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Encrypt and Sign Gmail messages with FireGPG 206

Posted by CmdrTaco
from the can-you-spot-the-secret-message-in-this-dept-line dept.
Linux.com (Same owners as Slashdot) has a story up about FireGPG and says "Gmail may be an excellent Web-based email application, but there is no easy way to use it with privacy tools like GnuPG. The FireGPG extension for Firefox is designed to solve this problem. It integrates nicely into Gmail's interface and allows you...
Encrypt and sign Gmail messages with FireGPG
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Encrypt and Sign Gmail messages with FireGPG

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  • by Ian McBeth (862517) on Monday June 04, 2007 @10:31AM (#19382535) Homepage
    For me, I just like to use it, to make people think I am doing something.
    Keeps the snoops on their toes.
    • For me, I just like to use it, to make people think I am doing something. Keeps the snoops on their toes.

      I keep them on their toes by acting completely normal, having them looking for steganography.

      • Well, have you found the hidden message in the parent post yet?
        • by u8i9o0 (1057154) on Monday June 04, 2007 @01:08PM (#19384729)

          I keep them on their toes by acting completely normal, having them looking for steganography.
          Well, have you found the hidden message in the parent post yet?
          Sorry, there is no hidden message.
          1. You noted that you use encryption when acting normal.
          2. However, you were posting on /. which has been established (quite conclusively) as abnormal behavior.
          3. Since you were not "acting completely normal", it is obvious that you were not employing any encryption scheme.
          4. :)
          5. Profit!
        • Re: (Score:3, Funny)

          by clem (5683)
          How about a hint -- does it have anything to do with that strange illegible text in your sig?
      • Re: (Score:3, Interesting)

        by UbuntuDupe (970646)
        Actually, I heard that one old prank was to send postcards back and forth between major cities with simple, but cryptic sounding statements. For example:

        "The birds rise at sundown. Where are the minnows?"
        "All is well, north of the river."

        Supposedly, the government would see them and get suspicious, thinking they were coded messages.

        I've also wondered: why doesn't someone test whether the government is reading emails? For example, have some guys plot an imaginary terrorist attack via unencrypted email and
        • by canajin56 (660655) on Monday June 04, 2007 @01:18PM (#19384863)
          Here is why you don't do that: Because why wouldn't a terrorist leave corroborating evidence lying around proving it was all just a test to psych the government out, so they can be let go? While they are interviewing your "third parties" you are being beaten half to death, electrocuted, water boarded, and raped. IF, and its a huge, colossally massive if, they ever EVER believe you that you were just kidding about bombing NY with a dirty bomb, they will testify that you cannot be released since after your brutal torture you probably are now a terrorist even through you weren't before. Plus you can't exactly be let go since the torture techniques are classified information and you might leak them. Just like Jose Padilla. First he HAD a dirty bomb, then he was building one, then he was thinking about it, then he knew somebody who was thinking about it, then nothing...but they have ruled he can NEVER face trial, and can NEVER be released. Their reasoning is their "interrogation techniques" have irreversibly damaged him mentally, so he's too unstable to stand trial. But these "interrogation techniques" are highly classified matters of national security, so he can never ever be allowed to talk to anybody in case he tells them what they did to him (especially not a lawyer). And that would be you. Now remember, he _WAS_ a citizen, and there was no evidence against him. Still tortured and given a life sentence without the possibility of a trial. What fucking chance do you think you have if there IS evidence against you? Well you might have white skin so you just may have some kind of chance.
    • by jimstapleton (999106) on Monday June 04, 2007 @11:04AM (#19383039) Journal
      I only use one-time use pads when sending my emails. It keeps them busy and unable to decrypt the emails!
  • And for the chat (Score:5, Informative)

    by DrYak (748999) on Monday June 04, 2007 @10:31AM (#19382541) Homepage
    And if want PGP encryption for chat (Gmail's associated GTalk or any other protocol like MSN, etc.) there is Pidgin [slashdot.org] (formely Gaim) with plugins :
    • Etiher Pidgin Encrypt [sourceforge.net] (formely Gaim Encryption)
    • Or OTR [cypherpunks.ca]


