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Do Slashdotters Encrypt Their Email? 601

An anonymous reader writes "Many years ago when I first heard of PGP, I found an add-on that made it fairly simple to use PGP to encrypt my email. Despite the fact that these days most people know that email is a highly insecure means of communication, very few people that I know ever use any form of email encryption despite the fact that it is pretty easy to use. This isn't quite what I would have expected when I first set it up. So, my question to fellow Slashdotters is 'Do you encrypt your email? If not, 'Why not?' and 'Why has email encryption using PGP or something similar not become more commonplace?' The use of cryptography used to be a hot topic once upon a time."
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Do Slashdotters Encrypt Their Email?

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  • No (Score:5, Insightful)

    by Anonymous Coward on Monday December 19, 2011 @11:11PM (#38429792)

    Nor does anyone else. Unfortunate, but true.

    • Re:No (Score:5, Interesting)

      by Anonymous Coward on Monday December 19, 2011 @11:16PM (#38429848)

      I think it's largely pointless anyway...

      Most people (myself included) use a web based email client, where the plain text form of the email would be easily snatchable by the one party with any likely chance to actually intercept an email.

      Cryptographic signing has a place, but even that falls into the cryptogeek fantasy realm, but If you're into that sorta thing.. you can always join the Debian community.

      • Re:No (Score:5, Funny)

        by ZorinLynx ( 31751 ) on Tuesday December 20, 2011 @12:05AM (#38430292) Homepage

        "cryptogeek fantasy realm" indeed. Reminds me of this comic that tells it like it is. []

        • Re:No (Score:5, Insightful)

          by wanzeo ( 1800058 ) on Tuesday December 20, 2011 @03:59AM (#38431704)

          I am tired of seeing this comic used as a dismissal of encryption, it is a joke. If you actually think someone is going to drug you or hit you with a wrench, then you have reached a level of paranoia far more ridiculous than the idea of using 4096 bit encryption.

          I use the very user friendly disk encryption that the Fedora installer provides, and I feel much more at ease taking my laptop out in public.

          As for email, no I don't encrypt them, but I might be willing to learn if the summary had more info than a wikipedia article for PGP.

          • Re:No (Score:5, Insightful)

            by neyla ( 2455118 ) on Tuesday December 20, 2011 @04:43AM (#38431856)

            Indeed. This argument does nothing to diminish the usefulness of crypto.

            Yes people can force you to do various things, but the likeliness of that is lower than the chance that they'll do the same thing secretly if they can get away with it.

            Just because someone can hit you with a wrench and take your card-key, it doesn't follow that locking your house is useless. Just because someone can hit you with a wrench until you give up your PIN-code, it doesn't follow that having the card be pin-protected is useless.

            That something doesn't protect against -all- threaths, doesn't make it useless. It's still useful if it protects against *some* threaths.

          • Re:No (Score:5, Insightful)

            by growse ( 928427 ) on Tuesday December 20, 2011 @06:52AM (#38432412) Homepage
            Interestingly, the comic isn't making a commentary on the usefulness (or not) of cryptography. It's making fun of people who don't properly evaluate all their threats when they design security systems.
      • Re:No (Score:5, Interesting)

        by Hadlock ( 143607 ) on Tuesday December 20, 2011 @12:48AM (#38430582) Homepage Journal

        I wonder; if I am using gmail, and send an "email" to another gmail user -- both users are required to use https to connect to gmail, does that mean we're in effect using encrypted (RC4_128 according to gmail/chrome) email?

        • Re:No (Score:5, Informative)

          by Oswald ( 235719 ) on Tuesday December 20, 2011 @01:25AM (#38430788)

          I believe that would be a "no" unless you consider parading your message past Google, who probably keeps a bigger file on you than any other entity, private. And it might be a worse than that--saying it's only Google that sees the message assumes that Google doesn't decrypt the message in one facility, send it from that data center to another in the clear, then re-encrypt and send to your recipient. Whose to say your mail server is in the same facility as his just because both accounts are with Google?

          • Re:No (Score:5, Insightful)

            by Hadlock ( 143607 ) on Tuesday December 20, 2011 @01:40AM (#38430896) Homepage Journal

            Whoever has access to your google information, probably has physical access to whatever server your email would sit on otherwise*. I guess it's not an 100% effective means, but in terms of point-to-point email encryption, it's probably the easiest and/or most widely used email encryption scheme avalible to the general public.
            *The old rule that if they have physical access to your machine, your software security is already nullified

            • Re:No (Score:5, Insightful)

              by DarwinSurvivor ( 1752106 ) on Tuesday December 20, 2011 @05:39AM (#38432098)

              *The old rule that if they have physical access to your machine, your software security is already nullified

              That depends on what you are trying to protect. No, software will not prevent them from controlling the machine, copying the HDD, etc, but it CAN prevent them from being able to USE any of that data. Encryption is the ONLY weapon software has against physical access, but it's a VERY effective one if used properly.

