Slashdot Mirror


Gmail Drops Support for Connecting To Pop3 Servers With Self -Signed Certs

DECula writes "In a move not communicated to its users beforehand, Google's Gmail servers were reconfigured to not connect to remote pop3 servers that have self-signed certificates, leaving folks with unencrypted connections, or no service when getting email from other services. Not good for the small folks. One suggestion was to allow placing the public keys on Google's side in the user configuration. That would be a heck of a lot better than just dropping users into never never land." Apparently, "valid" now means "paid someone Google approves to sign the certificate." It's not like commercial CAs have the best security track record either.

34 of 299 comments (clear)

  1. Communications Breakdown by Frosty+Piss · · Score: 5, Insightful

    In a move not communicated to its users before hand

    In a move not communicated to you. I have a Google Apps account and received an email about this a few weeks ago.

    Not good for the small folks.

    A cert from BigNameInternetCompany costs next to nothing (although it might just be worth that much as well).

    My guess is that this is mostly driven by the desire to minimize SPAM email servers using the Google network to abuse their victims.

    One suggestion was to allow placing the public keys on Google's side in the user configuration. That would be a heck of a lot better than just dropping users into never never land.

    Again, a cert that is acceptable to Google is so dirt cheap as to be inconsequential to anyone running a server that needs one. So, the only reason can be that those that object are the crusty RMS types â" everything must be free. Google is more concerned with the health of their network, not random non-paying non-customerâ(TM)s not really needy needs.

    I know that sounds harsh, but Google is not a social services agency.

    --
    If you want news from today, you have to come back tomorrow.
    1. Re:Communications Breakdown by morcego · · Score: 4, Insightful

      My guess is that this is mostly driven by the desire to minimize SPAM email servers using the Google network to abuse their victims.

      Ok, hold on a moment. What does POP3 access over SSL has to do with spam ?

      --
      morcego
    2. Re:Communications Breakdown by js33 · · Score: 3, Interesting

      A cert from BigNameInternetCompany costs next to nothing

      In fact it costs nothing from StartSSL, like several commenters have pointed out, but people forget that the commercial x.509 PKI is for convenience, not security.

      A self-signed cert is highly secure as long as you can verify through independent means that it is in fact the same cert installed on your server, and as long as the private key has not been compromised. In fact this is really the only way you can really get this level of security from even a commercial cert --- to verify independently that it is in fact the cert you think it is, and you have not been subject to a man-in-the-middle-attack.

      It's not as though Google previously made any effort to verify the authenticity of those self-signed certs, or if accepting those self-signed certs as they did before would give their users anything but a false sense of security. Surely it is not a money issue for the "small guy". Commercial certs can be had, if not free from the one provider I already mentioned, for a very minimal price from many different providers, on the order of what the "small guy" is already paying for his domain registration. Why is it that the "small guy" always seems to choose the most expensive, heavily advertised vendors of some service or product and then proceed to complain about the price?

      I have to agree (mostly) with Frosty here. No, the mainstream commercial PKI is not the most highly secure thing in the world, but you're trying to authenticate your server to a big commercial company---you need a commercial cert. And if you're trusting such a big commercial company as Google, then you may as well trust the whole commercial PKI, because you're extending your trust far and wide in either case, which there is nothing wrong with, as long as you be mindful of what you are entrusting to the "big boys."

    3. Re:Communications Breakdown by X.25 · · Score: 3, Insightful

      Again, a cert that is acceptable to Google is so dirt cheap as to be inconsequential to anyone running a server that needs one. So, the only reason can be that those that object are the crusty RMS types Ã" everything must be free. Google is more concerned with the health of their network, not random non-paying non-customerÃ(TM)s not really needy needs.

      Please, explain us how self-signed certs impact the health of their network.

      All ears.

  2. Cue the self-signed-certs are insecure responses. by Rich0 · · Score: 5, Insightful

    I know this will get 400 replies about how self-signed certificates don't provide complete security.

    I'd buy that argument if Google configured their servers to only accept connections over SSL with trusted certificates, and then refused to connect at all otherwise.

    However, they're still allowing unencrypted connections as well. There isn't a single attack you can mount on an SSL connection with a self-signed certificate that you can't also mount on an unencrypted connection.

    Trusted vs untrusted SSL is a false dichotomy - it neglects the most commonly used option of not using SSL at all, which is completely insecure.

  3. Google should then provide signed certs by IBitOBear · · Score: 3, Insightful

    This cut at free flow of information, and this alligation that the cost is trivial in the parent poster's post, suggests that if it were such a nothing then google should offer a means to comply wihtout forcing people to go out and pay a third party.