    • by stinerman (812158) <nathan.stineNO@SPAMgmail.com> on Monday June 04, 2007 @10:36AM (#19382601) Homepage
      Note that OTR is "better". From the OTR site:

      How is this different from the gaim-encryption plugin?
              The gaim-encryption plugin provides encryption and authentication, but not deniability or perfect forward secrecy. If an attacker or a virus gets access to your machine, all of your past gaim-encryption conversations are retroactively compromised. Further, since all of the messages are digitally signed, there is difficult-to-deny proof that you said what you did: not what we want for a supposedly private conversation!
    • OTR is miles better than the gaim-encryption/pidgin-encrypt. Honestly, I don't understand why they won't just kill it and move to OTR for good; it's a fundamentally better security model for something transient like instant messages.

      Particularly since having two mutually-incompatible encryption packages is a pretty crummy state of affairs; it just means that the few users who do use encryption, are going to be fragmented between incompatible systems.

      OTR probably has the greatest market penetration of any IM-encryption system, outside of corporate clients (Sametime, I think, uses encryption by default, although I don't think it's end-to-end, only client-server, because there they want the ability to intercept on the server), because it's built into the fairly popular OS X Adium [adiumx.com] client. So there's already quite a few users out there who have software that supports it. If only some of the other IM clients would start building it in by default, rather than making it an optional addon, I think it would quickly gain traction as a de facto standard. (And that would be a good thing, since it's a good system and open source.)
      • Re: (Score:3, Insightful)

        Particularly since having two mutually-incompatible encryption packages is a pretty crummy state of affairs; it just means that the few users who do use encryption, are going to be fragmented between incompatible systems.

        This is what standards are for. We need a standard for IM encryption, possibly as part of a larger encryption framework. I have no problem advocating a standard, which I think is a lot better idea than advocating a given program/library.

        If only some of the other IM clients would start building it in by default, rather than making it an optional addon, I think it would quickly gain traction as a de facto standard.

        OTR is licensed as GPL/LGPL. As such, I'm not sure a lot of major software makers will be all that keen about implementing it. Take a look at iChat or Yahoo Messenger. They're not going to open source their application just to add an encryption format that is still pret

        • by Alphager (957739)

          OTR is licensed as GPL/LGPL. As such, I'm not sure a lot of major software makers will be all that keen about implementing it. Take a look at iChat or Yahoo Messenger. They're not going to open source their application just to add an encryption format that is still pretty rare and where there is not a lot of demand.

          Which is why they use the LGPL, which allows usage without forcing openness.
          • Which is why they use the LGPL, which allows usage without forcing openness.

            I'm familiar with the LGPL license, but while it is great for "tivoization" type uses, it is usually a no-no for software inclusion. Most corporate lawyers I know don't want employees including LGPL code in distributed software, because the cost of making sure it is compliant and making sure the developers understand what they do and don't have to resubmit, and the cost of documenting the linkages, is too onerous, especially for this small of a chunk of code. It is easier to simply write their own code th

            • by drinkypoo (153816)

              Most corporate lawyers I know don't want employees including LGPL code in distributed software, because the cost of making sure it is compliant and making sure the developers understand what they do and don't have to resubmit, and the cost of documenting the linkages, is too onerous, especially for this small of a chunk of code.

              Is it really this hard to just keep all of the LGPL code in its own files, and only add code to them that needs to be there?

              • Is it really this hard to just keep all of the LGPL code in its own files, and only add code to them that needs to be there?

                For a lot of companies, I think so. We manage a fair number of LGPL and GPL software packages here. Then again, we ship servers preloaded with it, just like Tivo does. The LGPL requires not only changes to the LGPL library, but also all the linkable object files used to glue it to your code base. This means you have to track it all and educate users. Here, most of the developers have a good handle on OSS licensing and we already have to track GPL software we also include on our boxes, making it not a huge

  • by kentmartin (244833) on Monday June 04, 2007 @10:35AM (#19382595) Homepage
    I thought their business model worked on the idea that they could datamine all your email and (among other things) offer you targeted email based on the content therein... this'll screw with that idea...