        • No you're not using encrypted e-mail. Because your e-mails are stored in clear on Google servers. Which means that Google admins can read your e-mails, and so they can give access to it to other entities that may want it (governments...).
          No, on Gmail your e-mails are not more private than somewhere else.

      • Re:No (Score:5, Informative)

        by mr100percent ( 57156 ) on Tuesday December 20, 2011 @01:37AM (#38430874) Homepage Journal

        That's why there are S/MIME browser plugins like Penango [] for GMail.

      • Pretty much. If the NSA or Gogle wants to snoop on my recipes and Christmas lists, feel free. Anything important goes through the company's servers, so that's their problem. Anything important in my personal life is done with RFC 1149 (I can't afford 2549).

    • by cshark ( 673578 )
      How is it unfortunate? That people aren't buying into transit encryption anymore? It's not the movement of the email you need to worry about. It's what happens when it gets there. If someone steals your computer, email encryption is the least of your worries.
      • Re:No (Score:5, Insightful)

        by hedwards ( 940851 ) on Tuesday December 20, 2011 @12:19AM (#38430406)

        Precisely, when news reports surface of emails being leaked or stolen, rarely if ever do those reports refer to emails being stolen en route. Almost always they're leaked by somebody with access to either the mail server for that domain or the person's own computer.

        Sure one could catch an email en route, but in practice that's hit or miss without having control of the networks to which either the sending or receiving server connects and full knowledge that the email is coming. Without that it's not likely to be profitable to do so as you'd never know which emails to collect.

        • Re:No (Score:5, Insightful)

          by mellon ( 7048 ) on Tuesday December 20, 2011 @12:46AM (#38430562) Homepage

          Turns out that a lot of email leaks to typo domains. So in fact encrypting the email would have been a really good idea in these cases.

          The reason encryption hasn't taken off is that it's not done by default, and can't be enabled by clicking a checkbox.

          • Re:No (Score:4, Insightful)

            by v1 ( 525388 ) on Tuesday December 20, 2011 @01:21AM (#38430754) Homepage Journal

            The reason encryption hasn't taken off is that it's not done by default, and can't be enabled by clicking a checkbox.

            Mac OS X's Mail client automatically supports PGP email certificates on both send and receive. You have to go sign up for one at some place like comodo, and download the cert. Double click and keychain assistant opens up and asks if you want to import it. Setup is complete.

            Now go to your mail app and you will see an open padlock. Any email you send will be automatically signed, and recipients with intelligent email clients will automatically and transparently import your public key into their user's keychain for later use, for both verification of additional received emails and encryption of mail back to you.

            If that person clicks reply, they will also have a padlock available, since their system now has your public key, so they can then send an encrypted reply back to you. If they also have a key pair in their keychain, their reply also includes their public key, allowing you to send them encrypted email in the same way. Of course for maximum security you'd need to have a more personal, direct key exchange rather than email, because a tinfoil hat would argue a skilled black hat could be in between you two when you are trying to exchange keys, and be feeding you two false keys. That's where key-signing parties come in. ;)

            Incredibly easy to use and built-in. Only takes a little effort to go download a free cert from comodo or someone else. What got me into it at first is a previous employer required me to email in my mileage reports for reimbursement, and required me to sign them.

            So at least for the mac users, it's ready by default, and is just a check box away. :)

      • Re:No (Score:5, Insightful)

        by EdIII ( 1114411 ) on Tuesday December 20, 2011 @12:35AM (#38430498)

        Most people are lazy and don't feel they have the need to encrypt their communications. If they are willing to post the shit they do on Facebook, they are already a lost cause from a privacy/anonymity viewpoint.

        Setting up email to send encrypted payloads is not easy for most people, and the people that know how, quickly lose interest after spending an hour to set up one person.

        Now, all of my emails *are* encrypted, and not just in transit. I use a special IMAP connector for Outlook that encrypts all traffic with SSL to the mail server. The web portal for my email server is encrypted with SSL as well. Where *possible* my mail server will negotiate a secure connection to a remote server, but that is pretty damn rare. On my personal computer the message store is located on a TrueCrypt drive, so if my computer is lost or stolen, I am not worried about the message store, which is temporary anyways since the email is stored on the server.

        All of it is pointless if the other party is not doing the same exact thing, which is most of the time. So I never send anything in the clear that I don't want analyzed, categorized, and used by private corporations and government.

        For correspondence that needs to remain secure I usually set up an email account on the same server. That way everything is encrypted down to the message store and emails sent between domains hosted on the same mail server are just internally routed.

        This is the same reason why truly secure phone calls are next to impossible in systems that must be able to perform call setups to any other phone. Too many intermediary points that cannot handle it. ZRTP, while interesting, is a long way from implementation, and will never address insecure endpoints like landlines and cell phones.

