumed-secure algorithm and applied it in a (mildly) inappropriate way, with the effect that the result is no longer as secure as one might assume. They could have taken GPG and done exactly the same thing...

      --
      PenguiNet: the (shareware) Windows SSH client
    2. Re:The UNIX Way by westlake · · Score: 1
      until Outlook starts shipping with a standard "Encrypt this e-mail" checkbox, the general public isn't going to be using encrypted mails.

      Outlook Express 6 has Sign and Encrypt checkboxes. S/MIME, 168 bit. But you need a digital ID from VeriSign ($15/yr) or another service to enable the feature.

  27. This is an educational problem by Schoony · · Score: 3, Insightful

    Security has been and always will be an educational problem. Open Source makes the problem more transparent, but it's still pretty naive to think that someone is going to do a security audit of every line of code in a given product. Ex: Linux proved this with it's kernel hacks. Regardless of the severity of the problem, they were in plain site for anyone to analyze and correct for years. More than likely someone found the holes and was free to exploit them for years until a white hat hacker made the issue public. This was just one example and equally applies to any software. The first line of defense in securing code is developer education for proper implementation of security using well known good practices. The greatest weakness that we as development professionals is that there are not enough resources available to teach these best practices, but they're coming slowly based on customer demand. I think that we all have to remember that security issues have only recently become a mainstream computing problem and coincided directly with the increase in broadband Internet connections. I.e. The last 8 years or so. So, what secure coding resources do developers have available to them today?

  28. Is this research illegal? by bigberk · · Score: 4, Interesting

    Doesn't this violate the DMCA or something? I don't want to get this guy in trouble, I'm just trying to figure out if this is the kind of research I'm allowed to pursue in an american university.

    1. Re:Is this research illegal? by Anonymous Coward · · Score: 0

      I thought the export of programs that encrypt data was against the U.S. export laws. Is this not true now?

    2. Re:Is this research illegal? by Anonymous Coward · · Score: 0

      You mean like finding out the construction flaws in skyscrapers so that the people who build them would improve on their methods and not build crumbling houses?

    3. Re:Is this research illegal? by bigberk · · Score: 1
      You mean like finding out the construction flaws in skyscrapers
      I was under the impression that (in the US and EU) it's different when you're breaking encryption to expose flaws, because the process of breaking encryption violates the widened span of copyright law made possible by WIPO (manifested as the DMCA).
    4. Re:Is this research illegal? by Starrider · · Score: 2, Interesting

      My understanding is that the research to break encryption itself is legal, but publishing a tool based on that research isn't. (Also, the DMCA only applies to encryption of copyrighted works.)

      There is considerable debate as to if an algorithm or source code is a "circumvention device", but pretty much most of the courts have ruled that object code of such a device is no longer free speech and falls under the "circumvention device" portion of the code.

      If I'm incorrect, please enlighten me as my understanding of the issue is a bit muddled as well.

    5. Re:Is this research illegal? by IncohereD · · Score: 1

      It was only ever true above certain levels (i.e. 40-bit SSL was legal, 128-bit not, 56kbps modem encoding (!) was not). I think this has been since rescinded, because you no longer get those crazy legal warnings when downloading browsers..and I don't think you can even get 40-bit versions any more.

      They were classified as "munitions" for some reason.

    6. Re:Is this research illegal? by evilviper · · Score: 1
      Doesn't this violate the DMCA or something?

      I don't see how. Research, first of all, is not a circumvention device.

      Second, Winzip's copy protection is not really a copy protection scheme, so it probably doesn't apply.

      Obviously, the thing to do is not to tip-toe around the DMCA, but to do everything you can to get it repealed.
      --
      Slashdot gets worse every day... Pipedot: News for nerds, without the corporate slant
  29. Re:not everything in the paper a Winzip vulnerabil by Anonymous Coward · · Score: 0

    "some done make sense"

    Oh the irony!

  30. Microsoft Security Problems Are Now Insightful? by Anonymous Coward · · Score: 1, Interesting

    Would have been interesting if he discussed the subtle flaws in IPSec or another more widely respected protocol.

    You don't run Windows if you care about security. Mods, do what you must, with your closed source unaudited unoperating system which is probably trojaned if you are running an illegal copy...

    1. Re:Microsoft Security Problems Are Now Insightful? by Tree131 · · Score: 1

      Linux Is Like A Wigwam - No Windows, No Gates And An Apache Inside...

  31. Re:not everything in the paper a Winzip vulnerabil by Anonymous Coward · · Score: 0

    Very good and valid point! I hope you get modded up some more.

  32. U.S. Export Laws by Anonymous Coward · · Score: 0

    I thought programs that encrypt data were against the U.S. export laws ( since people overseas can download WinZip )

  33. aespipe by EventHorizon · · Score: 4, Informative

    aespipe is a fast lightweight UNIX solution that is simpler than GPG:

    http://loop-aes.sourceforge.net/aespipe/

    Would be interesting to analyze it for potential problems; the included bz2aespipe script, at the very least, specifies the hashing and crypto algos in plaintext.

    1. Re:aespipe by Q+Who · · Score: 2, Interesting

      aespipe is a fast lightweight UNIX solution that is simpler than GPG:

      http://loop-aes.sourceforge.net/aespipe/

      There is an established UNIX solution which is not restricted to AES, and doesn't look like it's written by amateurs - mcrypt.

    2. Re:aespipe by Paul+Crowley · · Score: 1

      "aespipe" has far more serious mistakes than WinZip: the IV is not generated properly and there is no integrity protection at all.

    3. Re:aespipe by Paul+Crowley · · Score: 1

      mcrypt also appears to lack integrity protection.

      To be honest, GPG the only option likely to be secure.

    4. Re:aespipe by Anonymous Coward · · Score: 0

      Wrong. aespipe uses MD5 algorithm for IV generation and integrity protection.

    5. Re:aespipe by Paul+Crowley · · Score: 1

      That's not the impression I get from the Web pages. It's generally safe to assume tht if a software project doesn't explain exactly how the crypto is done, they've fucked it up.

  34. Do some damn research! by blitzrage · · Score: 2, Insightful

    "So how can we distinguish between an application that simply uses the right buzzwords, like AES, from an application that is actually secure?"

    Do some research and ignore buzzwords.

    --

    I have no signature
  35. Misleading!! by logicnazi · · Score: 3, Insightful

    So how can we distinguish between an application that simply uses the right buzzwords, like AES, from an application that is actually secure?


    This statement about winzip is quite misleading. Either the author didn't bother to read the paper or has an emotional bias against non-free software.

    The encryption method in WinZip is actually fairly secure, the attack mentioned in the article consists of tricking someone into sending back the decrypted output. While design improvements could be made to make this less likely this hardly qualifies as 'simply use(ing) the right busswords'. So long as you aren't an idiot and send data so confidentional you might reasonably be the victim of a complicated man in the middle attack this product will work fine for your security needs. In fact as they mention in the article PGP suffered from a similar problem.

