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The Pentagon Says It Will Start Encrypting Soldiers' Emails Next Year (vice.com)

An anonymous reader shares a Motherboard report: Basic decade-old encryption technology is finally coming to Pentagon email servers next year. For years, major online email providers such as Google and Microsoft have used encryption to protect your emails as they travel across the internet. That technology, technically known as STARTTLS, isn't a cutting edge development -- it's been around since 2002. But since that time the Pentagon never implemented it. As a Motherboard investigation revealed in 2015, the lack of encryption potentially left some soldiers' emails open to being intercepted by enemies as they travel across the internet. The US military uses its own internal service, mail.mil, which is hosted on the cloud for 4.5 million users. But now the Defense Information Systems Agency or DISA, the Pentagon's branch that oversees email, says it will finally start using STARTTLS within the year, according to a letter from DISA. DISA's promise comes months after Senator Ron Wyden (D-Oregon) said he was concerned that the agency wasn't taking advantage of "a basic, widely used, easily-enabled cybersecurity technology."

63 comments

  1. Available Encryption by Frosty+Piss · · Score: 4, Informative

    None of this, of course, is to say that encryption of email itself has been un available. Indeed I use the credentials on my CAC (Common Access Card) to encrypt most if not all of my email before sending it.

    --
    If you want news from today, you have to come back tomorrow.
    1. Re:Available Encryption by Anonymous Coward · · Score: 1, Funny

      I was about to be aghast as the article implies there's been "no security"

      Shoulda remembered I was reading a slashdot post...

    2. Re:Available Encryption by Anonymous Coward · · Score: 0

      I expected as much. Furthermore, StartTLS is no panacea, an active MITM peer can simply strip the request. However, it is very simple to deploy and an extra security layer can't make the security worse.

    3. Re:Available Encryption by Anonymous Coward · · Score: 1

      So every single military transaction is prone to human error and or complacency. This isn't a nuanced criticism. It is in fact damning.

    4. Re: Available Encryption by dougdonovan · · Score: 1

      this tells me that the pentagon could care less about the security of the u.s. soldiers emails until now, 2017.

    5. Re:Available Encryption by Anonymous Coward · · Score: 1

      The article is full of issues. #1, the MAIL.MIL system is what they are talking about and the connections it makes with "external" MTA's.
      Internally, mail has been routed over SSL/STARTTLS connections. The Exchange servers before the DEE migration also used secure relay for messages.

      Mail items themselves have been encrypted using CAC cards and probably one of the largest implemented PKI infrastructures out there. In fact, the DoD PKI/PKE is so large and expensive (cards are $30+ each and routinely get burned/re-issued foolishly) that the DoD-CIO has been looking for an alternative. Some of the alternatives I have seen proposed are even more foolish.

    6. Re:Available Encryption by Anonymous Coward · · Score: 0

      But of course you *don't* use the credential on your CAC to do any such thing. You can use it to *sign* your emails (non-repudiation). Your correspondents could use your public key (iff their mail systems are compatible) to encrypt mail to you, but you need keys for all your recipients to encrypt mail to them -- and that has nothing to do with your CAC and everything to do with the recipients credentials and infrastructure.

    7. Re:Available Encryption by Anonymous Coward · · Score: 0

      > Mail items themselves have been encrypted using CAC cards

      Only when someone chooses to use it. I'd bet maybe 50% of the people with the ability to use this are still clueless how it works. (Based on: the public NEVER uses PGP. Maybe if you are some kind of security expert and have spread your public key around.)

      I'd bet Joe Plumber doesn't even know there's easy to use extensions around like Mailvelope that allow easy as pie usage of PGP with gmail/yahoo/whatever. Because of this one simple reason: It's not available for mobile phones. Might as well be invisible to 99% of the population.

    8. Re:Available Encryption by Frosty+Piss · · Score: 1

      So every single military transaction is prone to human error and or complacency.

      Why? You're making a huge ASS umption that most if not all people who send sensative email are not like me. Of course I work for the Air Force where people are intellegent, but the idea that the DoD is populated by morons is a stereotype prepetuated by people who have never had meaningful interestion with very many people who work for the DoD.

      --
      If you want news from today, you have to come back tomorrow.
    9. Re:Available Encryption by Anonymous Coward · · Score: 0

      intellegent

      'nuff said! ;-)

    10. Re:Available Encryption by CronoCloud · · Score: 1

      Based on: the public NEVER uses PGP. Maybe if you are some kind of security expert and have spread your public key around.

