3 ms·

OK. I'm prepared to agree with the headline in principle. However, here's the deal/problem: I am willing to encrypt outgoing mail only in cases where I can id

by ronaldx 13y ago

OK. I'm prepared to agree with the headline in principle. However, here's the deal/problem: I am willing to encrypt outgoing mail only in cases where I can identify that the recipient are capable of decrypting it (with 0 friction at any stage). It's (still) more important to me that my e-mail is read by the recipient, than that it's not read by any other party.

jimmaswell 13y ago
Do email sites not already use HTTPS?
- jedbrown 13y ago
  Transfer between servers is over SMTP, which is not encrypted by default and almost always subject to degradation attacks (the MITM can claim not to support STARTTLS). In any case, the user cannot verify or demand that STARTTLS be used and many hosts don't support it at all. Meanwhile, PGP does not require any trust of intermediate entities, but relatively few people you might want to email have PGP keys and even those with keys might not have them on the device from which they intend to read your email. S/MIME is in a similar position to PGP, with a CAs trust model instead of Web of Trust.
  - andrewaylett 13y ago
    Note that this is indeed almost always, rather than actually always. My mail server is configured to refuse to send to Google (and a few other hand-picked sites) unless protected by SSL. The converse is, unfortunately, not yet true. DANE[0] should allow me to put DNSSEC secured records in place to tell Google (et al) that they should always use SSL to talk to me too, but I don't have DNSSEC support for my domains yet and my version of Postfix isn't new enough to be able to use it for outgoing mail either. More frustratingly, many popular email providers (for example, BT) don't support SSL at all. That lowers the bar for eavesdropping from active MITM to passive listening. 0: http://www.internetsociety.org/deploy360/resources/dane/ http://www.internetsociety.org/deploy360/resources/dane/
abemassry 13y ago
I'm working on this small project, it might be less friction, probably not zero. I'd be interested if you had any thoughts on how to improve it. It's using GPG for end to end encryption. https://github.com/abemassry/wsend-gpg https://github.com/abemassry/wsend-gpg

by ronaldx 13y ago

jimmaswell 13y ago

Do email sites not already use HTTPS?

jedbrown 13y ago
Transfer between servers is over SMTP, which is not encrypted by default and almost always subject to degradation attacks (the MITM can claim not to support STARTTLS). In any case, the user cannot verify or demand that STARTTLS be used and many hosts don't support it at all. Meanwhile, PGP does not require any trust of intermediate entities, but relatively few people you might want to email have PGP keys and even those with keys might not have them on the device from which they intend to read your email. S/MIME is in a similar position to PGP, with a CAs trust model instead of Web of Trust.
- andrewaylett 13y ago
  Note that this is indeed almost always, rather than actually always. My mail server is configured to refuse to send to Google (and a few other hand-picked sites) unless protected by SSL. The converse is, unfortunately, not yet true. DANE[0] should allow me to put DNSSEC secured records in place to tell Google (et al) that they should always use SSL to talk to me too, but I don't have DNSSEC support for my domains yet and my version of Postfix isn't new enough to be able to use it for outgoing mail either. More frustratingly, many popular email providers (for example, BT) don't support SSL at all. That lowers the bar for eavesdropping from active MITM to passive listening. 0: http://www.internetsociety.org/deploy360/resources/dane/ http://www.internetsociety.org/deploy360/resources/dane/

abemassry 13y ago

I'm working on this small project, it might be less friction, probably not zero. I'd be interested if you had any thoughts on how to improve it. It's using GPG for end to end encryption. https://github.com/abemassry/wsend-gpg https://github.com/abemassry/wsend-gpg