    If it's so cheap and such a nothing, then what's the problem wiht them providing what is needed to interract with their own service?

    --
    Innocent people shouldn't be forced to pay for inferior software development.
    --"Code Complete" Microsoft Press
    1. Re:Google should then provide signed certs by Threni · · Score: 3, Insightful

      Google can do what they want. This move improves security. Sometimes you have to force people to wake up so that they move their feet out of the fire.

    2. Re:Google should then provide signed certs by spcebar · · Score: 3, Insightful

      Agreed. The problem is not the levity of the price, but the existence of the price itself.

      --
      Which one is the 'anykey'?
    3. Re:Google should then provide signed certs by PlusFiveTroll · · Score: 4, Interesting

      Will it work with STARTSSL free personal certs?

      http://www.startssl.com/?app=1

    4. Re:Google should then provide signed certs by hobarrera · · Score: 4, Informative

      You're right, they're not cheap. Actually they're free.

    5. Re:Google should then provide signed certs by icebike · · Score: 3, Insightful

      This move improves security.

      How does it do that?

      This change only affects those people who configure Gmail to pop mail off of small company (or personal) Linux box which has a self signed certs so that the traffic is encrypted. It then puts this mail in your Gmail inbox. I fail to see any big security hole here. Who is going to run super secret mail on a self signed certificate?

      The work around is to have the Linux box forward a copy to Gmail. At least they would then be using Googl's cert. I'm not seeing this as that much better for over all security.

      --
      Sig Battery depleted. Reverting to safe mode.
    6. Re:Google should then provide signed certs by msauve · · Score: 3, Interesting
      "This move improves security."

      No, it doesn't. According to Google:

      you can disable using SSL in Gmail by unchecking 'Always use a secure connection (SSL) when retrieving mail on the Accounts and Import tab in your Mail settings. However, this means that your password and email will not be protected while sent over the Internet, so we don't recommend disabling this.

      so, instead of using SSL for it's encryption capabilities (Google is now forcing authentication as a bundle), some users will have to leave the connection wide open. Now, I realize that self-signed certs still leave an opportunity for MITM attacks, but something is better than nothing. Google could have cached self signed certs, and notified the user if they changed, which would have at least made MITM interception apparent. They could have made this level of SSL authentication configurable. They could allow users to upload a private CA cert, or the public side of an SS cert. But they didn't. They just changed to "all or nothing," which will push many users to "nothing."

      That in no way improves security.

      --
      "National Security is the chief cause of national insecurity." - Celine's First Law
    7. Re:Google should then provide signed certs by IVI4573R · · Score: 4, Informative

      Yes. My dovecot server is configured with a Class 1 from STARTSSL and Gmail is happy with it. You just have to remember to use the "Server Certificate Bundle with CRLs" provided by STARTSSL in the ssl_ca option so that the chain to CA is complete.

      --
      https://www.accountkiller.com/removal-requested
    8. Re:Google should then provide signed certs by msauve · · Score: 4, Insightful

      "you should really get a recognised SSL certificate if you want to offer SSL protected services, otherwise you're only getting half the benefit of SSL connections - you get encryption but not authentication."

      No, it's perfectly reasonable to run your own CA, as an individual or an organization, distribute your CA cert to those using the service, and go merrily on your encrypted and authenticated way.

      Except for Google, who provides no mechanism to associate a private CA cert, or the public side of a self signed one, with a gmail account.

      --
      "National Security is the chief cause of national insecurity." - Celine's First Law
    9. Re:Google should then provide signed certs by PhunkySchtuff · · Score: 3, Interesting

      No, it's perfectly reasonable to run your own CA, as an individual or an organization, distribute your CA cert to those using the service, and go merrily on your encrypted and authenticated way.

      For $30 per year to get a real cert (or even less, a little googling will quickly product things like 80% off at GoDaddy etc), your time has to be of quite a low value if it's easier/cheaper to run your own CA and distribute certificates (unless, of course, you're doing it all for the fun of it)

      Where self-signed certs are no good is when you need to access your SSL protected service from someone else's machine, or a machine you've not used to access the service from before, and you have to take it on blind faith (or remember a long and complicated fingerprint) that the cert you're getting is the correct one.

    10. Re:Google should then provide signed certs by msauve · · Score: 3, Insightful

      "your time has to be of quite a low value if it's easier/cheaper to run your own CA and distribute certificates"

      Or, you're a large organization and running your own CA means saving $30 x (large number N) per year. Or, you're aware that getting a "real" cert is no guarantee of security.