      "I" use PGP, and I am no security expert. My pubkey is available right here on Slashdot at the usual http://slashdot.org/~CronoClou...

      Because of this one simple reason: It's not available for mobile phones. Might as well be invisible to 99% of the population.

      It most certainly is, look for OpenKeychain on Google Play, it integrates well with the K9 Mail app.

    11. Re:Available Encryption by Frosty+Piss · · Score: 2

      'nuff said! ;-)

      Harping on spelling erors is the sign of an unsecure moron...

      --
      If you want news from today, you have to come back tomorrow.
    12. Re:Available Encryption by Anonymous Coward · · Score: 0

      Only when someone chooses to use it. I'd bet maybe 50% of the people with the ability to use this are still clueless how it works. (Based on: the public NEVER uses PGP. Maybe if you are some kind of security expert and have spread your public key around.)

      Encryption and digital signatures are turned on by default, whether using Outlook or OWA as a client.

      Granted, the user can turn those off, but they have to make the choice.

    13. Re: Available Encryption by Anonymous Coward · · Score: 0

      CAC mail is just SMIME. I get it all the time from .mil accounts, and I have my mail agents on macOS and iOS to sign and encrypt by default. SMIME is absurdly convenient.

    14. Re:Available Encryption by peragrin · · Score: 1

      The average person is barely above the level of moron and half of them are dumber than that. I start with the assumption everyone is an idiot and wait until proven wrong on a case by case basis. Yes I include myself in that. While I generally learn from my mistakes after 40 years I still find instances of what was I Thinking when I recently did X.

      It isn't that there are not smart people at the DOD. It is the average is well average. And that doesn't fill me with confidence. I work with smart people. People who have used computers for 20 years. And I still have to explain basic file handling and email concepts to them. it is even more baffling when OCD organized people , people who organize parts and clothes by size color and shape. have 100 files and folders on their "desktop" computer and can never find what they are looking for.

      Look around DOD people don't ask for help as that is not the military way. How many "special case" and special snow flakes do you have to deal with?

      --
      i thought once I was found, but it was only a dream.
    15. Re: Available Encryption by Anonymous Coward · · Score: 0

      They only realized email could be a problem when Hillary started killing soldiers in Bengazi.

    16. Re:Available Encryption by Frosty+Piss · · Score: 1

      It isn't that there are not smart people at the DOD. It is the average is well average. And that doesn't fill me with confidence. I work with smart people. People who have used computers for 20 years. And I still have to explain basic file handling and email concepts to them. it is even more baffling when OCD organized people , people who organize parts and clothes by size color and shape. have 100 files and folders on their "desktop" computer and can never find what they are looking for.

      I understand your point.

      I work exclusively with pilots, most of whom are Academy grads as well as having advanced degrees, mostly science but it varies, from well known schools.

      So my exposure is probably skewed. The "rank and file" actually have to do fairly regular computer security and safety training to maintain network access, but absorbing the essentials is a variable.

      I can not speak for the Army or other DoD departments, only mine, which in general is made up of educated people.

      - Frosty

      --
      If you want news from today, you have to come back tomorrow.
  2. Idiocracy by Anonymous Coward · · Score: 1

    It is here:

    The US military uses its own internal service, mail.mil, which is hosted on the cloud for 4.5 million users

    What could possibly go wrong?

  3. Cloud? What cloud? by magarity · · Score: 1

    "which is hosted on the cloud "

    Ah, yes, "the cloud". Like there is just one. Thanks for the specifics. Does anyone know the details here; is the military really using AWS for email hosting?

    1. Re:Cloud? What cloud? by Anonymous Coward · · Score: 0

      Probably AWS GovCloud or Azure GovCloud.

  4. How email works.... by Anonymous Coward · · Score: 2, Informative

    ...I think people have misconceptions about how exactly emails works. It's not bounced around from server to server until it gets to it's destination.

    It's delivered directly to whichever server(s) your specified in your domain's mx record. So emails cannot simply be intercepted by whomever just like that.

    However by default it is sent as clear text, which means in theory your Tier 3 (your ISP), tier 2 and tier 1 providers could intercept those emails since the packets have to pass through their networking equipment to get to their destination. But if most confidential emails are internal, then you could setup VPN tunnels between servers and that solves that problem.If you are sharing top secret or confidential military info , you should be encrypting every email you send via your email client, regardless if the servers transmit it in clear text or not.

    1. Re:How email works.... by Anonymous Coward · · Score: 2, Informative

      > So emails cannot simply be intercepted by whomever just like that.