        It's the other end that is problem, just as you say, but it is also the points in between. As long as there are free services that won't waste the CPU cycles to negotiate encryption between mail servers, it does not make that much sense.

        Bottom line, I am secure where I need to be, not through encryption specifically, but choosing what I say, when I say it, and what communications medium I choose.

    • Very rarely, alas. (Score:5, Informative)

      by gessel ( 310103 ) * on Tuesday December 20, 2011 @12:47AM (#38430566) Homepage

      I use GPG/OpenPGP for some mail and "secure" web mail for other applications. I do not use third party web mail (such as gmail) because I can't control the dissemination or privacy (or longevity) of my mail and while my life is generally boring enough to fit within Eric Schmidt's idea of privacy ("If you have something that you don't want anyone [someone] to know, maybe you shouldn't be doing it in the first place [at least not though a google property]."), I occasionally write a personal opinion of someone I wouldn't want them to be able to Google later or share a business detail that could be economically damaging or embarrassing (or is subject to NDA) and gMail and all other web mail services are effectively public.

      I've used PGP (and eventually GPG) since about '94 and my keyring has about 20 people on it: more than 1 new key a year! Alas, 25% of those keys expired in the late 90s. My address book has about 1500 entries. Why so few keys? As the OP pointed out, it isn't all that difficult.

      The answer for me is that the model for encouraging encryption has to be more like S-WAN than GPG-like. I'd love to turn on "encrypt everything" and forget it, but I'd get an error message for 99% of my correspondents, so obviously that isn't going to happen. So I set my prefs to reply to encrypted messages with encryption, which is fine, but it means I rarely (almost never) initiate an encrypted thread.

      What I'd like is an opportunistic encryption mode where any message to an address in my keyring is encrypted by default. Any message to anyone I don't have a key for gets a nice little .sig file with a brief notice that their mail is insecure and effectively public and a link to further instructions for getting GPG set up.

      One annoying problem is that encrypted mail is not searchable. To solve that, I want my client to extract a keyword list on decryption then upload that keyword list to (my own) server as an unencrypted header to enable searching (implemented, of course, with a stop list for words you wouldn't want to appear in the clear even out of context or perhaps particularly out of context).

      For the truly paranoid, this list could be a hash list, though you could still fairly effectively dictionary hash fish, but it would provide some security and reduce the easy availability of information. In fact, all headers could be hashed and still generally be searchable (except maybe date ranges).

      I also want my server to store my public key and encrypt all incoming mail with it. Of course it is already transported in the clear, but it makes my server less vulnerable. Once the mail has had an index extracted and the body encrypted, someone cracking into my IMAP server would, at least, not find a historical trove of clear-text data. And my friends without keys would get annoying sig files evangelizing encryption.

      • by mlts ( 1038732 ) * on Tuesday December 20, 2011 @02:05AM (#38431054)

        When it comes down to it, there is no one program that can truly automate good security. At some point, users cannot be spoon fed and have to do it themselves. CAs can be spoofed, trusted introducers can be hacked or bribed, and so on.

        In reality, if you want security these days (I mean actual security, not some pretty spiffy lock icon promising security), then one will have to go out and pack your own parachute, just as people did in the early 1990s.

        It is easier now than it was back then -- gpg and the commercial PGP versions can encrypt and decrypt clipboard contents, both Android and the iPhone have implementations of this. It also easier that the specter of encryption being outlawed is not over our heads as it was back in the days of the Clipper Chip.

        So, it boils to a social issue more than technical now. Do people want to do proper keysigning gatherings, stick their PGP IDs and signatures on their business cards, and have this info as much a part of their contact info as their E-mail address and FB contacts? If we can get people to understand this and the concept of a web of trust, security in general will be much improved.

    • Re:No (Score:5, Funny)

      by PopeRatzo ( 965947 ) * on Tuesday December 20, 2011 @12:56AM (#38430628) Journal

      Nor does anyone else. Unfortunate, but true.

      Are you kidding? I don't even talk to my wife without a Feistel cipher. My daughter's first words were via a one-time pad.

      We're careful in my house.

      Did I ever tell my story (this part is true) about the Bletchley Park alum that my wife worked with when she first got a tenure track position? I don't want to use his name because he passed not too long ago, but when he had office hours for his students, he'd show up in pajama bottoms with burnholes from the pipe he always kept stoked in his mouth. He was a sweet old dude, but you'd wonder how he made it out of the house every morning. In his final few years he was convinced that someone was out to get him and eventually it turned into unnamed Jews who were planning his demise. He was a British subject and there were stories of the stuff he did a Bletchley during the war when he was like 17 or 18 so what do I know? Maybe the Jews were out to get him.

      Anyway, naw, I don't encrypt anything. I have a hard enough time communicating in open text. All of my passwords are my dog's name. I just say the opposite of everything I mean to throw off the New World Order. So when I email my wife, I'll write, "Don't meet me at the 5:10pm train and don't pick up my shirts at the laundry." Neat, huh?

