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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

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.

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.