      It absolutely can be intercepted by whomever just like that. Just because email doesn't bounce around at the application level doesn't mean packets don't bounce around at the transport level. Do a traceroute between mail servers. Any one of those routers (and any devices in between them that silently pass packets) can be compromised. Any link in between them can be compromised. Don't say it can't happen. The government at least already has their ear in many high tiers, so at least they can listen, if not more large companies. Also, go to a coffee shop and your credentials will be blasted all over the place if you're not careful.

    2. Re:How email works.... by scdeimos · · Score: 1

      If you are sharing top secret or confidential military info , you should be encrypting every email you send via your email client, regardless if the servers transmit it in clear text or not.

      ^ This.

      Nobody should rely on STARTTLS actually working anywhere, any time, especially in countries like Australia where ISPs are legally required to MITM all SMTP connections on behalf of the United States "intelligence" services. ISP do this with proxy appliances that remove the STARTTLS capability from the origin server's greeting and also return "500 Syntax error, command unrecognized" to any STARTTLS requests from clients so that they can continue to capture outbound messages in clear text.

      Usually the quickest way to detect such things is to turn on "Enforce secure connections" in your mail client's SMTP settings, and hope that it honours it. They'll usually reveal themselves when you telnet to mail.google.com:25 (or the like) by including a bunch of asterisks in the origin server's greeting line, "220 ********** service ready."

  5. Um... by hackel · · Score: 1

    They're talking about *personal* emails, right? Surely they aren't *that* incompetent that they're sending official communications over unencrypted email? PLEASE tell me they're not that stupid...

    1. Re:Um... by Anonymous Coward · · Score: 0

      They just announced that it will take them one entire year to change a basic setting on their email servers. So yes, they are that stupid.

    2. Re:Um... by Anonymous Coward · · Score: 0

      You can find many WWI and WWII posters for GIs about watching what you say in mail from the front lines. There was an entire section of military censors to check mail for revealing info. Glad to see the Pentagon circling back around to 1914 for another go.

    3. Re:Um... by jeff4747 · · Score: 3, Informative

      DoD networking isn't quite the same as what's available to the rest of us.

      "Normal" stuff goes over something called NIPRNet. It uses Internet protocols and is connected to the Internet via a few gateways, but if you are emailing from .mil to .mil, it stays on NIPRNet. So it's a bit like emailing another employee at work - The message stays within your employer's network so it's hard(er) to MITM.

      Important things go over SIPRNet, JWICS or another more secure network. Encryption in-transit over those networks has been standard since those networks were built, and is done via hardware devices.

    4. Re:Um... by tie_guy_matt · · Score: 2

      Yes, you should not send official communications unencrypted. But even sending personal information unencrypted may be bad. If one person emails his wife saying that he is stationed at base X then that is no big deal. But if a thousand people say that they just got stationed at base X within a short period of time then that might be bad. There is a reason why during WWII before d-day they officially put Patton in charge of an inflatable and fake army. They were trying to convince Hitler that Patton's attack would be the real d-day and that any attacks before then were just diversions. If they had email back then, and Hitler noticed that none of Patton's troops were actually sending email to their family, then WWII might have had a different outcome.

    5. Re:Um... by AHuxley · · Score: 2

      It would depend on who is talking or emailing. Who, why and how could be of great interest to other nations.
      What could go wrong?
      Someone on a ship sends an email home with the final server been a very average for profit .com in the USA?
      Some faith or cult member or dual citizen makes a copy of all .mil related material as they got work deep in the .com and have total trusted access for work?
      Another nation slowly builds a database of all in use .mil accounts (via some external agency or cover .com or outsourcing partner) and the trusted to/from/content parts.
      Interesting gossip and news might filter out over years given the amount of data collected.
      Only needs one person and their hidden server after getting a trusted job for any big telco. No buddy system in the private sector and all that over time working support issues is a cover.
      The use of social media or internet use?
      Other nations set up psychological warfare accounts to attract the attention of an average mil users online?
      Instead of spies been just off base waiting to turn people in bars and clubs they are now online?
      Spies on base give lists of sites that all the interesting mil people visit, the gossip about lifestyles and people get chatting with new friends.
      The 1950's mil human efforts in a digital world.

      --
      Domestic spying is now "Benign Information Gathering"
    6. Re:Um... by Anonymous Coward · · Score: 0

      mail.mil, which is hosted on the cloud

      Um....

