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Ask Slashdot: How Do I Request Someone To Send Me a Public Key? 399

First time accepted submitter extraqwert writes "An organization wants me to send them my personal data by email. I certainly do trust them. However, I would like to politely ask them to send me their public key for encryption. The secretary probably does not know what it is. But they do have a pretty good IT department, so they can figure out. My question is, what is the proper wording for such a request? What is the right terminology to use? Should I say ``please send me your RSA key''? ``Public key''? ``PGP key''? Is there a standard and reasonable wording for such a request? (On my end, I am using GNU PGP: ) Any suggestions on how to be polite in this case?"
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Ask Slashdot: How Do I Request Someone To Send Me a Public Key?

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  • by Anonymous Coward on Saturday August 10, 2013 @03:06AM (#44528961)

    Simple and expected processes like this need to be made truly dead simple and nearly automatic. Instead, there are a ton of different formats for keys depending on which the usage and you need to understand a significant amount about what's going on under the covers to do even these kinds of simple actions.

    Incidentally, here's [] the answer to the question. It's anything but clear, but likely to be clearer than any answer you get here.

    • by Octorian ( 14086 ) on Saturday August 10, 2013 @03:16AM (#44529001) Homepage

      And heaven help you if you're using a web-based Email system, which basically breaks all these options. You know, like nearly all "normal" people are now doing.

      • Extensions needed! (Score:5, Insightful)

        by DrYak ( 748999 ) on Saturday August 10, 2013 @06:13AM (#44529507) Homepage

        We need some developers to setup-in and develop in-browser Firefox/Chrome extensions (or userscript, or whatever) that seamlessly integrate encryption into popular webmails.

        You see plain text on the screen, but what actually goes into the "textarea" of the form is encrypted.
        There are already javascript "Rich Text Editors" which do similar jobs (you see a nicely formated text on the screen, but its HTML/BBCode/WikiCode going into the textarea). We simply need something similar, but for encryption and packed into the browser itself through extension mechanisms.

        (Note: Proper security comes from *end to end* encryption. It's therefor mandatory that the encryption/decryption layer is something that the end users install on their browser, and not something provided by the webmail site, even if it's client-side script code. Though it would help if webmail sites provided a few hooks or micro format to simplify the plugin of the encryption layer).

        Bonus point if someone else manage to do the same with OTR and webchats.

        • by AlphaWolf_HK ( 692722 ) on Saturday August 10, 2013 @08:14AM (#44529827)

          Or perhaps we ought to just take email back to the drawing board. Something I've pondered is an "email 2" where encryption is required. In addition, to kill email spam, any server that sends out email could be required to have a DNS record identifying it as an established SMTP server, and all POP3/IMAP servers only trust them instead of just accepting emails from any IP address that probably belongs to grandma's compromised PC. Of course, reverse arpa addresses are considered invalid.

          Webmail providers could do something akin to style vault access, and only the user's password could decrypt the messages they receive. Something to the effect of having the user store the RSA keys on a key fob (or otherwise just keeping them local) and when they log in they decrypt the messages, and then re-encrypt using their vault key and store them on the server.

          Email 2 addresses could be identified by adding say a greater than sign after the @, indicating to the software stack that only secure transmission is permitted, say email2user@>

          That should also take care of your NSA problem, though companies like google would never be on board since they can't keyword match ads to messages.

          • Re: (Score:3, Informative)

            by joshuao3 ( 776721 )
            Your first paragraph is already implemented in something called SPF. It already works using the existing DNS infrastructure. The problem is that creating SPF records is effectively voluntary, so operators of mail servers are only able to use existence of the records as a way to increase trust, and not using the absence of the records as a way to decrease trust. Until everybody is on board with it, unfortunately, it's usefulness will be limited.

            And, just for clarity, a POP3 "server" doesn't accept mail. POP3
          • ... any server that sends out email could be required to have a DNS record identifying it as an established SMTP server, and all POP3/IMAP servers only trust them instead of just accepting emails from any IP address that probably belongs to grandma's compromised PC.