      • Re:No (Score:5, Funny)

        by Anonymous Coward on Tuesday December 20, 2011 @02:19AM (#38431140)

        Anyway, naw, I don't encrypt anything. I have a hard enough time communicating in open text. All of my passwords are my dog's name. I just say the opposite of everything I mean to throw off the New World Order. So when I email my wife, I'll write, "Don't meet me at the 5:10pm train and don't pick up my shirts at the laundry." Neat, huh?

        Same here. The only problem is that our dog does not come when I call. It seems that dogs have a problem recognizing names that are 41 random characters...

      • Re:No (Score:5, Funny)

        by DeBaas ( 470886 ) on Tuesday December 20, 2011 @02:44AM (#38431296) Homepage

        So when I email my wife, I'll write, "Don't meet me at the 5:10pm train and don't pick up my shirts at the laundry." Neat, huh?

        You're probably one of the very few dudes that has a wife that listens..

    • One of the key difficulties is if you are including attachments in encrypted e-mails. This often results in your e-mail being quarantined by (depending on your viewpoint) over judicious anti-virus software as it is unable to scan the encrypted e-mail and guarantee it is virus-free. Your e-mail never arriving rather defeats the purpose of sending it in the first place.

      I appreciate that a well configured system can get round this difficulty, but most end-users do not have well configured systems, they have t
  • No Need.... (Score:4, Insightful)

    by superflit ( 1193931 ) on Monday December 19, 2011 @11:12PM (#38429796) Homepage

    Mostly emails I received are senseless..

    • Re: (Score:3, Insightful)

      by Spritzer ( 950539 ) *
      Exactly! And most that I send. Why would I want to encrypt my email? Then I'd just have to explain to everyone on my contact list how to decrypt a grocery list, joke, forwarded Viagra-gram etc.
  • well (Score:5, Funny)

    by hjf ( 703092 ) on Monday December 19, 2011 @11:12PM (#38429798) Homepage

    I don't. I use GMail. I might as well use "1234" as a password.

    • Re:well (Score:5, Funny)

      by NonUniqueNickname ( 1459477 ) on Monday December 19, 2011 @11:21PM (#38429898)
      May I suggest changing your password to "12345"? It is an order of magnitude safer.
      • Re:well (Score:5, Funny)

        by s4m7 ( 519684 ) on Monday December 19, 2011 @11:32PM (#38430026) Homepage
        So the combination is... one, two, three, four, five? That's the stupidest combination I've ever heard in my life! The kind of thing an idiot would have on his luggage!
        • Re: (Score:3, Funny)

          by aitikin ( 909209 )
          One, two, three, four, five?! That's amazing! I've got the same combination on my luggage!
      • Re:well (Score:5, Insightful)

        by Grishnakh ( 216268 ) on Monday December 19, 2011 @11:45PM (#38430136)

        Seriously speaking, at least with Gmail (or pretty much any other email system out there), you actually have the option of having a password longer than 4 numerical digits, even though it's just for your email. Same goes for most websites; you can have a nice, long secure password on Facebook even though it's only protecting your account where you make inane posts and show stupid pictures of yourself that no one cares about.

        But for protecting your financial transactions, your debit/ATM card limits you to those 4 numerical digits. I think there's something wrong with this picture.

        • Re:well (Score:5, Insightful)

          by Haeleth ( 414428 ) on Monday December 19, 2011 @11:54PM (#38430210) Journal

          The 4-digit PIN normally only applies to buttons that you push with your finger, where brute-force attacks are not really an option. If your bank has ATMs that permit 10,000 attempts before they swallow the card, or uses a 4-digit PIN as a password for their online services, I suggest you take your money elsewhere.

          • This is not true, unless you think the ATM itself is also manually pushing 4 buttons with its finger to authenticate to your bank. Somewhere along the line, that manual action has a digital analogue.

        • Re:well (Score:4, Informative)

          by gman003 ( 1693318 ) on Tuesday December 20, 2011 @12:38AM (#38430520)

          Hell, finance in general is retarded.

          I have a "regular password" that I tend to use for everything (about a year ago, I started adding a use-specific suffix so someone who stole one password wouldn't automatically have the rest).

          It's a fairly secure one, but it includes a _, a $ and a * (as well as a number and letters of both cases). Linux was fine with it. Windows was fine with it. GMail was fine with it. Slashdot was fine with it. Various mailing lists were fine with it. The only things not fine with it?
          Debit card PIN (only four numbers!)
          Voicemail passcode (also only four numbers!)
          Wachovia's online banking system (wait, what?)

          Yep. Wachovia did not allow passwords with symbols. No !@#$%^&* allowed. Just letters and numbers.