    7. Re:Um... by Anonymous Coward · · Score: 0

      That's a reporter talking. The portal to access that is apparently web.mail.mil, which resolves to 156.112.92.102 for me, and a WHOIS on that shows DISA. So by "on the cloud", they really mean "accessed through a browser"

  6. STARTTLS is mostly useless by Anonymous Coward · · Score: 1

    Most SMTP servers that implement STARTTLS don't even bother to verify the certificate presented to them by the remote host. Pretty trivial to MITM this traffic. This is basically the equivalent of putting a crapton of post cards in a lock box with a skeleton key. It'll keep honest people from reading your mail..thats about it.

    The real solution is to encrypt the CONTENTS of the email using something like S/MIME or GPG.

    1. Re:STARTTLS is mostly useless by Anonymous Coward · · Score: 0

      Spoken like someone who doesn't understand the difference between encryption and authentication.

  7. MITM by DrYak · · Score: 4, Informative

    StartTLS is no panacea, an active MITM peer can simply strip the request.

    Actually, no.
    - if you set to StartTLS to "required" (or if you use IMAPS), your client will only go further if a successful SSL/TLS encrypted link is established with the server.
    The MITM can't just strip the request, the client will refuse to connect.
    - SSL/TLS links will fail if they are not signed by a recognized authority.
    The attacker needs to have a key that is signed by a trusted authority (and thus either needs to have a certificate issuer in cahoots - has actually hapenned with some cert authorities in the past - or needs to manage to get control of the e-mail server (thus can actually access without MITM. OR can steel the original private key and freely MITM. OR can generate a new key and have it at least non-EV signed and use this new key for MITM)

    MITM is the main class of problems that SSL/TLS can succesfully fight (when done right).
    (As opposed to "privacy" class of problems, which are better handled with end-to-end encryption, like PGP / GPG (web of trust) or S/MIME (public key /certificates) )

    --
    "Sufficiently advanced satire is indistinguishable from reality." - [Tips: 1DrYakQDKCQ6y52z6QbnkxHXAocMZJE61o ]
    1. Re: MITM by Anonymous Coward · · Score: 1

      StartTLS cannot be set as mandatory for SMTP connections between servers. There is simply no way to tell the other side that you want StartTLS.

      Client to server can of course be protected

    2. Re: MITM by zlives · · Score: 0

      what!!!!

    3. Re:MITM by Anonymous Coward · · Score: 0

      - SSL/TLS links will fail if they are not signed by a recognized authority.

      I would hazard to guess that 80% (or more) of MTAs use self-signed certs. And even if you don't, most other people probably do, and you can't do verification.

      Unless the major webmail providers say "starting 2019 we're verifying", then no one else is going to do anything.

      I'm all for using STARTTLS to help make the lives of three-letter agencies harder so they just can't 'tap glass', but I'm under no illusions that an active attacker couldn't surveil most organizations.

    4. Re: MITM by RLaager · · Score: 3, Informative

      There actually is a way to tell the other side you want TLS. It's called DANE (RFC 7672). It's new and not widely used yet.

      Here's a presentation on the topic:
      https://www.ietf.org/proceedin...

    5. Re: MITM by silas_moeckel · · Score: 1

      This is done all the time, defined relays can require StartTLS pin keys and a slew of other thigs. It can even be one sided. RFC 7672 makes this more common by allowing it to be automatic.

      --
      No sir I dont like it.
    6. Re: MITM by Anonymous Coward · · Score: 0

      The SMTP protocol between mail servers is the same as the one between mail clients and their local mail server, and definitely supports negation of encryption -- see https://tools.ietf.org/html/rfc3207.

      All the major mail servers allow you to configure TLS as a requirement for successful delivery, both globally or to specific destination domains.

  8. Bring back Lotus Notes! by s.petry · · Score: 1

    Oooooohhhhhmmmmmm

    ps I actually loved Notes specifically because it was so damn secure. Hard and expensive to manage, so the bean counters didn't agree with me.

    --

    -The wise argue that there are few absolutes, the fool argues that there are no probabilities.

    1. Re:Bring back Lotus Notes! by ctilsie242 · · Score: 1

      Notes at least gave everyone their own private key that was used for everything.

      My question is, can S/MIME, or even Symantec's PGP fill in this gap for secure E-mail? Symantec's PGP had the ability to use ADK (additional decryption keys) for recovery, and work pretty well. It would be another add-on to Outlook, but done right, a compromise of a mail server would be mitigated by doing this.