      --
      "National Security is the chief cause of national insecurity." - Celine's First Law
    11. Re:Google should then provide signed certs by blueg3 · · Score: 3, Insightful

      instead of using SSL for it's encryption capabilities (Google is now forcing authentication as a bundle)

      Because an encrypted communication using only an IP address for authentication is no encryption at all. Any attacker reasonably capable of intercepting your communications to read them is also capable of undetectably executing a man-in-the-middle attack on the SSL connection.

      This increases security because it encourages people who actually want encrypted POP connections to use an approach that actually provides that rather than using an approach that appears to provide it but doesn't.

      It would be nice to have the ability to upload the signer's cert and use that for verification, though. That enables secure use of self-signed certificates.

    12. Re:Google should then provide signed certs by SteveFoerster · · Score: 4, Funny

      alligation

      Is that like an allegation that hides beneath the surface of the river, biding its time?

      --
      Space game using normal deck of cards: http://BattleCards.org
    13. Re:Google should then provide signed certs by Albanach · · Score: 4, Insightful

      How does it do that?

      Presumably if you trust self-signed certificates, anyone can launch a MITM attack against your server with a self-signed certificate. Google would trust the self-signed certificate as being your own and then relinquish your login credentials when it attempts to retrieve the mail.

      Now the MITM has to at least get a certificate from a trusted source that will have to, at a minimum, perform some sort of domain validation.

      The increase in security may not be huge, but there's certainly some gain in security from this, and well worth the few dollars that a domain authenticated certificate costs.

    14. Re:Google should then provide signed certs by ls671 · · Score: 3, Interesting

      I use STARTTLS so Google servers can use my SMTP server with authentication to relay mail I send from gmail. The idea is that I can post from gmail using my real email address and not my gmail address. Trying to relay mail with my real address directly from gmail servers would cause problems with SPF (Sender Policy Framework). It that case, gmail puts your real address in the Reply-To field and puts your gmail address in the From field so it is obvious for people receiving my emails that I posted from gmail.

      I do not have gmail servers popping mail from any of my servers so I haven't tested it.

      After testing a few minutes ago, I can tell you although that gmail still works with my self-signed certificate when it connects to my SMTP server to relay mail. So, having gmail relay mail through your SMTP server still works with a self-signed cert. In order to enable this functionality, you have to provide gmail with a user name and password to connect to your SMTP server.

      Dec 17 21:33:38 mailserver sm-mta[13455]: STARTTLS=server, relay=mail-qc0-f171.google.com [209.85.216.171], version=TLSv1/SSLv3, verify=FAIL, cipher=RC4-SHA, bits=128/128
      Dec 17 21:33:38 mailserver sm-mta[13455]: AUTH=server, relay=mail-qc0-f171.google.com [209.85.216.171], authid=XXX@XXXX, mech=PLAIN, bits=0
      Dec 17 21:33:39 mailserver sm-mta[13455]: qBI2XaZT013455: from=XXXX@XXXX, size=2286, class=0, nrcpts=1, msgid=CAHEH8eWJ121WWK9o87V8SSttDhRHTHZa2NgiygugupZ0ROd3gQ@mail.gmail.com, proto=ESMTP, daemon=MTA, relay=mail-qc0-f171.google.com [209.85.216.171]

      --
      Everything I write is lies, read between the lines.
    15. Re:Google should then provide signed certs by BitZtream · · Score: 3, Insightful

      You may argue, and more qualified than you may argue, but that doesn't mean they are qualified. A self signed cert is useless other than testing. Anyone can walk right through it.

      You would argue it because you don't understand that snake oil doesn't actually accomplish anything other than fooling fools into believing they are secure when they aren't. Thats worse than making people aware of the fact that they aren't secure, in which case they can consider their behavior and curtail it appropriately.

      --
      Persistent Volume manager for Kubernetes - https://github.com/dwimsey/openshift-pvmanager
    16. Re:Google should then provide signed certs by Score+Whore · · Score: 4, Funny

      You've now posted several times that self signed certs are useless and provide no security, in fact they lower security (from what baseline I must ask?)

      So I would make a little bet with you. I will put up $100,000, my testicles in a jar with a small plaque saying "These balls once belonged to a fool." You will put up $10,000 plus any required travel expenses to carry out the wager. The terms of the wager are that I will provide a client and a server system. The server will have a self signed certificate. You will provide the networking equipment of your choice as well as any device(s) you so desire to place in between my client and server. I will make an SSL connection from my client to my server. Your job is to MITM the connection without my being able to detect said MITMing. Note that I am allowing you to build the entire network connecting my two devices, only requirement being that it be standard ethernet. Additionally you do not get to tamper with my equipment, this is about the security of self signed certificates, not whether you can literally or metaphorically crowbar open my systems and install a keylogger to capture the passphrase of my private SSL keys.

