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It's so trivial for Gmail to do PGP that it was testing email signatures two years ago (http://googlesystem.blogspot.com/2009/02/gmail-tests-pgp-signature-verif

by leot 15y ago

It's so trivial for Gmail to do PGP that it was testing email signatures two years ago (http://googlesystem.blogspot.com/2009/02/gmail-tests-pgp-signature-verification.html http://googlesystem.blogspot.com/2009/02/gmail-tests-pgp-sig...) Indeed, Yahoo, Hotmail, and Gmail could get the ball rolling here completely transparently to users and with relative ease, thereby preventing thousands of phishing attacks in the process. If they did, then webmail would suddenly become useful for talking to banks, stockbrokers, foreign dissidents, avoiding craigslist scams, etc. etc.. But not only have Gmail et al not implemented any features like these, but they've not even uttered a peep as to why. Their silence here is conspicuous.

tptacek 15y ago
As someone who uses PGP on a daily basis: I have zero confidence that e.g. my mom could make any sense of it. It doesn't help that Gmail, a web app, has no secure was of implementing PGP with people's "real" public keys. Apple bakes encrypted email into Mail.app. It has an almost transparent UX. Nobody uses it. Demand is what's holding back encrypted email. Nobody cares about it.
- luser001 15y ago
  OK, I'll bite. :) I belong the camp which says Gmail's lack of encryption is "conspicuous". Look at Ubuntu: they're constantly improving the user experience of encrypted home directories. In the latest release, this is as simple as checking a box during account creation (it creates the keys under the hood and uses your login password as the passphrase for the data key etc). Also re: gmail has "no secure way". I read the white paper written by your company on the problems with encryption and javascript. AFAIK, if all traffic is exchanged only over SSL, I don't see any reason why encryption can't be done in Gmail in javascript (unless you're going invoke quality of the random number generators of browsers). Here's an UX I can think of: (1) generate key pairs in the background in the browser for all gmail users. (2) transparently use this to encrypt to users within gmail. Start from there. Then add the ability to import keys of contacts.
  - tptacek 15y ago
    Its feasibility is dubious. Its UX complexity is immense (the comparison to encrypted home directories is tellingly unfair --- if that's the best example of end-user-visible encryption gou can come up with, &c &c). Nobody is asking for it. Few would use it. No other major email vendor does it. You find its absence "conspicuous"?
    - luser001 15y ago
      Hey tptacek, I know you must busy, it's late in the night etc. But it doesn't seem like you really responded to my points: you just seem to be repeating your original assertion that (paraphrasing) "it's too difficult". What aspect of the UX I described do you think is confusing? In the step 0 that I proposed (encryption only within gmail), there is virtually NO UX. Wrt "nobody is asking for it". Then why is ubuntu/windows adding the feature to encrypt dirs? Btw, at a company I worked, they were rolling out SSL certificates to sign email. So I don't agree that "nobody is asking for it". Wrt your point about the comparison being "unfair": I don't think anybody disputes that the "usual" way of doing public-key encryption (rigs of trust etc) is too complex. At the same time, I remember the past when encrypting data dirs was an immense chore. If that UX could be improved, why not the email encryption UX?
      - tptacek 15y ago
        Go ahead and work on it! You have my blessing. The problem of encrypting a home directory is nothing like the problem of implementing a secure, persistent, long-term group messaging system that has to scale up to the entire world.
- leot 15y ago
  Your mom couldn't recognize that a message was "verified" as having come from her Doctor? Or click the "encrypt" box (which causes Gmail to determine whether it knows the public key of every one of an email's recipients). Or click the "sign" box, to add her signature to the email before it sends? Sure, sometimes Gmail would have to say "this email cannot be encrypted because of insufficient information about recipient X". But if anything this might lead to more people using large email providers. Sure, consumers don't know that they want PGP. But when they suddenly discover that can trust that all their messages are seen by only a particular recipient, and that they'll always be able to tell when a message is or isn't from their coworker, they'll quickly start insisting on it the added security.
  - tptacek 15y ago
    Have you ever used PGP for a prolonged period with a changing group of people also using it? I'm inclined to think that someone who'd write a comment like this hasn't. But I could be wrong! Virtually every intra-company mail I send or receive is PGP-encrypted (we're getting to be a fairly big company by HN standards, too). I assure you: my mom could not deal with PGP's (constantly evident) corner cases. How could I possibly think it's a credible solution for the whole world?
    - luser001 15y ago
      Dunno if by PGP you literally mean the PGP/GPG toolkits or something else. I think most of us agree that PGP/GPG suite is too difficult to use. What are the challenges with using public-key encryption with a changing group of people? Key exchange? Remember we're in a more-centralized, always-connected world now wrt email than we were in 1995 (remember offline email writing?). The problem should be simpler now if anything. People have false notions about their email and web traffic in general. The closest previous analogy is shipping packages and letters. There're laws preventing USPS from snooping. People seem to reasonably assuming that that's the case with electronic letters too. And nobody in the mainstream is disabusing of this notion (encryption is mostly shown as being used by terrorists and swindlers). When they become aware of how naked their communications really are, they'll learn how to cope with encryption (including your mom :)).
- nitrogen 15y ago
  Demand is what's holding back encrypted email. Nobody cares about it. I think it's actually a chicken-and-egg problem. The people who care a lot about it can't have it because they need to communicate with everyone else, the people who care a little don't want to bother with using encryption for some contacts and no encryption for others, and the people who don't know and/or don't care don't get any of the benefits. I think two things would make a big difference: 1. marketing end-to-end e-mail encryption as an anti-spam measure, and 2. someone who cares a lot about it implementing an end-to-end, non-government-controllable system that's undeniably easy to use, then releases it for free and gets all the major e-mail platforms to adopt it (obviously much easier said than done).