    2. Re:Bring back Lotus Notes! by Enigma2175 · · Score: 1

      Depending on how the PGP server is set up it can also proxy the connection and do the encryption on the server itself, a lot of companies are set up that way. The encryption server sits between the MTA and the mail gateway or the Internet and encrypts/decrypts on the fly so compromising the mail server still would give the attacker access to plaintext messages. Actually encrypting mail is a solved problem, the problem is with key exchange. Despite many attempts at searchable keyservers and different keyserver naming conventions, sharing keys usually requires manual intervention. Unless this problem is solved email encryption will never be widespread.

      --

      Enigma

  9. Email is not being encrypted by Train0987 · · Score: 3, Interesting

    Only the connection between the mail client and the mail server is encrypted. Once it leaves the mail server to go to the recipient it is no longer encrypted.

    1. Re:Email is not being encrypted by Anonymous Coward · · Score: 0

      That is not usually true. Most server to server transmission uses TLS as well. It's been on by default in most MTAs for a decade.

    2. Re:Email is not being encrypted by thegarbz · · Score: 1

      That makes no sense. I suppose you're talking about once it leaves one mail server to go to another mail server it is no longer encrypted. But that scenario is only relevant if you're going to another server you don't control. That is not likely the case here.

    3. Re:Email is not being encrypted by Anonymous Coward · · Score: 1

      It's been on by default in most MTAs for a decade.

      Maybe in univeristies, but not anywhere in the real world. The only times our enterprise mail servers receive TLS (or even STARTTLS) mail is when we're testing it ourselves.

    4. Re:Email is not being encrypted by Train0987 · · Score: 2

      It makes perfect sense. In most use cases the only encryption is between the mail client and its server. When you send an email from your client it goes to your server and then to the recipient's mail server (based on the recipients MX record). With STARTTLS the only "secure" connection is between your mail client and your mail server. Your mail server will almost always then send it out to the recipient on their wire in plain text. That's how email works, and has worked for 50 years. TLS is really just an attempt to put that plain-text horse halfway back in the barn. For those arguing that this doesn't matter because the .MIL address space is already contained between .MIL sender and recipient... well, then finally implementing STARTTLS doesn't matter in the first place. Not every recipient has a .MIL address. If a .MIL send to a .GOV then it's leaving that contained network - in plain text - as it will with any other TLD recipient. Disclosure: I manage a few .GOV domains/mailservers.

    5. Re:Email is not being encrypted by guruevi · · Score: 1

      If you have a properly configured and standards-compatible e-mail server (not Exchange) then every e-mail from at least Gmail should be TLS.

      --
      Custom electronics and digital signage for your business: www.evcircuits.com
    6. Re:Email is not being encrypted by Anonymous Coward · · Score: 0

      Are you from '90?

    7. Re:Email is not being encrypted by Anonymous Coward · · Score: 0

      It is interesting how Exchange became subverted. It was originally written by the Open Group, the guys that hold the UNIX trademark and the protocols were standards compliant. MS in their infinite wisdom, subsequently messed it up in weird and wonderful ways.

  10. Backdoor by XSportSeeker · · Score: 2

    Are they demanding a backdoor to be build on those too?

  11. Next year? by Anonymous Coward · · Score: 0

    We rolled out PKI certs for the Marine Corps back in the early 2000s. Stored on floppy disks, cuz we were ballers like that.

  12. Decades old encryption? by Anonymous Coward · · Score: 0

    They're busy gearing up the manuals and powerpoint for ROT13 training.

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  14. They are going to encrypt? by fox171171 · · Score: 1

    Pedophiles. Think of the children.

  15. How it works in 2017: by thegarbz · · Score: 1

    When you send an email from your client it goes to your server and then to the recipient's mail server

    Your connection to the server is encrypted. If your recipient is on the same server then no further transmission is necessary. If you're recipient is within an internal network who's servers you can control then the further transmission can be encrypted if the admin chooses it to be. Then the only remaining piece is to read the mail using encryption. And that is precisely what is happening in this case.

    Your mail server will almost always then send it out to the recipient on their wire in plain text.

    Get with the times. Email servers these days will "almost always" send out to the recipient using encryption. What does almost always mean? Well according to Google 86% of messages sent on to other servers are encrypted in transit and 88% of messages received from other servers are encrypted in transit. https://www.google.com/transpa...

    But don't take my word for it, open your email and check the headers. You'll be amazed at the number of emails that will bounce between all servers using TLS encryption in transit.

    Technology changes*, you need to change your view with it.
    *1 year ago inbound encryption coverage at Google was around 75%

  16. About Time by Anonymous Coward · · Score: 0

    Does anyone else find it amusing and a little odd that the worlds most technologically sophisticated military super-power doesn't already encrypt their internal mail at all levels?

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