            So, I couldn't run my own private server unless I registered it?

        • by watice ( 1347709 )
          You mean like [] ? Found it in a comment on a similar article this week, have been using it since.
        • Re: (Score:2, Informative)

          The problem I see is that you can send all the encrypted emails you want, but the recipients have to decrypt them. So they need your public key. Everyone needs your public key, and everyone will have your public key. Don't you think the NSA has already started compiling public keys as well?

          What you need to do is have a system that has others' public keys stored, and applies the proper one for whatever email address a message is meant for. Then your message is as safe as the recipient's private key is. Note,

          • No, they don't need the sender's public key to decrypt. The sender encrypts using the recipient's public key which is tied to the recipient's *private* key. That private key is used for decryption. And nobody should have the recipient's private key but the recipient themselves.

            • Not in this scenario(privacy), but it does depend on usage - If I send you an email encrypted with my private key then anyone can read it, but can also be (reasonably) sure the email did in fact come from me and hasn't been tampered with.

              Then there's double-encryption - I encrypt with my private key and then again with your public key - now you're the only one who can decrypt the message, *and* you can confirm that it actually came from me.

              • If I send you an email encrypted with my private key then anyone can read it, but can also be (reasonably) sure the email did in fact come from me and hasn't been tampered with.

                I'm familiar with that as signing, not encrypting.

              • by anagama ( 611277 ) <> on Saturday August 10, 2013 @11:50AM (#44530851) Homepage

                Is there a reason you would use your private key to send encrypted emails to someone? I don't understand.

                My understanding is this:

                A uses B's public key to send message to B, B decrypts with B's private key.

                A slot safe is a better analogy than keys -- anyone can put stuff in the safe's slot, but only the owner who knows the combination can open it and read the messages people put in there.

                But -- maybe you're describing a use scenario I'm not familiar with. And if that is the case, I'd like to understand it.

                • by Immerman ( 2627577 ) on Saturday August 10, 2013 @12:49PM (#44531237)

                  The common term is signing, I should have mentioned that. If you encrypt with your private key it does nothing to hide the message since anyone can decrypt with your public key, but it does let everyone verify that the message did in fact come from you and hasn't been tampered with - the signature is exactly as secure as the encrypted communication channel because it is the exact same mechanism.

                  As an example, let's say the president wanted to send nuclear missile firing orders by email. Now maybe he'd want to keep the orders secret, and he'd encrypt with the missile silo's public key for that. But far more important would be a mechanism in place to verify that the orders actually came from him and not some script kiddie spoofing his email account. That's where the signing comes in - he *also* encrypts his email with his own private key, and the silo can now confirm that the message came from the right person.

                  It's sort of the next step beyond the "secret codeword" confirmation - with a codeword everybody who needs to be able to confirm their orders has to know what the codeword is, and that's a large attack surface for those looking to compromise the system. With digital signing only the president needs to know the codeword, and never tells it to anyone else. Everybody else just needs his public key to confirm that he does in fact know the codeword - thus the system is much more difficult to compromise. That such functionality comes essentially for free with any public/private key encryption channel is an added bonus.

      • As the guy that fixes and sets up PCs 6 days a week I can confirm this, in fact I've only had 2 users still use download mail in the past 5 years and both were retired corporates who were used to Outlook, everybody else? Yahoo and Gmail.

        So if anybody wants encrypted emails to go anywhere there really needs to be some sort of browser based encryption that can work with Yahoo and Gmail, perhaps by making a generic "here is the email" letter with the actual email as an encrypted attachment? Oh and it'll need to be install-able as an app on Android and iOS, because nothing turns folks off more than not being able to check their email on their smartphones and tablets.