    In fact, aside from the documented fact that the file names and lengths are in plaintext, this tool provides all the security an individual user is ever really going to need. Even large corporations are unlikely to be the victims of sucesfull man in the middle attacks and certainly anyone using WinZip for their security needs doesn't really need to worry. This is certainly enough to stop your family friends and law enforcement from reading your shit.

    I know I'm going to get jumped on by some crypto people and to be fair it *is* good we find issues like this report them and either document or fix them. However, if we are going to consider social factors (such as tricking someone into sending back 'garbage') it is only fair we credit social factors toward the credit of such a program. So we should consider the social factor that WinZip is hardly used by the government or milatary when asking if it is a reasonable security product.
    --

    If you liked this thought maybe you would find my blog nice too:

  36. Use validated software! by DangerTenor · · Score: 4, Interesting

    There are validation programs in which third party laboratories test and inspect systems related to computer security. Probably the most well known of these is the FIPS 140 program, run by NIST and recognized by the US and Canada. A friendlier description is in this FAQ.

    Another international validation program is the Common Criteria program. This provides an internationally accepted set of IT security requirements, policies, and procedures for testing.

    Use validated software. Buy validated software. Looking at software that isn't validated? Encourage them to look into the validation process. The US government can no longer purchase cryptographic modules that are not FIPS 140 validated. Put similar rules in place at your organization.

    --
    Check out our infosecurity industry blog: http://securitymusings.com/
    1. Re:Use validated software! by Antibozo · · Score: 2, Informative

      These "validations" aren't really worth much. I personally have evaluated a product that had passed Common Criteria, and I found numerous critical vulnerabilities, including flaws in basic SSL implementation, an obvious buffer overflow, the ability to access the entire supposedly protected database without authentication, etc. This was a closed-source product, so I'm sure there was a lot more that I missed, since all I did was test it for a couple of days.

      It's much better to go with open source so at least you can audit the code yourself. Saves a lot of time.

      Funny: another product I audited advertised its use of AES. As someone else pointed out, key exchange is often the problem. In this case, the key exchange mechanism used was to publish the key in plaintext after reordering the bytes, on a web page with no authentication required.

      Do not trust vendors when they tell you how secure their product is, or bandy about terms like "AES" and "Common Criteria". Most closed source products are crap -- I'm speaking from experience here -- and the vendors who know that they're selling crap just lie. If you can't get the vendor to open the source to you, you're probably better off going with someone else. If there's no other option, test the hell out of it.

    2. Re:Use validated software! by Anonymous Coward · · Score: 0

      Alas, Common Criteria (except in the US and Canada, where it requires a FIPS-140 validation) specifically does not cover crypto. You can get EAL-7 with ROT13, so long as you're honest about what it does and does not do.

  37. Re:not everything in the paper a Winzip vulnerabil by Tony-A · · Score: 1

    If someone can use a keystroke logger to find out what your passphrase is, then it is a Winzip vulnerability. That doesn't mean that Winzip can do anything about it, but the inability to counteract an attact does not make that attack go away.

  38. The difference by StarBar · · Score: 4, Informative
    between a secure program and a less secure program has nothing todo with AES. It is all about the keys. Whenever you are using symetric encryption, like AES, you need to store the key somewhere accessible both when encrypting aswell as decrypting. A human brain for instance. However at 128 bit encryption it starts to be hard to remember binary keys, even for smart folks. Then you need a secure way to store the key in, like a smartcard or an USB dongle or fetching it using PKI from a central storage using asymetric encryption like RSA. The weak point will still be the key storage and transportation, not the AES part.

    However using weaker crypto algorithms like DES will invalidate any secure keystorage simply becuase it would be much more vulnerable to brute force attacks. Using AES simply moves the weak point to another link in the chain of security for WinZIP.

    A curiousity for an example is the book "Neuromancer" by William Gibson where the AI had to trick a human beeing to unlock the last link to its pal AI because it could not be cracked by computers. A 100% computer secured old fashioned iron key! :-) I just love that chapter.

  39. Re:not everything in the paper a Winzip vulnerabil by Bodhidharma · · Score: 1

    It is a WinZip vulnerability in the same way a castle wall is vulnerable to a battering ram.

    --
    A dyslexic man walks into a bra.
  40. is 7-zip any more safe? by ManyLostPackets · · Score: 4, Interesting

    7-zip also uses AES with a 256 bit cipher key for it's password protected file option. I store my personal backups in the 7z format, as I've always had a bad feeling about WinZip's zip cipher scheme, so I wonder what issues the 7z's encryption implementation might have.

  41. We've known this about ZIP files for 15 years! by Teddy_Roosevelt · · Score: 4, Interesting

    The ZIP archive compression standard came out probably about 15 years ago (Phil Katz was a programming god despite serious personal problems), and even then it was obvious that the metadata wasn't encrypted, even with the simpler initial encryption algorithm.

    Everybody knows that if you want a secure, encrypted ZIP file, you compress the files first (with or without encryption) into a zip file called "data.zip". _Then_ you zip that file into a second, meta, zip file with encryption.

    The article points out that metadata isn't encrypted. I mean, this has been obvious for 15 years, right?

  42. Crypto is not vanilla and software is not cola. by Lord+Kano · · Score: 3, Interesting

    You can't just add an algorithm to a program and make it secure.

    It takes WORK to make a secure program. I have given a large chunk of my recent free time to get up to speed on crypto. I have been tearing through RSA Security's Official Guide to Cryptography. Basically it's my bathroom reader. The field of crypto is so complex that I doubt that the average user of WinZip fathoms more than just the basics.

    LK

    --
    "Hi. This is my friend, Jack Shit, and you don't know him." - Lord Kano
    1. Re:Crypto is not vanilla and software is not cola. by pyrrhonist · · Score: 1
      I have been tearing through RSA Security's Official Guide to Cryptography. Basically it's my bathroom reader.

      Ouch! Wouldn't toilet paper be a little softer than book pages?

      --
      Show me on the doll where his noodly appendage touched you.
    2. Re:Crypto is not vanilla and software is not cola. by Lord+Kano · · Score: 1

      I also read it when I'm soaking in the bath tub.

      LK

      --
      "Hi. This is my friend, Jack Shit, and you don't know him." - Lord Kano
  43. Re:not everything in the paper a Winzip vulnerabil by kasperd · · Score: 2, Interesting
    Case in point: "someone may use a keystroke logger to find out what your passphrase is". How the fuck is this a Winzip vulnerability?

    It isn't a WinZip vulnurability, but it is mentioned in the WinZip documentation. The exact quote from the article is:
    For example, as noted in the WinZip documentation, an adversary might try to capture a user's passphrase by installing a keyboard logger on the user's computer or might try to resurrect a plaintext file from memory.
    But the above is not the major point, it is mostly an introduction to the next point about how missing integrity of self extracting archives can be used. If you rely on self extracting archives, the archive could easilly carry the key logger into your system. So their point really is, that self extracting archives cannot be secure.
    --

    Do you care about the security of your wireless mouse?
  44. Cheap Macs? by Anonymous Coward · · Score: 0

    Instead of blaming other people for charging too much, you might try learning how to budget yourself and balance your spending with your desires. If you want something bad enough to petition for it, you should be able to adjust your savings enough to be able to afford it yourself.