      How about it? You game? I can always use an extra $10,000.

  4. Since you need FCRDNS to send mail these days by Vekseid · · Score: 5, Informative

    That means you have to control at least one IP address.

    It's also really hard to send e-mail without at least one domain of your own.

    Reseller pricing of low-end certificates is about the same cost as a domain. From Namecheap and elsewhere.

    That said, I didn't know about this, and forgot to set up SSL at one of my domains. I didn't much care, but my reaction to this is pretty much "Oh, so that's what Google is bitching about. Okay."

    This is much ado about rather little.

  5. Free service gets changed? by Nyder · · Score: 3, Insightful

    You get what you pay for.

    --
    Be seeing you...
  6. Re:Cue the self-signed-certs are insecure response by Burning1 · · Score: 4, Insightful

    This misses the point that trusting self signed certificates significantly reduces the security of CA signed certificates.

    In order to protect against Man in the Middle and other identity based attacks, Google needs a way of certifying that the remote machine is who they say they are. If the service trusts an self-signed certificate, there's nothing preventing a 3rd party from performing a MITM attack by intercepting your traffic and re-signing it with their own key. The only workaround would be to use a known_hosts based system, similar to SSH. This however increases the costs of administration, and still provides avenues of attack.

    I generally agree with Google's move. I think it's a bad thing to compromise the security of CA certs in order to support self-signed certs.

  7. Re:Google can do what they want. by ThatFunkyMunki · · Score: 5, Informative

    Yes, you can. The only issue is that when you are using the gmail interface to download mail from an external POP3 server, if you want the connection to be encrypted, your SSL certificate cannot be self-signed. This does not affect anything to do with using regular gmail with a regular POP3 client.

    --
    If patriotism is racist, is racism patriotic?
  8. Re:Google can do what they want. by PhunkySchtuff · · Score: 4, Informative

    From my reading of the linked article, this has nothing whatsoever to do with fetching your email from Google over POP3 (or POP3S)

    What this affects is if you are running a mailserver that uses a self-signed certificate, or if you're using another email account on a mailserver that uses a self-signed certificate, then you can no longer tell your gmail account to pull the email in from your second account over POP3S, as it can't verify the certificate.

    You can still have gmail pull in your POP email via the non-secure protocol, or have the mail server administrator pay the $30 or so a year it costs to get a valid certificate signed by a recognissed CA.

    You can still fetch your gmail via POP, using SSL or not, although why anyone would want to use POP if they're given any other option (such as IMAP) is beyond me.

  9. Re:Please Explain by Wingman+5 · · Score: 3, Informative

    This is if you want GMail to query another POP3 server and pull it in to GMail, this allows you to do things like use the GMail Web UI for servers that only support POP3.

  10. You are wrong. by Kludge · · Score: 5, Insightful

    But its better -- for Google and users -- for Google not support self-signed certs than to support them in a way which provides illusory security, which is what Google was doing before it discontinued support for them.

    That is wrong. Here is the hierarchy.
    1. No security (OK)
    2. Encryption (Better)
    3. Encryption and Authentication (Best)
    Saying that 1 is better than 2 is wrong. After Google connects to a server just once and stores the key, all subsequent connections can be encrypted and verified that they are made to the same server. This fear of encryption without authentication is very ignorant.

    1. Re:You are wrong. by dch24 · · Score: 4, Interesting

      Examples of snooping that lack the ability to do a MITM attack:

      1. Listening to an encrypted wifi session, then breaking the encryption offline

      2. Tapping into undersea fiber (the listening party is going to have a hard enough time exfiltrating the snooped bytes; setting up a "take over" command and associated equipment is prohibitive due to both the technical and political risks)

      3. Listening device inside a government facility. China famously does this for example by using a small office-supply firm to get equipment into a US facility somewhere is Asia; the copy machine has a hard drive like any copy machine and there's nothing suspicious about that, right? And then you find the second, and the third, and the fourth hard drive hidden in places you would never look. The data is exfiltrated only when the machine is replaced as part of a regular service contract.
      Need I go on?

  11. Re:Self-signed certs have bad cost:benefit for Goo by WaffleMonster · · Score: 4, Informative

    Self-signed certs don't provide any security advantage in the Gmail use case over no SSL

    There is an important difference in the use of SSL provides protection against passive easedropping where an attacker may only be able to listen to but not alter the contents of transmitted data.