    "BUY jjhHDJEy6786ERLKLXhdfeprERIOUPewoenOIhgshgrgeyrew now for a low price on Ebay.co.uk"
    • Nah, they'll just start sending 'Soldier of Fortune Magazine'-type ads at you.

    • by blueZhift (652272)
      Interesting question, because datamining email to target ads is exactly what Google said they wanted to do when gmail got started. Since encrypted mail would make this impossible, I wonder if they'll take actions to stop the use of encryption tools with gmail. On the other hand, as it stands, unless they offer such tools themselves, I don't see most users encrypting their gmail anytime soon. So the losses may be acceptable to Google.
  • by LiquidCoooled (634315) on Monday June 04, 2007 @10:36AM (#19382605) Homepage Journal
    -----BEGIN PGP MESSAGE-----
    Version: GNUPG v0.4.0 (GNU/Linux)
    Comment: Wonderful
    ewurnfi3u834j9few4jf9oewfqvi7y&H*&HAwr8hw78er7hfw8 f7hh4839h47f7e
    wf8943f89jw3r8j9fesajaejro5gvl;rhyklyfp[ult0h43jg8 394g84953jgf84
    fnw98efj89324rtuerjgeiorgtjerilgtjireogniregunreng erniguiregt980
    werj
    -----END PGP MESSAGE-----

    I have nothing more to add
  • I thought, their ability to automatically parse the messages — so as to show users the relevant advertisements, was the reason, I am getting an unlimited mailbox with nice interface for free.

    If all/most of my messages are encrypted, how will they know, what to peddle to me? Can't do much on Subjects alone... Or can they?

    • by $RANDOMLUSER (804576) on Monday June 04, 2007 @10:43AM (#19382709)

      If all/most of my messages are encrypted, how will they know, what to peddle to me?
      Aluminum foil. Survival equipment. Wellbutrin.
      • Re: (Score:2, Funny)

        by Anonymous Coward
        Aluminum foil.

        You need tin foil to make the hats - mind control rays pass right through aluminum!!! Don't you ever wonder why everyone still talks about "tin foil" even though all you can buy on store shelves nowadays is aluminum? It's because They don't want you to notice the switch!!!

        Survival equipment.

        Sure, if you want a compass that's got the New World Order's tracking devices already installed. I make my own survival equipment.

        Wellbutrin.

        You see how well my encryption has kept me under your radar?
    • I read all my gmail accounts using POP/SMTP in a real mail program, so I don't see any advertising anyway. Won't make a difference. Except if they try to figure out trends by actually keeping statistics on the content of e-mails going through their system.
      Hmm, maybe that's the reason I need to start using encryption.
      That, and to annoy the NSA of course. /RS 'M-x spook'

  • by RubberChainsaw (669667) on Monday June 04, 2007 @10:43AM (#19382701)
    This extension seems very cool, and I plan to try it out when I get home. When I first read the summary I thought to myself, "A firefox extension and gmail, how much simpler could it get!" But, unfortunately this is not point & click encryption. It requires an additional external program (GnuPG) to function. Even this small, relatively trivial step is too much for beginning to average computer users. Encrypted email is great and all, but I can only send it to other people with encryption-enabled email clients.

    Where is the it-just-works email encrytion for dummies?

    • Re: (Score:3, Funny)

      by LiquidCoooled (634315)
      When I want to totally encrypt an email I just plug in my DVORAK keyboard, put on a blindfold and type as usual.
    • Where is the it-just-works email encrytion for dummies?

      I don't know, but it seems really ... odd to me that:

      1) Geeks really want such encryption to take off.
      2) It shouldn't be that hard to implement.
      3) Governments really, really, really don't want this to happen. (i.e. that everyone can efforlessly encrypt this well)

      Is 3) or 1) working against 2)?
    • Where is the it-just-works email encrytion for dummies?

      AFAICT, it doesn't exist. At least not outside of corporate environments. There are lots of companies that have their encryption set up so that it's transparent to non-technical employees, but it's a lot of work for the people who actually make it run. Lotus Notes, for instance, will do public-key cryptography, using company-wide keyservers -- although it's a proprietary algorithm, or was last time I checked. Once you have the infrastructure in place, the users don't have to think much about it, besides clicking 'encrypt and sign' on the emails they want secured.