    I live on about $12,000 a year, but I was able to buy a $2200 PowerBook, I drink $100/pound tea, $50 Scotch, and shell out quite a bit for my girlfriend. Just think about what you're spending money on, and whether it's really worth it to you.

    In my case, I was buying lots of shitty beer on the weekends (ah, college life), eating out when I could have been cooking, going to movies all the time, driving my 12mpg Lincoln to campus 3 blocks away, and everywhere else. All that shit adds up, and a lot of little shit, too.

    After I started cutting that stuff out, I started finding myself with fucktons of money. The first thing I set out to buy was an iBook, but then they came out with the 12" PowerBook, so I set my sights higher, waited 4 months, and bought one, fully loaded. (I sold a painting in that time that paid for the SuperDrive, but $2000 of the price came from 6 months of savings, If you can't save $1000 (for an eMac or iBook), in that time, there's something wrong with you.)

    1. Re:Cheap Macs? by Anonymous Coward · · Score: 0

      Not everybody can live in your mom's basement.

  45. Key collisions, an explanation by Gregoyle · · Score: 3, Informative

    I'm not a crypto expert either, but I've got a decent grasp on the subject.

    After reading the paper, what they're talking about with key collisions is a fairly common problem with beginning cryptosystems.

    When designing a cryptosystem, you try to get the same "bit level" of security throughout the system. The reason for this is that in most cases any system is only as strong as its weakest component (I know, duh, right). In a system using a 128 bit symmetrical block cypher (in this case AES) you are usually going for ~64 bits of "security". This basically means you can expect any successful attack to take 2^64 operations. The reason you don't get 128 bits is because of the "birthday attack"[a].

    So generally if you're using AES 128 you are going for 64 bits of security. The problem with AE-2 (the system used in WinZip), at least according to the author, is that the key generation algorithm only gets ~32 bits of security. The article just says "the key derivation process is randomized"; it does not say what algorithm is used. My guess is that they used a 64 bit algorithm to randomize they keys generated from the password.

    Since the CTR mode counter is always initially zero in this system, that means that there is no additional randomness added to the keystream (you get all your randomness from the password).

    So that part is basically saying that the system is at most half as secure as one would expect for a (well designed) system using AES 128.

    [a] The "birthday attack" is named after the "birthday paradox", which is the idea that if you have 23 people in the same room there is a greater than 50% chance that two of them have the same birthday. Where N is the number of possible choices, sqrt(N) is approximately the number of random choices made before there is a %50 chance that two of them coincide. Since in encryption you are usually using values of 2^n, this means that the "birthday bound" is 2^(n/2), e.g. if you are using encryption which normally would take 2^128 steps to find a collision, the probability of a collision is greater than %50 if you take only 2^64 steps.

    --

    "He's more machine now than man, twisted and evil."

    1. Re:Key collisions, an explanation by Anonymous Coward · · Score: 0

      It's actualy far worse than that. Most people use passwords with only 1-bit of entropy per character, forget 32-bit, this could easily be 8-bit.

    2. Re:Key collisions, an explanation by Anonymous Coward · · Score: 0

      the key generation algorithm only gets ~32 bits of security.

      No. After encrypting 2^32 files with the same password, you expect on average one keystream to be duplicated.

      This makes practically no difference at all to the level of security you get if you encrypt only a few hundred thousand files with the same password.

    3. Re:Key collisions, an explanation by Gregoyle · · Score: 1

      It also makes password/keystream guessing that much easier. It's not hard to run tests to see if a given plaintext is a recognized file format or english text.

      As I said, since the attack can be performed in fewer steps, it provides fewer bits of security.

      Your point is valid, it *also* decreases the lifespan of the password.

      --

      "He's more machine now than man, twisted and evil."

    4. Re:Key collisions, an explanation by Anonymous Coward · · Score: 0

      I don't get it. I assume you're talking about dictionary attacks, since that's the only common case I can think of where the "birthday paradox" would apply.

      In a system using a 128 bit symmetrical block cypher (in this case AES) you are usually going for ~64 bits of "security".

      I don't think so. For one thing, dictionary attacks are usually not the most feasible method of attack, so it's not reasonable to equate the general "security" of an algorithm solely on considerations of that method.

      Also, there is nothing to prevent one from using a salt of equal size to the key.

      And finally, the reduction in security caused by a smaller salt is still dependant on how many times the same password is used. The paper we're talking about says:

      "if the salt is 8 bytes long and if each user is expect[ed] to encrypt on the order of 2^32 files, then Mallory would only need to use 2^32 different salt values" in the dictionary.

    5. Re:Key collisions, an explanation by Anonymous Coward · · Score: 0

      Also, there is nothing to prevent one from using a salt of equal size to the key. ...or double it, if you're really worried that someone might have a 2^64 key dictionary and 2^64 files with the same password.

      Which would be a bit much, perhaps, given that 99% of WinZip users are going to use passwords like "secret".

    6. Re:Key collisions, an explanation by Anonymous Coward · · Score: 0

      On second thought... it's keystream reuse as well as dictionary attacks. Same basic principles apply, though.

      All the paper really says on the subject is that the salt they use is too small.

  46. Much ado over nothing? by BillX · · Score: 5, Informative

    This may be non-news to those who read the paper, but it seems like the "vulnerabilities" here are overstated. Plenty of "rah, rah, should've used open-source, all your data are belong..." comments, but successful use of any of the exploits in the paper seems highly unlikely at best.

    The vulnerabilities listed basically boil down to:

    * Filenames and sizes aren't encrypted. If you store sensitive data in the filename, it can be read. (The paper uses the example of Bob intercepting a zip file containing a file named PinkSlipForBob.doc)

    * The type of encryption method used is not authenticated. If a malicious user is able to perform a man-in-the-middle attack and edit the file so that it specifies a different (incorrect) encryption method, the final recipient will decrypt it and get a file of nothing but garbage. Now, if the attacker can also social-engineer the victim to send him that garbage file, the original file can be reconstructed.

    * File names stored in the .zip are not authenticated. Like above, if the attacker can change the file extension, (s)he can cause the file to open in the wrong application when the victim unzips that file. This will likely be a nuisance at best; while the paper states that this method could be used to mount an attack similar to the above (getting garbage decrypted by a different method), it's unclear how this would actually work (since the file decrypted successfully, and there isn't any garbage). The attacker would have to coerce the user to send the unencrypted file itself.

    * The next attack involves the attacker actually knowing the entire contents of the file (s)he wants to intercept, which to me at least, seems to defeat the purpose of intercepting it. Actually, that's a slight oversimplification: for this attack, the attacker needs to know 1 of n possibilities of what the exact file contents could be, and with this information, has a 1 in n chance of finding out if (s)he was right, by replacing the file in the archive with the "guess" (again, requiring the ability to modify the file in transit), and use the fact of whether (s)he intercepts a "Hey Bob, that zip file you sent was corrupted" message to find out whether the guess was right. (If it was a 1-byte file named "yesorno.txt", and the attacker wanted to know whether it contained "Y" or "N", this could be a useful attack. For less trivial files, however, this doesn't seem very feasible.)