by leot 15y ago

tptacek 15y ago

As someone who uses PGP on a daily basis: I have zero confidence that e.g. my mom could make any sense of it. It doesn't help that Gmail, a web app, has no secure was of implementing PGP with people's "real" public keys. Apple bakes encrypted email into Mail.app. It has an almost transparent UX. Nobody uses it. Demand is what's holding back encrypted email. Nobody cares about it.

luser001 15y ago
OK, I'll bite. :) I belong the camp which says Gmail's lack of encryption is "conspicuous". Look at Ubuntu: they're constantly improving the user experience of encrypted home directories. In the latest release, this is as simple as checking a box during account creation (it creates the keys under the hood and uses your login password as the passphrase for the data key etc). Also re: gmail has "no secure way". I read the white paper written by your company on the problems with encryption and javascript. AFAIK, if all traffic is exchanged only over SSL, I don't see any reason why encryption can't be done in Gmail in javascript (unless you're going invoke quality of the random number generators of browsers). Here's an UX I can think of: (1) generate key pairs in the background in the browser for all gmail users. (2) transparently use this to encrypt to users within gmail. Start from there. Then add the ability to import keys of contacts.
- tptacek 15y ago
  Its feasibility is dubious. Its UX complexity is immense (the comparison to encrypted home directories is tellingly unfair --- if that's the best example of end-user-visible encryption gou can come up with, &c &c). Nobody is asking for it. Few would use it. No other major email vendor does it. You find its absence "conspicuous"?
  - luser001 15y ago
    Hey tptacek, I know you must busy, it's late in the night etc. But it doesn't seem like you really responded to my points: you just seem to be repeating your original assertion that (paraphrasing) "it's too difficult". What aspect of the UX I described do you think is confusing? In the step 0 that I proposed (encryption only within gmail), there is virtually NO UX. Wrt "nobody is asking for it". Then why is ubuntu/windows adding the feature to encrypt dirs? Btw, at a company I worked, they were rolling out SSL certificates to sign email. So I don't agree that "nobody is asking for it". Wrt your point about the comparison being "unfair": I don't think anybody disputes that the "usual" way of doing public-key encryption (rigs of trust etc) is too complex. At the same time, I remember the past when encrypting data dirs was an immense chore. If that UX could be improved, why not the email encryption UX?
    - tptacek 15y ago
      Go ahead and work on it! You have my blessing. The problem of encrypting a home directory is nothing like the problem of implementing a secure, persistent, long-term group messaging system that has to scale up to the entire world.
leot 15y ago
Your mom couldn't recognize that a message was "verified" as having come from her Doctor? Or click the "encrypt" box (which causes Gmail to determine whether it knows the public key of every one of an email's recipients). Or click the "sign" box, to add her signature to the email before it sends? Sure, sometimes Gmail would have to say "this email cannot be encrypted because of insufficient information about recipient X". But if anything this might lead to more people using large email providers. Sure, consumers don't know that they want PGP. But when they suddenly discover that can trust that all their messages are seen by only a particular recipient, and that they'll always be able to tell when a message is or isn't from their coworker, they'll quickly start insisting on it the added security.
- tptacek 15y ago
  Have you ever used PGP for a prolonged period with a changing group of people also using it? I'm inclined to think that someone who'd write a comment like this hasn't. But I could be wrong! Virtually every intra-company mail I send or receive is PGP-encrypted (we're getting to be a fairly big company by HN standards, too). I assure you: my mom could not deal with PGP's (constantly evident) corner cases. How could I possibly think it's a credible solution for the whole world?
  - luser001 15y ago
    Dunno if by PGP you literally mean the PGP/GPG toolkits or something else. I think most of us agree that PGP/GPG suite is too difficult to use. What are the challenges with using public-key encryption with a changing group of people? Key exchange? Remember we're in a more-centralized, always-connected world now wrt email than we were in 1995 (remember offline email writing?). The problem should be simpler now if anything. People have false notions about their email and web traffic in general. The closest previous analogy is shipping packages and letters. There're laws preventing USPS from snooping. People seem to reasonably assuming that that's the case with electronic letters too. And nobody in the mainstream is disabusing of this notion (encryption is mostly shown as being used by terrorists and swindlers). When they become aware of how naked their communications really are, they'll learn how to cope with encryption (including your mom :)).
nitrogen 15y ago
Demand is what's holding back encrypted email. Nobody cares about it. I think it's actually a chicken-and-egg problem. The people who care a lot about it can't have it because they need to communicate with everyone else, the people who care a little don't want to bother with using encryption for some contacts and no encryption for others, and the people who don't know and/or don't care don't get any of the benefits. I think two things would make a big difference: 1. marketing end-to-end e-mail encryption as an anti-spam measure, and 2. someone who cares a lot about it implementing an end-to-end, non-government-controllable system that's undeniably easy to use, then releases it for free and gets all the major e-mail platforms to adopt it (obviously much easier said than done).