          Not only did that significantly decrease password strength (it went from 77^x to 62^x for a given length x), it also made it impossible for me to remember my password. I had to write down instructions on how to regenerate it (change the $ to 4, * to 8, and so on by not using shift, and drop the _ entirely). Most people would've just wrote down their password, making it even more secure.

          Needless to say, I rarely used their website anyways, as it was unimaginably slow as well as pointlessly undersecure. Just waited for the monthly snail-mail summary to check my balance.

          • by rev0lt ( 1950662 )
            Well, I won't argue that, in many cases, finance in general is retarded. Your mileage may vary from corporation to corporation, but it should be noted the system isn't as insecure as one might think:
            - Debit cards use a two-token authentication scheme - the card itself and the pin. Yes, you probably can easily clone the card, and use XKCD's wrench to extract the pin, but that's the client's problem, not the bank. You have no way of allowing a client to access their money in a 100% secure environment (think
    • I don't. I use GMail. I might as well use "1234" as a password.

      GMail actually had a labs feature for a while that enabled PGP signed and encrypted e-mail. Obviously, since the encryption/decryption was done on Google's servers it didn't provide privacy against Google -- but it did provide security against snooping by ISPs, backbone operators, people who might gain access to the recipients e-mail inbox (but not his PGP keys), etc.

      It was discontinued because, I assume, not enough people used it to be worth bothering with. I used it, and configured it to encrypt e-mai

  • No (First Post?) (Score:5, Insightful)

    by Mitreya ( 579078 ) < minus threevowels> on Monday December 19, 2011 @11:12PM (#38429800)
    We email to people who wouldn't know PGP from ABC
    • Re: (Score:3, Insightful)

      by erikjwaxx ( 2013612 )
      This, unfortunately. I encrypt all mail with PGP that it is feasible to encrypt, taking into account the recipient. So that's, literally, one email message, ever.
    • by LoadWB ( 592248 ) on Monday December 19, 2011 @11:19PM (#38429876) Journal

      This. Encrypting email to those who don't know how to decrypt it is useless. And for those who do, email certificates in Outlook work just fine.

      Although, while at a conference I came upon a really nice package call Encryptix (or Encryptics, can't recall which.) It packages up the email, including attachments, encrypts the package, then sends it as an attachment with a link to the viewer. It's trusted by government, so take that for what it's worth to you. And it's not free (yearly subscription, but reasonable) so take that for what it's worth to you.

      Is PGP that easy these days? Haven't touched it in years due to reasons already mentioned.

    • Re: (Score:3, Informative)

      by niftydude ( 1745144 )
      I sign all my email with a PGP signature. No one has ever used it to send me an encrypted email.
    • Re:No (First Post?) (Score:5, Interesting)

      by flaming error ( 1041742 ) on Monday December 19, 2011 @11:43PM (#38430124) Journal

      I was negotiating a mortgage a few years ago, and the bank happily was transitioning from faxes to email. So I sent them all the somewhat sensitive docs they requested, encrypted by hushmail/web. I sent them decryption instructions out of band.

      The pretty simple decryption procedure baffled the hell out of them, at first. Then they figured out it was a great excuse to delay the loan. After a few weeks they came back saying they couldn't follow the hushmail retrieval procedure because they had no internet access.

      Finally I just faxed everything.

      • After a few weeks they came back saying they couldn't follow the hushmail retrieval procedure because they had no internet access.

        I know of one bank that only allows the employees to access only whitelisted web sites on the internet. I wouldn't be surprised if this was the standard security for banks.

    • by mcelrath ( 8027 ) on Tuesday December 20, 2011 @12:12AM (#38430352) Homepage

      More importantly, we email people who's mail server admins don't know PGP from ABC.

      Many years ago I found that my GPG signed mails were getting quarantined by brain-dead spam and virus filters, because my mails contained a "suspicious attachment". That was the death knell for my use of GPG. Not knowing whether your mail will be received is not really acceptable. Of course that's they way it is with all mail these days...but that's the fault of incompetent law enforcement being unable to shut down spam/trojan/botnets.

      PGP was defeated by stupidity.

      • Re:No (First Post?) (Score:5, Informative)

        by langelgjm ( 860756 ) on Tuesday December 20, 2011 @12:43AM (#38430552) Journal
        Exactly. Several years ago, I used to sign e-mails with PGP (not encrypt, just sign). At the time, some Outlook Express clients would red flag this, and display a large, glaring warning to readers about PGP-signed e-mails. Despite the fact that the bug was due to Outlook Express, I stopped using PGP... it's not like I could force all my recipients to a better mail client.
  • Nobody does. Mail with stupid backgrounds and embedded photos abound, but even a signed pgp message never comes across my way

  • Nope (Score:5, Insightful)

    by halo1982 ( 679554 ) * on Monday December 19, 2011 @11:14PM (#38429818) Homepage Journal
    Because no one else does either.
  • Does anyone here encipher their paper mail?
  • and unless you are emailing Richard Stallman with exchanged PGP keys, there are countless systems that look at your emails between here and there. Expecting privacy just doesn't register.
  • No. (Score:5, Insightful)

    by Alrescha ( 50745 ) on Monday December 19, 2011 @11:20PM (#38429878)

    Slashdotters who know enough to have encrypted such things simply don't send that sort of thing in email.