    * WinZip allows both encrypted and un-encrypted files in the same archive, so the end-user doesn't know if any given file was encrypted or not. An attacker can (man-in-middle, yadayada) add files to the archive before it reaches its recipient, and the recipient won't know they're not part of the original archive. A definite flaw, however, not directly a data leak of any kind. (Although, if one of the 'unofficial files' is a keylogger, and you can get the luser to run it....)

    * A weakness in key randomization will cause a repeat key to be generated once every 2^32 files rather than the theoretical maximum of 2^64 files. So, "all" the attacker needs to do is find a victim who will use WinZip to encrypt, oh, 4.2 billion files or so, and they will have a good chance that one of the encryption keys is a repeat. Supposing there was a repeat, now they just have to know the entire contents of the larger of the two files, and they can determine the contents of the smaller one.

    The paper also briefly mentions attacks like "plant a keylogger" or "replace Winzip with a program that looks like Winzip", but I wouldn't exactly call these flaws in the AES implementation. (The paper also comes to pretty much this conclusion, and so doesn't dwell on these possibilities.)

    --
    Caveat Emptor is not a business model.
    1. Re:Much ado over nothing? by Anonymous Coward · · Score: 0

      I think the point is how the information made available by these flaws could be used by an attacker.

      For example, if the file metadata says that there's a .doc file in the archive, you know much of its contents already -- standard microsoft formatting codes.

      Another example: knowing the CRC or file size would allow you to verify guesses made by a brute-force attack. Figuring out the contents of a binary file (an image, for example) is hard. How do you know when you've got a plausible candidate? Well, if you know the encrypted file's CRC and file size, you can cut way down on the plausible candidates. Knowing the file type would help with this as well, actually, as would key collisions I think?

      I'm no crypto expert (I'm posting anonymously so as to avoid embarrasing myself) but it seems to me that with all the info WinZIP exposes, an attacker could at least cut down on the difficulty of cracking the file. Sure there's no "do this and the encryption is magically broken" type of flaw (which is what you seemed to be looking for in your analysis, incidentally) but some info about the encrypted file has to be more useful to an attacker than none.

    2. Re:Much ado over nothing? by tjboldt · · Score: 1

      I agree. Compared to the "weaknesses" mentioned in the article, there are much easier ways to take people's data.

      For example, how many people will actually use a strong password? Given the kinds of passwords most people would use, a simple l0ftcrack-style attack should give you the ZIP password within a few minutes at the most.

  47. Nothing is secure. by jonfelder · · Score: 2, Insightful

    So how can we distinguish between an application that simply uses the right buzzwords, like AES, from an application that is actually secure?

    We can't. I think it's more of a question of "Is it secure enough?" The WinZip encryption may be weak, but unless you're zipping up government secrets it's probably OK.

    Almost all encryption schemes can be broken, either through brute force or social engineering, it's just the way it is.

    Peer review certainly helps, but doesn't ensure that the product is secure. It may you tell which products are not secure, but then the above paragraph shows that.

  48. I hope've you misquoted him. by mosel-saar-ruwer · · Score: 4, Interesting

    "Don't try to create new algorithms. We know how to do that already. What we have is secure. What you need to work on is the implementation. Just because something uses encryption, it is by no means secure."

    I hope you've misquoted him.

    Personally, I know of no provably secure means of encryption and decryption [de-encryption]. I know that it is widely believed [although I don't know whether an infrastructure is in place within which it could be proved] that one time pads are secure, but I don't know of anyone who's proposed a way secure means for the distribution of one-time pads, and, for that matter, there's a rather old and rather contentious controversy as to whether one-time pads can even exist in the first place [Google on God does not play dice with the universe].

    As for the standard encryption and authentication techniques, to the best of my knowledge, it is still an open question as to whether there are holes in Rivest-Shamir-Adleman; specifically, to the best of my knowledge, it is an open question as to whether third-party decryption of Rivest-Shamir-Adleman is as hard as the factorization problem itself.

    And even if you assume that third-party decryption of Rivest-Shamir-Adleman is as hard as factorization, it is still, to the best of my knowledge, an open question as to whether factorization is a hard problem, at least on classical Tukey/von Neumann machines. [It is known that factorization is not necessarily a hard problem on a class of theoretical machines which do not yet exist in practice.]

    So anyone who says "What we have is secure" is either incompetent to practice in the field [which, I suppose, does not necessarily determine the competency to teach about the field] or has been misquoted.

    To the contrary, anyone who is honest about the state of affairs within the community of encryption artists will tell you, "We have a collection of algorithms that are widely believed to be secure, but I can no more prove to you that they are secure than I can, for instance, offer you a proof of The Existence*."

    [*FYI: It is a little-known fact that Kurt Gödel believed he was in the possession of a proof of The Existence towards the end of his career...]

    1. Re:I hope've you misquoted him. by Karhgath · · Score: 1

      Well,for one-time pad, the logistics is the hardest as you've stated. However, if implemented correctly and as soon as it becomes more viable, quantum key distribution QKD will alleviate all problems of key distribution. However, I don't see it used mainstream in the next 10yrs, but it could be used by the govt and things like that in less than 10yrs IMHO.

      With no way for someone to eavesdrop the key or without showing any vulnerabilty to known types of attack(timed, man-in-the-middle, etc.), it's going to be a pretty secure one-time pad implementation, with MUCH less logistic problem(albeit there still are some limitation, so probably forget about mainstream before a long while). It's still said to be unconditionally secure, and AFAIK, it's gonna take something else we didn't discover/thought of yet to be able to conclude otherwise.

    2. Re:I hope've you misquoted him. by crypto257 · · Score: 1

      The point is if it hasn't been proved un-secure, you at least have some hope that it's ok. The problem usually isn't the algorithms involved but the weak factor in any security system, those impossible humans. They leak information about passwords, behaviours, and intentions all the time. Nothing in cryptograpy can help if the message is "do the deed" and both parties are known in advance.

    3. Re:I hope've you misquoted him. by God!+Awful+2 · · Score: 3, Interesting

      That was just one of those typical comments that fits the mould of an insightful comment, but really isn't. See below.

      I hope you've misquoted him. Personally, I know of no provably secure means of encryption and decryption [de-encryption].

      And now you're misinterpreting him as well. "Secure", "provably secure", and "perfectly secure" are three different things and *YOU* seem to have trouble with the difference. The OP's prof is talking good sense. When it comes to cryptography, companies should stick with using the best common practice rather than trying to invent their own. It's the exact same advice you would get from Schneier.

      I know that it is widely believed [although I don't know whether an infrastructure is in place within which it could be proved] that one time pads are secure

      One-time pads *are* provably perfectly secure (in a cryptographic sense), but they are irrelevant in almost every practical application of cryptography. And yet every two bit amateur cryptographer on /. (i.e. someone who has read an edition of Crypto Gram) will mention them at every possible opportunity. This may appear to prove their knowledge, but it actually demonstrates their ignorance.