      I've also heard that within Apple, they use Apple Mail with S/MIME to great effect ... but if you're just a regular user, getting that feature working is a real PITA. (Though admittedly, most of the trouble is because of the certificate authorities.)

      I think the problem with the free encryption tools is that they're still very much a 'hacker's product,' being designed by fairly advanced users, for other advanced users -- or at least, for users who don't have a problem installing extra software in order to communicate securely. This, IMO, is a mistake; in order for an encryption system to be useful, it has to be widely used. And that means getting it into the hands of people who might not even think, in advance, that they want it. There are lots of people who aren't going to go out and download/install encryption software, but if the feature was there, and working, all the time, they'd probably find themselves clicking the 'Encrypt' button quite a bit.

      There's no real reason why encryption can't be built in. It's just that it tends to get viewed as a peripheral, rather than core, feature, in everything except some corporate packages. However, I think that if it was incorporated more widely, it would quickly become a core feature; but getting over that 'chicken and egg' hump is hard.
      • by TheLink (130905)
        The last I heard, the US Gov will have access to X bits of the Lotus Notes keys (some of the keys bits are taken and encrypted to the US Gov key), so that they get a significant help to cracking stuff if they need to. Something like it's 40bit crypto for the US Gov, and 64 bit crypto for everyone else (other than the intended recipients).
      • Re: (Score:3, Insightful)

        by AeroIllini (726211)
        It's not just that not all commonly used products include encryption, it's that there's no standard infrastructure for key exchange.

        In a standard GPG encryption scheme, each user creates a private key and a public key. Anyone who wishes to send them a message must request their public key in order to do the encryption, and then the private key is used to do the decryption. (Sometimes to save computation time the message is actually encrypted with a symmetrical key, and then the key--which is shorter than th
    • Encrypted email is great and all, but I can only send it to other people with encryption-enabled email clients.

      Where is the it-just-works email encrytion for dummies?

      Well, there's one problem. You'd have to have a consistent standard.

      Also, how would you handle key exchange? For "it-just-works", you'd likely not even ask the user if they want to get a particular senders public key, which makes a man in the middle attack very feasable ( because no one has ever spoofed email headers... ).

      Where would one get

    • by metamatic (202216)

      Where is the it-just-works email encrytion for dummies?

      S/MIME, which is built in to Thunderbird, Apple Mail, Outlook, and every other major e-mail client. You just need to get yourself a certificate and install it.

      http://www.dartmouth.edu/~pkilab/pages/Using_SMIME _e-mail.html [dartmouth.edu]
    • by ThosLives (686517)

      Where is the it-just-works email encrytion for dummies?

      I think it's the same as all true forms of message validation: delivery in person.

      * grin *

  • in my travels i can across this javascript-based RSA cryptography demo [stanford.edu]. if you want to use it, hit Generate, then send the first two numbers (Modulus and Public Exponent) to whoever you want to talk to. they have to do the same. you enter their modulus and exponent into another window to encrypt.

    the code is BSD-licensed. i've been meaning to write a larger javascript app to hold your keys and everyone elses' in a single window, and with a click of a button create a block of XML that you can copy+paste t
  • You know you can use POP and SMTP with Gmail? GPG and S/MIME work just fine as far as I've found.

     
  • by emj (15659) on Monday June 04, 2007 @10:48AM (#19382819) Homepage Journal
    I've been using the S/MIME plugin for Firefox [jones.name]. and it's great. I'm not sure I like the way you have to apply for a certificate from Thawte, but it works and it's very painless.

    This is not painless and easy, and IMHO S/MIME is alot nicer implemented than PGP signatures.
    • Re: (Score:3, Interesting)

      by Kadin2048 (468275) *
      This is not painless and easy, and IMHO S/MIME is alot nicer implemented than PGP signatures.

      S/MIME is oftentimes more slickly implemented, because it tends to get more use on the corporate side, but I think that it's unsuited for wide use because of its reliance on centralized certificate authorities. The whole certificate-based infrastructure isn't anything that most people want to have to deal with.