  • by digitalderbs ( 718388 ) on Monday December 19, 2011 @11:20PM (#38429880)
    I've been using PGP for a few years, and on the odd occasion, I'll send an encrypted email to myself. Part of the problem is that no one knows how to use PHP. I've been sending email to thousands of people in an academic setting, and I've only encountered one other person using PGP.

    The reason I keep using PGP, however, is because of digital signing: there's a good guarantee that signed messages were actually sent by me. Headers are fairly trivial to spoof. With PGP, a 'hacker' can only impersonate me if they have access to the private key, which requires physical or ssh access, and he or she must be able to decrypt that key.

    That said, I wish more people would encrypt their messages. This should be a no-brainer in a lot of fields, including human rights and for health and human services, and I think the barrier to commit to email encryption is still too great.
  • the place I worked this summer had it set up (it was an option at my level, maybe it was more mandatory/more necessary elsewhere in the organization
    so I used it on some work email.

    other than that, no.
    not that paranoid, didn't want to set it up, recipients aren't set up to deal with it (even at the office, some recipients had trouble, especially when readign email on their blackberries)

  • What's the point. Orig PGP removed, reposted with offending features changed...accordingly. Ahem

  • by bmo ( 77928 ) on Monday December 19, 2011 @11:22PM (#38429916)

    Encryption is easy

    Getting the people in your address book to encrypt their email is another story. They think that their internet provider's terms of service and privacy policies mean their email is private. This does not take into account other service providers, pipes, and countries along the way that have other ideas about unencrypted streams of text.

    Instant messaging over ssl or other end-to-end encryption (like skype) is more secure, as a result.


    • by Mashiki ( 184564 )

      True to a point, and it's really not hard to understand either. Most people understand websites should have "https" for banking and buying stuff. What's hard, is that you need something else on top of it to encrypt it usually, or a container, or another program. Where as everything else(skype, im, etc) and other end-to-end, which use ssl are seamless. If this was the case for email programs, or webmail, and the like which provided an easy to use repository for *insert key service*, where people could p

  • Ultimately decisions about email encryption come down to what threats you think you might be protecting yourself against. I have a PGP key, and on occasion I use it to sign and decrypt emails when I think it matters. The rest of the time I send mail, over SSL, through my own mail server, which will use SMTP's 'startTLS' command whenever possible. Most people I know read their mail either using SSH on the machine that runs the mail server or over some SSL-protected IMAP or webmail interface. Thus, for most c

  • I've used it with a few friends. Until both mail client software and popular webmail services implement PGP and make its use trivially easy then email encryption will remain a rarity.
  • Well yeah... (Score:5, Interesting)

    by Panaflex ( 13191 ) <convivialdingo AT yahoo DOT com> on Monday December 19, 2011 @11:26PM (#38429954)

    In our business, I routinely communicate with customers using s/mime mail. We set it up as part of the contract (not in the terms, just as part of the meet-n-greet kickoff), so anything related to the contract work goes through encrypted.

    Crypto is our business... so it only makes sense.

  • If your of interest (Score:3, Informative)

    by AHuxley ( 892839 ) on Monday December 19, 2011 @11:27PM (#38429970) Journal
    Your computer will be software or hardware bugged.
    Carrieriq showed the plain text deep state joy of https efforts on your average open or closed US mobile device.
    Sending encrypted mail will just make the NSA more curious.
    Sit down with your family, friends, faith group, business associates and work out a few simple comments that can flow into any text.
  • I tried encrypting my mail for a while, but gave up. Bottom line - I got tired of explaining to people what they needed to do just to read my email.

    Then I tried just digitally signing my email. That caused problems too, because most of our end users have Outlook and Outlook had issues with responding/forwarding when multiple people are involved. A lot of the emails that come my way end up being part of long multi-user threads.

    Now I'm on Gmail, so there's not even an encryption option available. Well, techni

  • Except for work, my email is pretty darn non-interesting to anyone. Well except the ones that contain steganographic payloads, but they don't look encrypted of course :-).

    For internal work email, my employer owns the email system and I connect to it via encrypted connection. Aside from in my browser it never leaves their system. No need for additional encryption.

  • and then.... (Score:5, Insightful)

    by lkcl ( 517947 ) <> on Monday December 19, 2011 @11:29PM (#38429994) Homepage

    ... facebook happened.


  • I'd love to ! (Score:5, Informative)

    by mystik ( 38627 ) on Monday December 19, 2011 @11:31PM (#38430010) Homepage Journal

    My sig (since 2002/2001) on /. has been "Why arn't you encrypting your email?".