      As for the standard encryption and authentication techniques, to the best of my knowledge, it is still an open question as to whether there are holes in Rivest-Shamir-Adleman

      See this is where you really pissed me off and goaded me into replying. 99% of the people reading your comment already know what RSA is. 90% of them probably know that it stands for Rivest-Shamir-Adleman, but no one actually calls it that except for pretentious wankers who want to appear smart.

      -a

    4. Re:I hope've you misquoted him. by alex_tibbles · · Score: 1

      AFAIIA...
      Two points: 1) there are proofs of security, I believe, but all such proofs are proofs of relative security. I.e. that cracking algorithm X with key length Y is at least as difficult as eg. factoring a prime of length Z. (I'm sorry not to provide a reference here. Anyone?).
      2) The nature of the universe regarding determinism, is irrelevant to the existence of One Time Pads. The kind of randomness involved is not the type of whether some omniscient being could predict the values of the pad, but whether a (non-omniscient) attacker either a) can determine a pattern within the pad and usefully predict from that, or b) knowing the means of creation of the pad, can replicate the values of the pad.
      In order to prevent (a), the pad creator must use a source of information that is sufficiently lacking in structure so that any structure that does exist does not exhibit itself within the lenght of the pad. Properties that depend on microscopic structure of materials here are commonly used, since the phase space is so incredibly vast (much larger than the length of any possible pad).
      Again the chaotic nature (i.e. the sensitivity to initial conditions) of bodies about thermal equilibrium might make good sources for pad since even if an attacker replicates the pad creation equipment, no matter how close the initial conditions, there will be a point after which the replica diverges from the original, and only the first portion of the pad would be compromised.

    5. Re:I hope've you misquoted him. by merlin_jim · · Score: 1

      I know that it is widely believed [although I don't know whether an infrastructure is in place within which it could be proved] that one time pads are secure,

      If the pad is random then it is secure. As long as the best way to recreate the pad is by randomly guessing until you happen to hit on it, then the pad is secure. The security of a one time pad comes from the fact that it can't be duplicated. And there are tests for how regular or random a particular piece of data is...

      but I don't know of anyone who's proposed a way secure means for the distribution of one-time pads,

      Well there's the tried and true method of carrying the pad to the destination. Banks are using quantum cryptography to make one time pads to exchange session keys for traditional encryption. There's two secure distribution methods

      and, for that matter, there's a rather old and rather contentious controversy as to whether one-time pads can even exist in the first place

      I don't know if you've heard, but quantum mechanics is pretty well proven these days. Atomic events really are random and probabilistic in nature. There are well known ways to collect random atomic events and make a one time pad out of them. I'm not going to argue whether anything is truly "random"... that doesn't matter. What matters is that its chaotic enough to be indistinguishable from random, and there's ton of stuff that is...

      As for the rest of your concerns, they are right on... encryption analysts should be concerned with accurately representing their field. However, that doesn't mean you have to caveat every expression either. RSA has been extensively reviewed and is believed to be secure, except for a few known holes that are easy to close in the implementation (most of them have to do with keys that are easily guessed)

      Even better, there are encryption algorithms that ARE provably correct. We don't yet have a general way to prove any crypto system secure or not, but for special cases we can do it (the most important criteria is that the keystream is reversible in the implementation; that is, that, given the entire state of the system one can go forward or backward in the keystream arbitrarily)

      So there are options. And, as always, a bigger keyspace is better. I'm pretty confident that, if they haven't found a glaring hole in RSA yet, any future holes will be minor, and that having a larger keyspace will therefore make it more difficult to crack in any case...

      --
      I am disrespectful to dirt! Can you see that I am serious?!
    6. Re:I hope've you misquoted him. by Anonymous Coward · · Score: 0

      1. A one-time pad is unbreakable, at least in the mathematical theory. The reason? It is used only once. There ya go.

      2. The DOD has addressed secure distribution of keys for years upon years. It is part of a program of layered defense, which incorporates all the elements of personnel security, procedural security, physical security, operational and communications security. Security, as mentioned time and again in nearly every Information Assurance book, forum, or discussion, is a process. Always has been, always will be. Good observation.

      3. Algorithms themselves are only part of the security equation - the key is, well... the key. Work factor is everything in encryption and simply adjusting the number of rounds or steps your data has to negotiate into the X0R is only part of the equation. You may double that effort and still get the same work factor.

      Case in point? DES encryption. When DES was cracked, research was done on running double the number of rounds, hence, in theory, doubling the work factor.

      As it turns out, the work factor for DES and 2DES is the same. Only by tripling the rounds do you get the increase of work factor, thereby increasing your encryption. 3DES is still in use today as it provides a reasonable bulwark against attacks.

      4. By the way, for those tin-foil hat wearers, NSA does not need a back door into Windows or any encryption set - just a building full of big-ass Crays will do nicely.

    7. Re:I hope've you misquoted him. by God!+Awful+2 · · Score: 1

      If the pad is random then it is secure. As long as the best way to recreate the pad is by randomly guessing until you happen to hit on it, then the pad is secure.

      Arrgh... The same thing explained wrong twice in the same thread. The perfect/provable security of a one time pad is that you *can't* keep guessing until you happen to hit on it. Since for a given N-bit ciphertext, there exists some N-bit key that maps to *any* N-bit plaintext, there is no way to distinguish a correct answer from an incorrect one.

      Even better, there are encryption algorithms that ARE provably correct. We don't yet have a general way to prove any crypto system secure or not, but for special cases we can do it (the most important criteria is that the keystream is reversible in the implementation; that is, that, given the entire state of the system one can go forward or backward in the keystream arbitrarily)

      I don't even know what that means!

      -a

    8. Re:I hope've you misquoted him. by merlin_jim · · Score: 1

      The perfect/provable security of a one time pad is that you *can't* keep guessing until you happen to hit on it. Since for a given N-bit ciphertext, there exists some N-bit key that maps to *any* N-bit plaintext, there is no way to distinguish a correct answer from an incorrect one.

      And thus my statement "As long as the best way to recreate the pad is by randomly guessing until you happen to hit on it, then the pad is secure"

      In other words, as long as there is no way to determine the OTP than to try every single possible N-bit pad, then it is impossible to determine which one is correct.

      As for the other part, let me say that there are secure algorithms that have been proven to be secure. I'm not an expert; I don't know precisely what that means. I do know that it means that someone has taken a mathematical look at it and determined that certain assumptions on which the crypto system relies on are actually true.

      The method to prove a cryptosystem relies on its keystream to be reversible. We don't yet have a method to prove any cryptosystem, only ones that have a reversible keystream. Thus I am inclined to believe that the proof relies on the mathematical principle of induction or some similar principle. So there are some cryptosystems that have been proven to be secure as long as certain base assumptions hold (i.e. the shortest time to factor a number is n log n, etc)... the original poster was saying that RSA hasn't been proven secure and therefore all crypto systems are hash.

      --
      I am disrespectful to dirt! Can you see that I am serious?!
    9. Re:I hope've you misquoted him. by God!+Awful+2 · · Score: 1

      And thus my statement "As long as the best way to recreate the pad is by randomly guessing until you happen to hit on it, then the pad is secure"

      In other words, as long as there is no way to determine the OTP than to try every single possible N-bit pad, then it is impossible to determine which one is correct.