        • So using Gmail via IMAP is old school? When I want to be able to access my email from EVERYWHERE? I have the Gmail app on the phone, and I use Thunderbird at home. I have too many email accounts to want to use Webmail for all of it, and I find most webmail GUI's to be horrible.
      • Re: (Score:3, Interesting)

        by Lonewolf666 ( 259450 )

        Encrypted attachment. The mail body only contains the hint that the real data are in the attachment.

        Of course, that won't help you if the recipient is not familiar with using encryption at all...

      • by Anonymous Coward on Saturday August 10, 2013 @08:22AM (#44529847)

        Type the reply on a Royal typewriter and take it to your local post office. Use Certified or Registered mail if you feel squeamish about sending personal information. The NSA can't open a properly mailed letter.

    • by shitzu ( 931108 ) on Saturday August 10, 2013 @04:16AM (#44529209)

      Just as information - in Estonia we have national id cards which have PKCS11 for digital signing and encryption. Everyone already has a key that can be used to encrypt and/or sign data. For instance, the state sends speedcam fines to you via email that are encrypted to your public key and digitally signed by a police officer. Any person can encrypt data to any other person's public key provided that the recipient has an id card with valid certificates. The only caveat is that when the id card expires, the data is unencryptable because new certificates are generated in the new card and then signed by CA.

      • by Anonymous Coward on Saturday August 10, 2013 @05:05AM (#44529339)

        Would this mean that the gov't office that gave you the national ID card is also responsible for generating & storing your private key? If this is the case, it means the gov't has everyone's keys, and the encryption becomes meaningless. :/

        • by Bert64 ( 520050 ) <bert&slashdot,firenzee,com> on Saturday August 10, 2013 @06:01AM (#44529473) Homepage

          Well not in the case given, where you are using the key in order to communicate with the government (eg speeding tickets).

          Banks should really do this, supply their customers with keys (store them on the cards that banks already give to customers) and then all electronic communication to/from the bank is verified using these keys. Should cut down on most of the phishing scams targeting banks.

          • by shitzu ( 931108 ) on Saturday August 10, 2013 @06:41AM (#44529585)

            In Estonia these id cards are used for everything. You can log into banks, you can communicate with any state official. You can sign any contract digitally with them. You can encrypt documents to another person's public key. Etc. This is much simpler than banks and everyone giving out their own cards - i only need one.

            • by Let's All Be Chinese ( 2654985 ) on Saturday August 10, 2013 @07:35AM (#44529731)

              Simpler, yes. Desirable, no. It easily means that everything you do in any context is now easily linked. A state-mandated and -enforced real name policy. This is problematic for the same reasons that facebook or google forcing this on everyone is problematic. There are serious privacy problems with this.

              For example, simply knowing what key a message is encrypted to --and this is generally listed on the outside of a message and thus public-- means that you can do traffic analysis. And so you know which parties are talking to which other parties. Someone getting a lot of messages from the taxman or the state-run fine collector means what, do you think? Or maybe a bank you're trying to get a loan from saw your message stream and now knows that you're also talking to a few other banks, or repo men, or what-have-you. Hmmm.... So even with confidentiality of the contents, you're still leaking information.

              As such, this sort of card is only half the solution, especially since the state mandates that you have to use it, and it is so easy. What we really need is a single system that would support a single card (or multiple cards, if you'd like) with multiple identities.

              I don't strictly mean birth certificate-backed identities, but at least so that you can separate out the loyalty cards and bus passes so that they can sit on the same card yet not tattle on each other. Because each such a card is an "identity" too, carrying a history, and I for one do not want them to be state-enforced on the same identity. In fact, this is the same reason why companies cannot be allowed to gather SSNs without clear law-prescribed purpose, and curiously, that is enshrined in law. Bit of an oversight that this is not.

              No, simply saying "you can't mix that information!" is not enough, because it's unenforcable. You need a system where the holder of the identities can control who gets to see what. If the card doesn't support that, it is deficient, and a danger to its holder.

              • by Nemyst ( 1383049 )
                Um, you do realize that this is all for rather official use cases where you're going to be identified regardless? I doubt your bank only knows you as John Doe, let alone the government. Contracts also tend to require identification.
          • by amiga3D ( 567632 )

            I like that idea. I don't understand why banks aren't doing this.