    The answer is simple -- there was never a critical mass of people exchanging keys nor was there an easy-to-explain web of trust, nor was there a simple, free reliable certificate authority.

    In 2002, Outlook Express offered integrated s/mime encryption + digital signatures. Once you installed your certificate (which, was simply double clicking a .p12 file, and entering your import password), you could encrypt or sign email going out, with a single click. It verified signatures in inbound email too, all in an integrated UI.

    No one I knew used it.

    Even today; Windows Live mail + Thunderbird offer integrated s/mime encryption. Maybe 1 or 2 of my technically literate friends use it. And of those 2, i think only one persists using it to this day.

    Back then, when all I had was my Palm Pilot IIIxe, I thought "Whoa. I hold in my hand a portable computer that I can use to exchange digital signatures with". I even kept my pgp key in a note I could beam to someone, given the chance. Never happened.

    Nowadays, even AGP on Android doesn't let me exchange keys with someone meet on the street, on the off change they happen to use it. Secure key exchange would be a trivial problem for today's smart phones (provided the carrier isn't using carrieriq to swipe your data....), but there still is no critical mass to make this worthwhile.

    And, with most folks using webmail, You'd have to come up with a hackish way to encrypt mail client side (pgp copy/paste to the clipboard? w/ Rich text? attachments?), or just hand your keys to your provider. Doing the encryption server side would make the service provider an easy target for legal and hacking threats.

    It's a tough nugget to crack, and it's not going to be solved until mail encryption is as easy to use as Facebook.

    • Re:I'd love to ! (Score:4, Interesting)

      by forkazoo ( 138186 ) <> on Tuesday December 20, 2011 @02:57AM (#38431372) Homepage

      In 2002, Outlook Express offered integrated s/mime encryption + digital signatures. Once you installed your certificate (which, was simply double clicking a .p12 file, and entering your import password), you could encrypt or sign email going out, with a single click. It verified signatures in inbound email too, all in an integrated UI.

      Unfortunately, even that's not easy enough for my mom. Nowehere near easy enough, in fact. In order to popularise encrypted email, you have to surrender the idea of out of band key exchange and the concept of web of trust. You also need a highly interoparable way to have it just magically work by default. One good starting place would be a "Public Key At URL" header standard in all email. If you had that, you can imagine a future scenario circa 2015...

      Ordinary corporate email user fires up Outlook 2014. A key has been automatically generated for the user without them knowing it on the Exchange server. Alice sends an ordinary unsecured email to without pushing any extra buttons. This is the first time they have corresponded. Alice's email client includes a header for public-key-location which states that her public key is stored at "". Bob doesn't specifically check email headers, so he just sees a normal email in his inbox. He decides to reply. His email client sees that he is sending to an email address with a known public key location, so it downloads alice's key automatically, and uses it to encrypt bob's message to alice so that only she can read it. This fact manifests itself as a discreet "encrypt" checkbox in the compose email window of bob's mail client. He never needs to manually intervene in the process unless he wants to install a key manually, or actively turn off encryption. Most people would never specifically do that.

      The technology for that kind of infrastructure has been in place for ages. But, there isn't a critical mass that want's it. The security die hards want a system with manual key verification, and user awareness and training. Microsoft might create something similar to what I describe, but it would only work with Outlook and be explicitly incompatible with anything that isn't an Exchange client. And, they would do all decryption server side with decrypted mail stores so IT can audit corporate email. The overwhelming majority of users just don't care. But, basically one of the big players (Microsoft? Google?) needs to create a whole ecosystem in one swoop, with a massive installed base automatically, in order to get any real traction.

      And the rest of us tend to put anything important through a medium other than email. scp for files, ssh tunnels for random things, ssh and talk for nefarious conversations.

  • by Angst Badger ( 8636 ) on Monday December 19, 2011 @11:33PM (#38430038)

    Email is simply not a medium I would even consider using for sending sensitive information precisely because there are countless places between me and my correspondents where a message could be intercepted. In such circumstances, encrypting my email would simply alert anyone watching that something sensitive is being transmitted. And since the only "anyone watching" that I'd worry about is the government, why bother attracting the attention? If they want to know what I'm sending, all they have to do is wait for me to go to work, enter my house, and install a keylogger on my box. It's not like they even need warrants nowadays for that crap.

    If I was going to do something I wanted to hide from the government -- and let's face it, that would almost have to be a major federal felony -- and if I absolutely had to have documentation and accomplices, none of it would be in electronic form to begin with, never mind transmitted over the public internet. Encryption is useful for governments and major corporations that are basically above the law. It's not terribly useful for private citizens unless you're just trying to hide your porn folder from your roommate.

  • I don't (Score:5, Funny)

    by Anonymous Coward on Monday December 19, 2011 @11:38PM (#38430080)

    If I encrypted it the government would start reading it.