      Well, I happen to disagree that those two statements are equivalent. The first one sounds like the pad can be cracked by brute force.

      As for the other part, let me say that there are secure algorithms that have been proven to be secure. I'm not an expert; I don't know precisely what that means. I do know that it means that someone has taken a mathematical look at it and determined that certain assumptions on which the crypto system relies on are actually true.

      Yes, I'm aware of these security proofs. You can prove things about any cryptosystem, not just those with "reversible keystreams". Of course this stuff is fairly subjective. Generally the axioms for the proof are more specific than you the examples you gave. E.g. "Assume that P is an ideal random number generator."

      But I am a bit puzzled by your terminology. I have never heard of a "reversible keystream". A google search for "reversible keystream" returns no hits (although there are 153 instances of those 2 words occuring in the same document.

      -a

  49. Oops - Tukey/von Neumann == Turing/von Neumann by mosel-saar-ruwer · · Score: 1


    Sorry, I seem to have a mild case Fourier analysis on the brain.

  50. Pssssst: GnuPG by Futurepower(R) · · Score: 1


    Secure WinZip: Put files together with WinZip. Then run The GNU Privacy Guard.

    1. Re:Pssssst: GnuPG by Krunch · · Score: 1

      Better just use GPG since it compress files too (by default it will use the same compression algorithm than Winzip). If you want to encrypt several files, use tar ( availiable for Windows too) before.

      --
      No GNU has been Hurd during the making of this comment.
  51. Re: When I want to secure my data.. by wirelessbuzzers · · Score: 1

    Personally I use GPG. It's open source, has lots of users, and is very intensely reviewed.

    However, if you're sending an archive to a Windows user, and you trust your archiver's encryption, why would you want to mess with some external tool? They quite possibly don't have PGP or Kremlin or whatever, and they do almost certainly have WinZip. It's simpler just to check the relevent options there instead of running it through some other program.

    Of course, in any of the various Unices, it's as simple as tar -czf- files | gpg --encrypt.

    --
    I hereby place the above post in the public domain.
  52. It's like safety by karlandtanya · · Score: 1
    Security is like safety. You have to do some serious analysis of the whole situation before even thinking about going out and purchasing lightscreens and control-reliable relays.

    Same thing with security. Simply downloading and installing the "latest security tools" does NOTHING except give you warm and fuzzies.

    --
    "Reality is that which, when you stop believing in it, it doesn't go away." - Philip K. Dick
  53. std. disclaimer by tomstdenis · · Score: 2

    I think Bruce is a smart and clever fellow and he certainly knows what he's talking about.

    However, I think *any* cryptographer will say "crypto is hard". Just like *any* heart surgeon will say "transplantation is hard."

    Why people continually attribute such obvious tidbits of truth to him is beyond me. Here's a tip for you non-cryptographers out there.... Bruce isn't even an academic cryptographer!!! There are way smarter [Lenstra, Daemen, Matsui, Biham] cryptographers out there. If you want to quote cryptographers at least quote ones that have new and original things to say instead of the repetively tiring press-whore Schneier.

    Tom

    --
    Someday, I'll have a real sig.
    1. Re:std. disclaimer by Anonymous Coward · · Score: 0

      However, I think *any* cryptographer will say "crypto is hard". Just like *any* heart surgeon will say "transplantation is hard."

      Wow, what a profound statement. Heart surgeons couldn't be saying "transplants are hard" because transplants really are hard; they must have an agenda.

      Of course, all the evidence (including this evidence) showing all the myriad ways people (even cryptographers) screw up doesn't have anything to do with an assessment that crypto is hard, does it?

      But sure, I'll believe you -- on one condition. Go get your next heart transplant from an auto mechanic. After all, how hard can it be?

    2. Re:std. disclaimer by Spiked_Three · · Score: 1

      I know from first hand experience, Bruce will say whatever Bruce is paid to say. Anyone care to speculate who and why he was paid to dis WinZip?

      --
      slashdot troll = you make a compelling argument I do not like the implications of.
    3. Re:std. disclaimer by tomstdenis · · Score: 1

      I think you misunderstood my post.

      I was stating that "crypto is hard" is an OBVIOUS statement for any cryptographer. Heck, even before Schneier entered the scene crypto was hard.

      My point is I'm tired of seeing Bruce being portrayed as genius for saying things like "you can't just pluck a cipher and make a secure system" or "crypto is hard" or ....

      There is a reason why the distinction as "snake oil" exists.

      Tom

      --
      Someday, I'll have a real sig.
    4. Re:std. disclaimer by tomstdenis · · Score: 1

      Don't get me wrong he's a keen guy to listen to [when the listening is free]. In as much as a comedian is funny to listen to.

      As for being paid to dis WinZip it's so he can get his two little buzzphrases out there and plug his stupid company some more. He probably has a string on his back with a hoop attached that you can pull to make him say such neat truths.

      [pull] The cryptographer says analyze your threat model.

      [pull] Picking ciphers is the easy part.

      [pull] Buy stocks in Counterpane.

      [pull] Cryptography is uber-hard. Pay me money.

      [pull] Conference talk? Sure 20,000$ in expenses.

      [pull] I can't code but have a degree in comp.sci nonetheless.

      [pull] It's like the south-mongolian traffic system, [long story], and that's why you see modem lights on cable modems. ;-)

      Tom

      P.S. this was supposed to be "all in good fun". I'm not trying to belittle Bruce.

      --
      Someday, I'll have a real sig.
    5. Re:std. disclaimer by MikeBabcock · · Score: 1

      The problem seems to be that people don't realize that crypto is hard.

      Everyone seems to be aware that they only let an actual heart surgeon do heart surgery.

      It doesn't seem that people know they should get only cryptographers to do cryptography.

      --
      - Michael T. Babcock (Yes, I blog)
    6. Re:std. disclaimer by tomstdenis · · Score: 1

      Maybe but I think for the most part people "do your own crypto" for simple reasons

      1. They don't know better

      2. They're cheap

      3. They're trying to get out the door quick as possible.

      Mostly developers should know better [e.g. know that you don't know]. So it falls into #2 or #3.

      Look at Mythic for instance. Their first authentication protocol was broken. So what did they do? Hash it out again only to get broken again. They're just cheap. I'm sure mythic knows crypto is hard they just hope the users don't.

      The best service Bruce did was breaking protocols. He didn't break WinZip so really why does he have a fucking say in this at all? When he broke ORYX or CMEA I'd say he's entitled to a bit of press. But he's just milking it now.

      Sure crypto is hard, I think the dude who broke WinZip should be the one saying it though not Bruce.

      Tom

      --
      Someday, I'll have a real sig.
    7. Re:std. disclaimer by Spiked_Three · · Score: 1

      Yeah, I mean he's a smart guy and all, and smart guys know how to make more money. The only thing I could think of was he's still mad his blowfish didnt get picked for AES. But surely there's better targets than WinZip. Some of the scenarios in his paper border on rediculous. Not that they aren't true, but they would apply to any algorithms, including his own.