      For 90% of all communications, what people want is an email (or IM, or whatever) version of PGPfone -- they
      • One thing that is CERTAINLY true is that most email users have zero interest in maintaining a web of trust. That means PGP is right out.

        S/MIME relies on people trusting third party certificate authorities and acquiring the certificates of other in order to send encrypted messages. This actually COULD work if the major email vendors agree to cooperate on some sort of certificate distribution method, and provide an easy way for people to get keypairs in the first place. This is at least possible.

        Something wit
        • by Fred_A (10934)

          Email encryption will come eventually, but it will probably be in the form of S/MIME and be pushed by the likes of Google and Yahoo. There is no other way that is even remotely feasible.
          Sad but most likely true.
        • by Kadin2048 (468275) *
          One thing that is CERTAINLY true is that most email users have zero interest in maintaining a web of trust. That means PGP is right out.

          You don't really need the web of trust for PGP. You can use it without any of that quite easily. You grab the keys from a keyserver, and then if you're paranoid or worried about MITM attacks, you verify the fingerprint with the recipient through a side-channel (voice phone, whatever). It's just like PGPfone.

          Unfortunately, PGP and the 'web of trust' are often conflated, but
          • you verify the fingerprint with the recipient through a side-channel
            F A I L .
             
            There is just no way that could reach widespread adoption. Only a PKI model, backed by major mail providers, could have a chance. My mom will never understand fingerprinting. She could understand "This message is signed by John Doe!*" showing up in her mail client, where the asterisk means, "according to Verisign, who is trusted by Gmail."
    • by emj (15659)
      Perhaps I should explain abit more, the GPG plugin has problems with GMail wordwrap, and correctly verifying signatures of emails received by gmail.

      But it works wonderfully to sign short messages, but nothing more complicated.

      It took quite sometime for the S/MIME extension to mature enough to be usable, so this may work in a couple of months..
    • by gad_zuki! (70830)
      s/mime is great and simple. This is what geeks should be pushing onto their friends not gpg. Most mail clients support it. The worst of it is that you need to make a cert. That requires some hand holding, but it sure beats endless hand-holding with gpg or old pgp installs.
    • Does that plugin actually support signatures yet? Encryption is great and all, but has way less useful security properties without signatures.

  • Only Gmail? (Score:3, Interesting)

    by Rob T Firefly (844560) on Monday June 04, 2007 @10:51AM (#19382853) Homepage Journal
    While the site says only Gmail is supported, could this be made to work with other web apps? It'd be neat to have something like this for webmail on my own domains, forum-based messages, and so on.
  • by croddy (659025) on Monday June 04, 2007 @10:53AM (#19382877)
    This works with any textarea, by the way, not just GMail. Not sure why the summary doesn't mention that.

    -----BEGIN PGP SIGNED MESSAGE-----
    Hash: SHA1

    This works with any textarea, by the way, not just GMail. Not sure why the summary doesn't mention that.
    -----BEGIN PGP SIGNATURE-----
    Version: GnuPG v1.4.6 (GNU/Linux)
    Comment: http://firegpg.tuxfamily.org/

    iD8DBQFGZDU/WCKEX KsCq6IRAvAtAJ96BAdus/rVCXS+NxlEbMsDdNxTCgCfe+da
    T yi/KWbgNLQUq/qssCj2YR4=
    =Y2mA
    -----END PGP SIGNATURE-----
  • by biftek (145375) on Monday June 04, 2007 @11:09AM (#19383091)
    I haven't used gmail that much, but I was under the impression that it saved drafts of what's in the composition textbox at intervals.

    That data would be all cleartext wouldn't it? Seems a tad risky to me.
    • While you are correct that end-to-end encryption is best, having ISP-to-end encryption is still a million times better than having no encryption at all.
  • I wonder what Adsense will make of this?
  • FireGPG is great, I suppose, but doesn't help those of us who only use GMail via POP3/SMTP, both to avoid advertising and have mail archives under our own direct control.