        • by we3 ( 546328 )

          No, the key would actually be generated on the card, as it has its own cryptographic processor, and cpu. Its called a smart card.

          I have no idea if they are actually doing this, as I am not estonian and am completely unfamiliar with thier ID card issuing process, but he seems to be implying that they do.

          Remember, there are two ways to get a key on a smartcard. You can have it generate a key(which CAN be signed without the key leaving the card), or you can generate the key externally and then import it.

        • by shitzu ( 931108 ) on Saturday August 10, 2013 @06:37AM (#44529563)

          The key pair is generated INSIDE the card. This is the norm with most PKCS11 cards. The private key never leaves the card, your public key is signed by state. So the state does not have your private key per se.
          But that does not necessarily mean they have no means to decrypt it some other way - i don't even pretend to know that.

          • by iluvcapra ( 782887 ) on Saturday August 10, 2013 @06:50AM (#44529605)

            The private key never leaves the card

            Right, and who had possession of the card before you? These sorts of schemes are perfectly fine for government communication, signing contracts, banking, whatever, but they don't provide "4th Amendment Compliant" privacy for things like personal correspondence or use within private and commercial organizations.

          • If there's no way to get the private key out of the card, there's no way to read anything encrypted with your public key when you lose or destroy the card.
            Upside -- you can destroy the card, rendering all private communications to you unreadable.
            Downside -- same thing.
            • by shitzu ( 931108 ) on Saturday August 10, 2013 @09:43AM (#44530187)

              Yup. That's pretty much the case, as i said. You lose the encrypted documents. Generally people don't use it to encrypt day-to-day communitcations. Many people here confuse security and privacy (especially from the government). While our id card system is extremely good and easy for security, its no good for privacy from the governement.

                If i exchanged documents with someone that i want to hide from big brother, i would use PGP. But for legal communications with other individuals or businesses or government, i use the id card system.

          • by wkk2 ( 808881 )

            Also, assumes that the card generates good key pairs and doesn't use some secret process that allows private key recovery from the public key. This has been done by card suppliers in the past.

            As a side questions: Does any CA have a process for signing S/MIME certificates that can be generated outside of a browser?

        • Not entirely. They're acceptable for blocking access by random snoopers. It would be good enough to protect you from everybody except the Estonian government. So for instance thieves -- most peoples' main worry -- wouldn't be able to read your mail.
      • OMG, I want to live in Estonia.
    • Enigmail for Thunderbird has a nice interface for keyservers hidden under some menu if I remember right.

    • by DaveGod ( 703167 )

      I'm just a user but I don't understand why it isn't dead simple and automatic.

      For example, if I put in my recipient field, can't the email client send a standardised request to for the "john" public key? No doubt this leaves room for man-in-the-middle or whatever, but presumably this just means we are now putting email security reliance on existing security systems like SSL or certificates or whatever, rather than nothing at all?

      Most webmail already defaults to SSL logins and could may

      • Most of DNS at this point is too insecure for this to be a workable solution. What do I mean by that? Well, in theory a system called DNSSEC exists that's supposed to ensure you can guarantee a response from any DNS server is correct, that it hasn't been compromized by a MITM attack.

        In practice, it requires involvement from numerous different organizations from the registrars to the DNS hosters, and most simply don't support DNSSEC at all.

        FWIW it's also probably overloading the DNS system to incorpora

    • by sinij ( 911942 )

      Yes, I love PGP and frequently use it, but Entrust has much better system simply because they solved "send me your public key" problem. Unfortunately they solved it by assuming that you belong to a trusted organization, so individual senders are largely out of luck.

  • PGP won't help you (Score:5, Insightful)

    by MichaelSmith ( 789609 ) on Saturday August 10, 2013 @03:15AM (#44528995) Homepage Journal

    The recipient will decrypt you data and lose it or possibly misuse it. That is the risk. But by all means ask for a secure way to get the data to them.