      --
      slashdot troll = you make a compelling argument I do not like the implications of.
  54. You do what MS-Whitehouse does. by dilvish_the_damned · · Score: 1

    You ask Howard Schmidt. He will tell you.

    --
    I think you underestimate just how much I just dont care.
  55. the keystream reuse problem by Anonymous Coward · · Score: 0

    The salt is generated randomly. There are 2^64 possible values. If you happen to get two files encrypted with the same password, using the same salt, then the transformation done to encrypt them is the same. If you know the plaintext of one of them, then you can easily decrypt the other (up to the length of the first).

    Also, you may have a somewhat easier attack to decrypt both of them than you otherwise would; but I think it still wouldn't be particularly easy, since the data is compressed.

    This is a realistic problem only if you encrypt millions of files with the same password.

  56. misdirected criticism by hak1du · · Score: 4, Informative

    From a quick glance through the paper, it doesn't sound like he found any smoking guns. The attacks he thinks of are pretty unlikely, and he did not find anything that makes the method intrinsically insecure.

    WinZip seems to do what it claims it does: encrypt file contents with AES, no more and no less. Yes, it leaves the "metadata" unencrypted, such as it is, but so what? You get the same kind of behavior when you use the AES command line utility on UNIX. Nobody ever said that it would protect metadata, and it should be pretty clear to users that it doesn't as soon as they open the WinZip archive and see the file names. Furthermore, protecting the metadata through encryption would decrease usability significantly.

    We also know that shredders don't offer perfect security, but they are sure a lot better than just throwing out documents on the curb. Well, it's the same with cryptography. The sooner people like Schneier realize that and stop scaring people away from cryptography by making obscure points, the better off we all are.

    1. Re:misdirected criticism by Anonymous Coward · · Score: 0

      Actually the algorithm WinZip is using also does an authenticity check. So you not only know that it's encrypted, but you should also know that whoever gave you the file also had the secret key. The problems he talks about in the paper reflect the fact that while winzip is likely keeping the secrecy of the information (except for the key generation issues), it is not providing a good authenticity check.

      The fact that someone without the secret key can take an encrypted file and modify it without the recipient getting a message letting them know it was modified is a *bad* thing. Perhaps the examples given in the paper were contrived, but this is a very significant error on the part of the designer of the protocol.

  57. these people wouldn't like UNIX either by hak1du · · Score: 1

    This guy didn't find any problems with the AES encryption per se, he just doesn't like the way it is used. But the same objections he has to WinZip would apply to using PGP or AES command line tools, either for files on disk or inside tar archives.

    WinZip seems to do what you expect it to do: it encrypts each file individually using AES. That's a perfectly reasonable thing to do, and that's all there is to it. It's the objections that are bogus, not WinZip.

  58. "Insightful?" by Anonymous Coward · · Score: 0

    Thank you professor obvious. Next, please point out that AOL is not for the technically savvy, and that emailing the same Really Funny .exe to 300 people isn't very swift.

    +1 what a freaking brilliant insight, ooo ooo!

    We are all in debt to you for your huge contribution to society with this post.

    P.S. you insensitive clod.

  59. Pretty Common Problem by pympdaddyc · · Score: 1

    This is pretty much (in a very general sense) exactly how the Xbox was hacked. I mean, it makes complete sense right? It doesn't matter how good the lock on your door is if you can just smash a window and get the key.

  60. Him, again! by exp(pi*sqrt(163)) · · Score: 1
    how can we distinguish between an application that simply uses the right buzzwords, like AES, from an application that is actually secure?
    I don't know, but I'm sure it requires us to pay homage to Schneider.
    --
    Doesn't it make you feel good to know that our freedoms are protected by politicans, lawyers and journalists.
  61. Re:not everything in the paper a Winzip vulnerabil by Anonymous Coward · · Score: 0

    Case in point: "someone may use a keystroke logger to find out what your passphrase is". How the fuck is this a Winzip vulnerability?

    Well, for example, Winzip could (but doesn't) provide a "secure entry mode" which was based on an on-screen mouse-driven "keyboard" with a randomised key layout. Or it could check the process list for known key-logging programs and alert the user if any are detected. Sure, neither method is foolproof, but at least it would be making an effort...

  62. nonsense by Anonymous Coward · · Score: 0

    Actually the algorithm WinZip is using also does an authenticity check. So you not only know that it's encrypted, but you should also know that whoever gave you the file also had the secret key.

    Does WinZip promise that those authenticity checks are cryptographically secure? I kind of doubt it; the CRC feature just looks like the traditional CRC check that WinZip always used to have, mostly guarding against accidental errors.

    The fact that someone without the secret key can take an encrypted file and modify it without the recipient getting a message letting them know it was modified is a *bad* thing.

    No, it's not. It's a trumped up threat of little practical significance, which is why all the examples in the paper seem contrived--they are contrived.

    It looks to me like the WinZip authors just added AES encryption in a straightforward, unsurprising way. It does what it does, and what it does looks useful to me. If you want it to do more or something different, that's not a problem with the software--you just picked the wrong tool for your needs.

  63. Secure enough for most. by dtfinch · · Score: 2, Informative

    An attacker won't be able to extract the contents from your zip files without your assistance.

    To summarize their main concerns:
    * The file listing is not encrypted, allowing attacker to see file names, sizes, compression ratios, and dates.
    * The files are encrypted using an AES based stream cipher, whereby if the attacker replaces the encrypted contents, gets you to decrypt them, and gets a hold of the decrypted garbage that resulted, they can use the "garbage" to decrypt the original.
    * An attacker can rename files in the zip.

    The only one that reveals the contents of your data requires a bit of social engineering to get you to decrypt a chosen ciphertext and send them the result. Without tricking you into helping them, all an attacker can do is get a file listing, which may not be useful if they already knew what they were after.

  64. Windows XP supports Zip files. by Futurepower(R) · · Score: 2, Interesting


    In Windows, it is better to use WinZip, since so many people are accustomed to it. Also, Windows XP supports Zip files, but not tar.

    Gnu Privacy Guard is the most peer-reviewed of the encryption programs, I think.

    The goal is usually to transmit one compressed file safely that encloses all the files needed to be transferred, and then use those files from within the enclosing compressed file. The value of WinZip is not just in compression, but in providing 32-bit CRCs that WinZip uses to give error messages if files are corrupt. If there are no error messages after testing with WinZip, then we know the transfer was successful.

    Another factor that is sometimes useful is that WinZip also supports TAR and other methods of compression and binding files together.

    1. Re:Windows XP supports Zip files. by cynicalmoose · · Score: 1

      Yes, but WinZips support of tar.gz files is pretty rudimentary, because it can't elegantly decompress and then untar like tar xvzf can.

      --
      Exercise your right not to vote. thinkoutside.org
    2. Re:Windows XP supports Zip files. by YouMakeMeSoANGRY · · Score: 1

      Gnu Privacy Guard is the most peer-reviewed of the encryption programs, I think.

      Even that doesn't make it invulnerable to implementation problems. The implementation of ElGamal signatures in GPG was broken for FOUR years! (Previously mentioned on slashdot, see here for the actual paper presented at this years EuroCrypt). The fix for this problem in the latest version of GPG? Remove that option.