    In fact, FireGPG actually benefits Google and its advertising goals, since it only functions via Firefox and Google's ad-infested Web interface.
  • by Cheesey (70139) on Monday June 04, 2007 @12:32PM (#19384159)
    I understand that in some countries, you are legally compelled to provide the keys to access files encrypted with PGP, GPG, etc. if the authorities demand access. If you refuse to produce a working key, or claim to be unable to do so, a judge is able to assume that you are deliberately hiding something.

    Firstly, I wondered if anyone could confirm this? I have heard that it is the case for Britain at least, although I don't see how it can possibly be legally compatible with the presumption of innocence.

    Secondly, I wanted to suggest that perhaps this is a reason not to use PGP, because PGP encrypted information can always be decrypted using the recipient's key - even many years after the message was originally sent. So law enforcement officers will be able to get old PGP-encrypted documents from your email account (probably even if you delete them, thanks to backup tapes). They'll then be able to force you to decrypt them, and if you don't, they can assume you are witholding the key because the files are full of terrorist plans or whatever.

    I suggest that people should only use cryptosystems where the session keys are destroyed immediately after use, such as SSH and (possibly) some secure instant messaging services. Even if law enforcement officers use a wiretap to record everything sent by you over an SSH connection, and then seize your computers, they still can't recover the plaintext because the session keys have already been deleted. It's impossible for you, the suspect, to produce the keys, which should help your legal defense. Here's a way to chat securely by SSH [vanemery.com].. if you need to transfer files, you can use SFTP.
    • by aaron.rowe (40518)

      I understand that in some countries, you are legally compelled to provide the keys to access files encrypted with PGP, GPG, etc. if the authorities demand access.

      Yes I believe that is the case in the UK [bbc.co.uk] (I am too lazy to find out if this is actual law now, to be honest I'm a bit confused if it is or not)

      However, I don't have a problem with this. We use GPG encryption for all our corporate emails, some of our staff are working in countries where it is quite likely that somebody at an ISP could be bribed

    • by westlake (615356)
      I have heard that it is the case for Britain at least, although I don't see how it can possibly be legally compatible with the presumption of innocence.

      You don't have to be target of an investigation to be searched, what matters is that relevant evidence may be in your possession.

      In the american system, the presumption of innocence sets a high standard for conviction in a criminal trial - a standard of civility and caution that ought to be maintained through every stage of the criminal process.

      But to obt

    • Perhaps, but that's only one use of PGP/GPG. You can also send entirely non-encrypted messages that have a digital signature from your key to authenticate that the message came from you. You can also use it to get a digital signature of files you're distributing. More secure than MD5 (etc, etc) hashing (in theory, at least, given only you have the private key to generate the signature), should prove that you created and approve the file (so you don't have unscrupulous people attacking your server and hid
    • Re: (Score:2, Informative)

      by m50d (797211)
      Firstly, I wondered if anyone could confirm this? I have heard that it is the case for Britain at least, although I don't see how it can possibly be legally compatible with the presumption of innocence.

      It's not the case; there was a bill proposed which would have done that, but civil rights activists got it altered so they can only compel you to give up your encryption keys if they can proove you have them.

      Secondly, I wanted to suggest that perhaps this is a reason not to use PGP, because PGP encrypted in

      • Thanks, most informative!

        The --show-session-key option looks handy - but in a way, this illustrates the second point I was getting at, which is that information encrypted with GPG can be recovered as long as any recipient can be forced to give up his private key (or run --show-session-key). This is something that any GPG user should bear in mind, particularly as GPG ciphertext will sit in email boxes for many years. You're trusting the recipient to keep his key secret forever: you trust him now and in the f
    • by Sloppy (14984)

      I suggest that people should only use cryptosystems where the session keys are destroyed immediately after use

      For realtime communication (e.g. phones), that makes sense, but when does "after use" happen with email? Whatever your answer, many people will disagree. There's no right time to stop remembering the session key.

  • by tayker (1111273)
    I've been using Freenigma (http://www.freenigma.com) way before I even heard of FireGPG, and they've had a Firefox extension since then too.
  • You would think that adding GPG would be a next logical feature for Google to add...well, anything that will get my mom to use GPG will make me smile.

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