    • by mysidia ( 191772 )

      The recipient will decrypt you data and lose it or possibly misuse it. That is the risk. But by all means ask for a secure way to get the data to them.

      You could always print it out and fax it or snail mail it. Probably more secure. Even if there is now one copy of the data in the trash after they are done with it.

      Maybe talk to them about privacy concerns and ask if their operation has an ISO 27001 info security certification to help validate proven safe handling of data.

    • The same could be said of any method you use. The end result will be a form in which data is outside your hands, in someone else's. whether paper, fax (also paper), optical media, or electronically transmitted by email, it still needs to be in a human readable and understandable format as the end result. And as a result of that... Unless you use the electronic version and have a document management DRM on it, it will always be in a form which can be copied, distributed, and potentially misused.

      The key here

  • It's a lost cause (Score:4, Informative)

    by symbolset ( 646467 ) * on Saturday August 10, 2013 @03:22AM (#44529013) Journal
    If the secretary can find somebody to decrypt your info, she will handle it improperly. Probably scan it directly to their compromised CMS. This is not a company you want to work for.
  • by c0lo ( 1497653 ) on Saturday August 10, 2013 @03:23AM (#44529021)
    Attend or organize a key signing party [].
    • by icebike ( 68054 )

      Not helpful in obtaining a key with which to send email.

      You don't need to trust a key to use it. All you have to do is be assured that the recipient received and was able to read your email. If you communicate with that person via other means you simply ask if they got it.

      • by c0lo ( 1497653 )

        Not helpful in obtaining a key with which to send email.

        You don't need to trust a key to use it. All you have to do is be assured that the recipient received and was able to read your email. If you communicate with that person via other means you simply ask if they got it.

        How do you know the recipient is actually the person you do intend to send messages to?
        If the above is not an issue, why do you use encryption?

  • by rahvin112 ( 446269 ) on Saturday August 10, 2013 @03:24AM (#44529031)

    If they need the information they should have a secure way to receive it. I just refinanced, the broker had a secure site (SSL password protected file vault type interface hosted on their own servers) with a web interface that I could upload documents to.

    If they don't have such a system in place already and routinely request and access peoples personal information your trust is severely misplaced.

    • by hawguy ( 1600213 )

      If they need the information they should have a secure way to receive it. I just refinanced, the broker had a secure site (SSL password protected file vault type interface hosted on their own servers) with a web interface that I could upload documents to.

      If they don't have such a system in place already and routinely request and access peoples personal information your trust is severely misplaced.

      That's not a secure system unless you know how it's protected on the other end. If the uploaded files end up on the corporate fileserver that everyone in the office has access to (including any virus that seeks out SSN's on file shares and emails them to the world, or a rogue employee that figures our that he can increase his income by selling SSN's that he's scraped out of the open fileserver), then it's just the illusion of security. Kind of like those websites that say "Your credit card is safe with us,

      • by rahvin112 ( 446269 ) on Saturday August 10, 2013 @03:51AM (#44529143)

        It's nice you know so much about their system from a single sentence. I especially like the fact that in particular you know so much about their system that it was accessible by anyone other than the loan officer and that you are so certain a virus not only was on their system but that it could scan for SSNs, including of course from scanned documents in PDF format (in other wise a bitmap image).

        Do you often speculate so egregiously about something you do not even know the anything about?

        You act as if you know intimate details of their IT configuration, security procedures and even employee reliability and you don't even know who the bank was (let alone anything else).

        Honestly if I have to worry about the broker (who also happened to be a bank) having employees that are going to run off with my SSN then whether or not the transmission was secure is of little importance. I might add that just because you did it hard copy the same rambling risks you listed still applied to you or do you honestly believe the paper copies you received were the only copies ever made or that those same documents in electronic format weren't stored on their servers?