      As the author of the paper said, availability of source code may well be a necessary condition for detecting flaws in cryptographic software but it certainly isn't sufficient!

  65. Winzip 9 has FIP 140 validtion by Bunyip+Redgum · · Score: 1

    Winzip 9 has FIP 140 validtion and the algorithm used is open source!
    see: http://www.winzip.com/aes_info.htm
    It is the implementation that has been found wanting.

    1. Re:Winzip 9 has FIP 140 validtion by DangerTenor · · Score: 1

      Winzip 9 does not have FIPS 140 validation. If it did, it would be on this list.

      FIPS validation is intended to ensure the cryptographic mechanisms, including key management, are done properly. Validation doesn't stop every poor implementation, but it is a start.

      --
      Check out our infosecurity industry blog: http://securitymusings.com/
  66. Patriot Act not withstanding... by NotQuiteReal · · Score: 1
    Serious question - I think it is quite possible that export versions of software [from every country to any country] most likely have state sponsored backdoors installed. Does anyone know anything about this, or did y'all sign some NDA in blood?

    In today's environment, I assume, even domestic software in the USA may have government suggested features as well, not that other countries haven't had it all along.

    In my opinion, nothing has changed for decades, except the technology; e.g. if you are a "bad guy", they will find some way of watching you, if you are bad enough. For the tin-foil hatter's out there... consider this - there are too damn many people doing too damn much stuff for them to watch everone. Don't worry about it too much.

    --
    This issue is a bit more complicated than you think.
    1. Re:Patriot Act not withstanding... by Anonymous Coward · · Score: 0

      you mean like those flawed intel? chips that were shipped via a contracter to the USSR .

      ahhh i envy the cold war days.

      that was a very slick move and is reminscent of the old spy vs spy stuff. what a time

      (google for the accurate info on that exploit, it rocks)

    2. Re:Patriot Act not withstanding... by cpghost · · Score: 1

      That would be a lot of software to backdoor! As you've said, it is impossible to watch everyone 24/7/365. It would also be extremely difficult to force every software shop to install backdoors either in domestic or export versions. If you want to do this, you have to coerce either library/toolkit vendors or even operating system vendors to put backdoors in for you. And this means stuff like crypto libraries, kernel modules etc. I'm quite sure that most software vendors are honest and not very keen about helping their government spy on their customers.

      --
      cpghost at Cordula's Web.
  67. Common Certification Criteria anyone ? by Anonymous Coward · · Score: 0

    With network firewalls and other such software there are already recognised processes for getting evaluation and certification for security related products. This involves some cost to the vendor, as they obviously can't certify their own products.

    What appears to be needed is a drive from business/government to give priority to any such products, unless there is a sensible (auditworthy) reason to choose another uncertified product and formally acknowledging the disks involved.

    This works for firewalls, and at a minimum provides a limited form of peer review. If purchasers could examine the evaluation criteria applied to a particular product, and match the independant findings against their particular circumstances, business and government can have a greater level of confidence in the product.

    If 'joe public' then has to choose between a product that has some form of independant certification, and another that business and govermnet don't want to touch, which will they choose ?

  68. Fundamental software engineering problem... by AtomicBomb · · Score: 2, Insightful

    Many software houses cannot get the security right for their products. There must be some unique problem upon this.

    First, it is the testing problem. For most features, e.g. number of request handled by a database, compression ratio of a video encoding software, the correctness of an accounting package, the test is easier to construct than the software itself. For security related enhancement, the difficulty is about the same (similar applies to stability).

    Second, it is the actual developing problem. For most small/medium size software house (except the security related ones), I doubt if they have specialist who knows security/ encryption of that kind of stuff. One day, when the PHB wants some more security feature in the product, he would most likely deploying some programmers skilled in other areas to work on this. Obvious, it won't work that well....

  69. Errata... by Anonymous Coward · · Score: 0

    The abstract begins with "WinZip is a popular compression utility for Microsoft Windows computers"; the word "-infected" is missing.

  70. Replying to myself by alex_tibbles · · Score: 1

    Re: 1): (from TFA) M Bellare and C Namprempre "Authenticated encryption: Relations among notions and analysis of the generic composition paradigm" in T Okamato (ed.) Advances in cryptology - ASIACRYPT 2000, volume 1976 of Lecture notes in Computer Science pp 531-545. (Springer-Verlag, Berlin Germany Dec. 2000).
    "The underlying AES-CTR-then-HMAC-SHA1 code is a provably secure authenticated encryption scheme per results by Bellare and Namprempre."

  71. How to tell by Anonymous Coward · · Score: 0

    So how can we distinguish between an application that simply uses the right buzzwords, like AES, from an application that is actually secure?

    Perhaps the first question to ask is: Does it run on Windows?

    1. Re:How to tell by Anonymous Coward · · Score: 0

      Would you mind explaining how that flippant comment has anything to do with actually answering the question?

      Or are you just YASR? (Yet Another Slashdot Retard)

  72. And I hope he didn't. by Just+Some+Guy · · Score: 1
    I hope you've misquoted him.

    I hope that he meant every syllable of it. Here's the deal: the list of people in the world smart, paranoid, and experienced enough to develop a new, relative secure crypto system is extremely short, and the odds of one of them being in a random classroom at a given moment is almost nil.

    RSA may be breakable. 3DES may be breakable. We may even learn currently "impossible" methods of breaking quantum crypto. However, that professor can be reasonably confident that noone who was in his classroom when he said that is going to write a more secure system.

    Honestly, if anyone in that room is gifted enough in that extremely small problem space, then they probably already know it and a professor speaking to the contrary isn't going to dissuade them. On the other hand, someone who thinks that they may be smart enough to create the Next Big Thing in crypto may remember their teacher's words and give up on the idea after being laughed off of sci.crypt a few times after their algorithms are shredded by people who know the subject better than they do.

    If that professor can convince one would-be crypto hack to do something more productive with their time, then the world will be a better (and more secure) place for him having done it.

    --
    Dewey, what part of this looks like authorities should be involved?
  73. passport identity info and encryption? by MMHere · · Score: 1

    So what about the "security" measures being used to protect RF-transmitted passport info/photos that are being introduced for US passports?

    What are they using, and who is providing it?

    This was mentioned a couple of days ago on /.

  74. I don't get it by Pan+T.+Hose · · Score: 1

    Filenames and sizes aren't encrypted. If you store sensitive data in the filename, it can be read. (The paper uses the example of Bob intercepting a zip file containing a file named PinkSlipForBob.doc)

    Wait a minute. But Bob is exactly the person who is supposed to read the cleartext in the first place, is he not? Now, if Eve could intercept said zip file, then she would be able to tell Mallory about it and this would most certainly be a very serious problem. But why on Earth would Alice be worried about Bob reading the cleartext is simply beyond me.

    --
    Sincerely,
    Pan Tarhei Hosé, PhD.
    "Homo sum et cogito ergo odi profanum vulgus et libido."
  75. Re:Hidden encryption by MoFoQ · · Score: 1

    that's called stenography