  12. Self-signed vulnerabilities by AaronLS · · Score: 3, Insightful

    I like self-signed certs because they are away to leverage SSL support for encrypted connections, but they are vulnerable to man-in-the-middle attacks. Hence the suggested workaround of providing the public key in the Google account so that Google can prevent man-in-the-middle attacks. IMO that is a reasonable suggestion, but many tools for creating self signed certs don't give you an easy way to separate the public key without opening the file and being knowledgeable of it's format. It would be a feature used by probably a tiny percentage of users, and be a point of what-the-heck-is-that-option for the rest. The lack of user understanding would also be a vulnerability, where people might be duped into providing a different public key with malicious origins.

    This has nothing to do with the inflammatory "valid" vs. "paid" statement. There are CAs that provide free certificates, and thus are not vulnerable to man-in-middle-attacks because of the verifiable chain. So they are indeed valid in a sense that there is the trust chain, yet not paid, making the summary's inflammatory statement INVALID. No one is trying to claim self signed certs are invalid, they just leave users vulnerable.

    The last statement about CA's being compromised is somewhat irrelevant to the subject at hand. They seem to be trying to make the point of Google unfairly favoring CA signed certs over self signed certs. So they either feel that Google should also do away with CA signed cert support, or not do away with self signed certs on the basis that CA signed certs are no more secure(as a result of CA's being compromised). I will address both of these possibilities.

    1) Doing away with self signed certs prevents vulnerabilities that most users are probably unaware exist. Thus avoiding more shenanigans like Chinese activists getting arrested when the government snoops their communications using man-in-the-middle attacks. So this is definitely a step in the right direction(although perhaps alternatively could have supported providing public keys out of channel as summary suggests).

    2) Doing away with support for CA signed certs to close the potential vulnerability of relatively rare forged certs? That's like throwing the baby out with the bath water. The system in place significantly improves security for the vast majority of connections. It allows certs to be revoked when found to be forged, and provides a secure connection that cannot be snooped(with the exception of the tiny fraction of invalid certs, which that get revoked anyhow). Self signed certs cannot offer either of these features transparently(without requiring users to setup public keys).

    Self-signed certs can be "forged" in the sense that a man-in-the-middle can present a completely different cert. as the original, and there is no third party verification that would allow that cert to be revoked. Even if it were revoked("hey bob, just calling to tell you to look at the cert on that connection when you get your email and if the key read f0a135... then disconnect" I kid, I kid), the malicious snooper would just create a new self-signed cert for another man-in-the-middle the next time a connection is initiated. For those same reasons, connections made with self-signed certs have very little guarantee of security.

    Usually I'm not concerned about man-in-the-middle attacks, since if someone has gained that level of access to the network I'm connecting over, then things are looking bad already. In places like China though, where the people who control the network are the people who want to snoop on you, it is a ever present danger.

    If there were more user friendly systems in place for managing/retrieving public keys, then self signed certs would be great. Even when I know a cert. is valid, some make it very hard to permanently add the public key as trusted, and thus prompt me with an extra step every time I restart my browser and try to access a page using one.

  13. Re:Cue the self-signed-certs are insecure response by AaronLS · · Score: 5, Insightful

    It is a big deal for a CA to be compromised, I agree on that. However, to use that to then say signed certs are completely useless is not just an exaggeration, it is completely wrong and inaccurate. You sir, are an alarmist

    You threw the baby out with the bathwater... oh the horror. Someone go get the baby back.

    The incidents you describe did not compromise the vast majority of SSL connections. Only a tiny fraction, and only for a limited time span, since the beauty of the CA system is they are able to revoke cert's once discovered to be invalid. Although that can take some time to trickle down since many OS's cache the CA's public key, and is only changed via a system update.

    Self signed certs are far more insecure. At least with CA certs you have a 99.9%+ chance of having a secure connection. With self signed certs, you have 0% guarantee unless you've been communicating public keys out of channel.

    I'm not sure what "job" you are referring to is more difficult. There is a vast wealth of libraries and applications that support SSL, making any "job" involving supporting SSL easy. If that is difficult for you, maybe you should get a different job.

    If you want to take the lead on implementing a new system that provides the same level of security then be my guest. Otherwise all I hear is a bunch of CA bashing non-sense that has no root in statistics.

     

  14. Re:Self-signed certs have bad cost:benefit for Goo by Binestar · · Score: 4, Informative

    Sorry, but it isn't. MITM means the man in the middle pretends to be the server when you talk to him, then pretends to be you when the server talks to him. He then stands in the middle, encrypting to you, encrypting to the server, pretending to be both.

    Check out this video for the video that finally caused me to "get" it. https://www.youtube.com/watch?v=3QnD2c4Xovk

    --
    Do you Gentoo!?