        • I don't think he is outside the realm of reasonable speculation. Sony had their psn servers compromised and had credit card data ripped off. The connections inbetween were complete secure, but the data still got stolen. It also wasn't a rogue employee either. Data protection laws really need to be tightened up and enforced with auditing. A lot of the stuff is almost as good as cash and should be treated as such.
      • by hymie! ( 95907 )

        Unfortunately, you have no way of controlling, or even knowing, how the receiving company will handle your private information. The best you can do is protect the actual transmission of the information, which SSL should do for you.

  • How? (Score:4, Funny)

    by macraig ( 621737 ) <> on Saturday August 10, 2013 @03:26AM (#44529039)

    How Do I Request Someone To Send Me a Public Key?

    I prefer signal fires myself.

  • If IT sets it up, won't they have the key?

  • by mysidia ( 191772 ) on Saturday August 10, 2013 @03:31AM (#44529063)

    PGP is beyond the grasp of the average secretary or other end user. Unless you know for a fact that the person disseminating the data is familiar with PGP; you should probably not be asking them for their public key.

    I strongly recommend an encrypted PDF, Word Document (.DOCX), or Excel file (.XLSX); make sure to choose a strong password.

    I like the Office 2010 strong encryption and use of key stretching to make brute force password attacks hard --- but there is a free of charge reader available for PDF documents, and you should pick a strong password for encrypted documents anyways.

    Technically, you could implement DRM rights management services on your end, so the user has to contact your organization's RMS server over HTTPS for a license every time the document is opened, but it requires a trust relationship between orgs, or you having an account for the user.

    But the simple password protection is a very nice way to protect it. You can include a note in the e-mail message that you will be calling them to give them the password, so they can see the document.

    Then there is no confusion about what a 'PGP key is'. If you _regularly_ exchange a lot of documents with them, then you might ask to discuss using PGP

    • by jamesh ( 87723 )
      Agree. If you think it's okay for the untrusted secretary or IT department of an organisation to supply the public key then you don't understand public key encryption. Just use a password protected file and supply the password out-of-band.
      • I wouldn't want to trust just the secretary of the other org. However, with public keys (HTTPS, PGP, SSH, anything else similar), it's good for the information on "how to verify" the key to be widely disseminated. For example, the org could put its key fingerprint, and a screenshot of the same as used in common applications, on an indexable part of its HTTPS-protected public website. An individual could put his PGP key fingerprint on his (paper) business card, as fine-print on his resume or CV, and in hi
    • by Pav ( 4298 )
      Bitmessage []?
    • Just don't use Word (.doc). That was some of the stupidest password protecting I have ever seen.

      • by mysidia ( 191772 )

        Just don't use Word (.doc). That was some of the stupidest password protecting I have ever seen.

        Right... the original protection scheme prior to Office 97 was very weak XOR encryption. In Word 2000 it was 56 bit RC4 encryption, which can be brute forced.

        You need to use a Word 2007 or 2010 document format to achieve strong protection, and preferably 2010.

  • by ( 632313 ) on Saturday August 10, 2013 @03:33AM (#44529077)

    I ran into this situation very recently, im in the process of buying a house. It was a bit of a shock to me how much personal information they wanted. And most through email. And how my data is being passed along from business to business without good security.

    I use good practices on my side like two factor authentication, and ssl on everything, even a bit of pgp. But the other side who knows.

  • by bloodhawk ( 813939 ) on Saturday August 10, 2013 @03:35AM (#44529083)
    You are better off just asking for "A secure means to submit your information" and list a few you are happy to use, Maybe they will send you a public key for secure email, maybe a secure web site or maybe they will just say if you are concerned you can get it couriered to them. If they are confused then chances are they have no system in place for dealing with the request and hence not even secure email is any good as that only protects the data in transit which they will certainly load into some HR system somewhere after it gets there anyway.
  • by bscott ( 460706 ) on Saturday August 10, 2013 @03:38AM (#44529095)

    If you don't have the social skills to phrase a polite question, Slashdot is perhaps not the ideal place to go looking for advice...