  • by GPLHost-Thomas ( 1330431 ) on Monday December 19, 2011 @11:48PM (#38430154)
    Hash: RIPEMD160

    Like every of the ~800 Debian developer in this world, I do use
    encryption, and know how to handle PGP keys. My private key is encrypted
    in a dm-crypt partition of 2 of my laptop, and I have a revoke
    certificate handy burnt on a CD. My GPG fingerprint is also written on
    my business card, so that everyone who I met can fetch my private key
    from any of the major key servers, and check its fingerprint. My public
    key is signed by about a dozen different people, mostly other Debian
    developers, which is a strong "web of trust". If everyone was printing
    his GPG key on a business card, I could also send encrypted emails, but
    I've seen only other DDs doing it.
    Version: GnuPG v1.4.10 (GNU/Linux)
    Comment: Using GnuPG with Mozilla - []

    -----END PGP SIGNATURE-----
    • by mortonda ( 5175 ) on Tuesday December 20, 2011 @12:04AM (#38430276)

      gpg: Signature made Mon Dec 19 21:46:40 2011 CST using DSA key ID 98EF9A49
      gpg: Good signature from ........

      Not posting the rest, but you can get the name and email address from the signature. :) I'd be surprised if any spammers know how to do that though.

    • by gknoy ( 899301 )

      My GPG fingerprint is also written on
      my business card, so that everyone who I met can fetch my private key
      from any of the major key servers, and check its fingerprint.

      Can I have one of your business cards? :D

  • by mortonda ( 5175 ) on Monday December 19, 2011 @11:50PM (#38430170)

    Hash: SHA1

    Why, yes. Yes I do. At least for the few recipients that do too. And
    all my messages are signed.
    Version: GnuPG v1.4.7 (Darwin)
    Comment: Using GnuPG with Mozilla - []

    -----END PGP SIGNATURE-----

  • by cachimaster ( 127194 ) on Monday December 19, 2011 @11:53PM (#38430204)

    If you do software remotely with a group of people, in my experience some kind of email encryption is always used even by non-programmers/managers.
    I have observed technical people is more inclined to use pgp/enigmail solutions while corporate clients tend to use S/MIME.

    Not everything I write is encrypted, but non-encrypted work-related sensible stuff is the exception, not the rule.

  • by triceice ( 1046486 ) on Monday December 19, 2011 @11:56PM (#38430224)

    The average email user doesn't even know what SSL means or why they should only enter their bank passwords after they have verified that they are on a secure site.

    So sure I could encrypt my email but no one would take the steps to actually read it then.

  • by Shoten ( 260439 ) on Monday December 19, 2011 @11:58PM (#38430236)

    The problem is interoperability. Yes, yes...I know, you can just give out your PGP public key to everyone and they'll be able to decrypt their email. If, that is, they use PGP too, which almost nobody does. And granted, can install an S/MIME cert in your copy of Outlook and...what's that? Some people aren't using the full-fledged, Microsoft Office-included version of Outlook? Some people are on smartphones too, and have the AUDACITY to want to be able to read the emails I send them on their iPhones? Bah...idiots. They should focus on more important things than the incredibly sensitive email they send back and encryption!

  • by mr100percent ( 57156 ) on Tuesday December 20, 2011 @01:42AM (#38430900) Homepage Journal

    I've had PGP for over 10 years, but I'm putting it aside and getting behind S/MIME.

    S/MIME has great enterprise support, is built into mail clients like Outlook, OS X Mail, Mozilla Thunderbird, iPhones, iPads, and even has browser plugins for GMail []. PGP has none of this, sadly.

  • by bill_mcgonigle ( 4333 ) * on Tuesday December 20, 2011 @01:59AM (#38431020) Homepage Journal

    Yes, no, maybe.

    I use GPG (Enigmail) for really sensitive stuff but typing my very long passphrase every 15 minutes gets old. Also, those e-mails do not participate in my global search, so I try to keep them as limited as possible. My mail store is on a LUKS volume anyway, so GPG is doing a narrow function.

    Occasionally I'll find somebody who speaks S/MIME, and then that happens automagically for me. That's nice, but largely a function of mailer integration.

    But, in the meantime, a good half of my e-mail, and most of the important stuff, travels out my network on SMTP/STARTTLS connections, so that window of eavesdropping is closing as well.

    Use as much encryption as makes sense (oh, that's the hard part, eh?)

  • by Arancaytar ( 966377 ) <> on Tuesday December 20, 2011 @02:21AM (#38431152) Homepage

    I sign all mail, regardless of whether the recipient has a clue what digital signing even is. In order to encrypt mail, however, both the recipient and the sender must be security aware.

    Practically nobody I communicate with - even among the ones who use Linux - cares enough about security to even own a key, even though they regularly include obviously sensitive information in a message.

Air is water with holes in it.