    Technical issues with giving anyone your private key aside (I can't think of any reason to give it out to someone no matter how much you trust them) just explaining things clearly should work for any reasonable person:

    "I have no problem with you having my personal key, but I am concerned about the integrity of the data while in transit. I would appreciate it if you can supply me with a public key for your organization, then I will be able to encode my key so that only you can decode it. This will ensure that our mutual privacy won't be at risk due to using an insecure communication system such as Email. Thanks very much!" etc

    • by bscott ( 460706 )

      Whoops - I misread the post - they're not asking for your private KEY, just private data... ah well, most of the suggested sentence structure still holds.

  • Every recipient has his or her own private/public key pair. You send an encrypted message to one (or more recipients), and they will be able to read it, nobody else.

    The easiest way to get someone's public key is to convince them to send you a signed message. That is, if your email software can handle it. A signed message contains the sender's public key, and hopefully your email software allows you to stash that key away (automatically) and from then on send encrypted messages to that person.

    Chances a
  • by Xiph1980 ( 944189 ) on Saturday August 10, 2013 @04:06AM (#44529193)
    I'm sorry to say, but the simple fact of the matter is that PGP/GPG isn't used anywhere in corporate life. Not even in banking-related companies.
    For one, people don't perceive email as something that can easily be snooped, and if they do they'll think it's something like a chance encounter as if it's a regular piece of mail where you have to be at a certain point at a certain time to be able to snatch the mail, plus have to have a reasonable idea what you're looking for as a mail thief.
    Secondly, and I cannot stress this enough, it's a f'ing drag to use. It's not easy to install. It's not easy to set up, and it's far from user friendly on a day to day basis.

    Besides the fact that email encryption isn't commonplace, as long as you aren't sending you pin number or medical data on a regular basis (daily), why bother to be honest. You'll get a stamp as "that weird guy" if you start about PGP etc, and that'll last. If you want to send it securely, just wrap it in an encrypted container, like a ZIP or RAR file and phone them the password.
  • S/MIME encrypted email is virtually dead. It was and still is badly implemented in email software (e.g. stuff like searching encrypted messages is usually totally broken) and the ludicrous efforts required to obtain and maintain a key render it useless to all but the most determined person.

    At least with GPG/PGP you can roll a key with no effort and there are public key servers to upload the public key. Persuading someone else to generate such a key and use it is another matter. Probably needs a strong bus

  • by ledow ( 319597 ) on Saturday August 10, 2013 @04:48AM (#44529281) Homepage

    "An organization wants me to send them my personal data by email."

    "But they do have a pretty good IT department"

    No. They don't. Or their IT department is seriously underpowered in terms of getting through to their staff. Don't send personal data by email. If they don't have a system to let you do this (e.g. secured web form, etc.) then their IT department is already a bit of a failure. If they do, their staff would use it and tell you about it.

    If you want to ask, just ask. "I'm not going to send personal data by unencrypted email - what is your procedure for encrypted email?"

    Chances are, they won't have one and will just ask you to send the details unencrypted or by another method entirely.

  • Who cares? That data will end up in a NSA datacenter anyway.
    • Prove it. Prove that every piece of data would end up in a NSA datacenter...that the world we live is in so badly designed that this is necessary.

      If the NSA is hell-bent on compromising the security of day to day operations, then they are acting as an enemy, not a friend. Secure operations, whether personal or corporate, means that ONLY the intended parties can view the damn information...if there are weakened structures placed within for reasons contrary to this, then the data isn't really secure, and as s

      • Well, you look at what happened to Edward Snowden or Bradley Mannings, and you see it personally costs a lot to prove anything, which is why we will not often have proofs.

        I agree with you on NSA role, but I think that the solution is more political than technical. US citizen now have to regain control over their government, and put and end to this massive surveillance state. Such intrusive setup benefit/cost analysis advocates to get it dismantled, as we see other countries that manage to thwart terrorism

  • I don't see why you should be concerned about the request or how "polite" it is. A simple statement to the effect that "I do not send personal information over the Internet without encryption. Please send me instructions as to how your company handles encrypted email. My preferred method is GnuPG, and this will be the quickest and easiest way from my end, but I can try to accommodate other methods."

  • this is really important. people who don't know what ssh keys are will typically send you the id_rsa (private) key file.

    IT IS VERY IMPORTANT that you say to them EXPLICITLY and VERY CLEARLY, "please send me the public key file *only*. DO NOT send me the PRIVATE key. you can identify the private key because it is named xyz. i ONLY want you to send me the PUBLIC key, it is named if you send me the private key, you will have to destroy it and we will have to start again, so ONLY send me the PUBLIC key, ok?"

    and get them to acknowledge what you've said. do not be afraid to "piss them off" by having to be so absolutely specific. make sure you end the sentence with what you *want* them to do, *not* what you *don't* want them to do. depending on the person they could potentially remove the "negative" by their subconscious and do exactly what you ask... with the words "no", "not", "don't" etc. removed.

    also if you want to be paranoid then use the signature-thing (fingerprint). get them to read it out to you over the phone (not by email).

  • This is one of those Slashdot stories where I wish there was a "and they all lived happily ever after?" button on the story where we could all get an instant link to a paragraph or two about how the story finally turned out... because my money is on "they told me to fax it, so I visited the dumpster behind the Smithsonian, found an old fax machine, and sent it to them". It would have been helpful if you could have specified what size of organization (two guys and a lhasa apso? six billion dollar multinatio
  • by X10 ( 186866 ) on Saturday August 10, 2013 @06:59AM (#44529641) Homepage

    I use It's open source, it uses S/MIME, it's server based, and it's easy to use.

  • You're asking how to ask a question? You request them to send a public PGP key so that you can encrypt the email. If they don't know what that means, you elaborate and point them in the right direction.

    The same technique can be extrapolated to any request that you have in life.

  • "The public key may be published without compromising security"
    Source: []

    I had previously written:

    Send the public key in a normal open email and confirm the hash by voice.

    It's the private key that's sensitive and should be kept secure.

    Very annoying to be modded down with no explanation. If you disagree with what I'm posting please reply and explain your position.

    • by fizzup ( 788545 )

      You should not let a missing explanation bother you. You will never get an explanation for any moderation. When you moderate a comment and then submit a comment on the same post, the system undoes your moderation. However, Slashdot's moderation is slightly less ham fisted than most. The system lets you pick a single word that lets the commenter know why his comment is moderated the way it is.

      Your previous comment was moderated "Offtopic." Kudos to the moderator that did it. From the original post,

      My question is, what is the proper wording for such a request?

      You haven'

  • How about just zip the data up, put a strong password on it, call her and tell her the password.
  • And in your email ask them to call you for the password.

  • All these comments so far are missing the K.I.S.S. ( Keep It Simple, Stupid) option. There are physical ways to send electronic data, you can even encrypt it if you wish and send the key and instructions via email, but burn it to a disk or put it on a cheap, small USB key and mail it, duh! Problem solved. The data is still electronic and can be accessed from the media as easily as from an email attachment. What they do with it after that is still bound by the privacy regulations of your country and if you e
  • You havent said if you expect the decryption on the other side to be safe! Is this security only for in-transit? If they are just going to decrypt the data on the other side and plop it in a company share that you are just as much at risk.

  • I was dragged kicking and screaming onto a HIPAA technical implementation task force for a state government about a decade or so ago when HIPAA was first being proposed. We looked at every possible way to encrypt and secure email, both for Data In Transit and for Data at Rest, and the Data In Transit part was intractable. For the situation we had, which was pretty much open with dozens or hundreds of networks sorta kinda on a shared backbone. Too much turf owned by too many players and each went their ow

Order and simplification are the first steps toward mastery of a subject -- the actual enemy is the unknown. -- Thomas Mann