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I'm surprised to see the opposition to self-signed certificates from the EFF. Pushing people towards centralized certificate authorities seems to be anti-freedom. Maybe there is a decentralized approach instead.

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We spent a lot of time thinking about this before we started building Let's Encrypt. In the case of the Web we didn't think there was a way to make self-signed certificates workable for anything because older browsers will always error on them. In the case of mailservers, self-signed certificates work for enabling TLS, and that's great, but you're extremely vulnerable to MITM attacks. So this project offers a way to prevent the MITMs, if you want it.

If there aren't major technical obstacles we might be willing to take pull requests for STARTTLS Everywhere that allow mailservers to announce self-signing policies, but it hasn't been a priority thus far because LE certs are so easy to get and are slightly more authenticated.

The problem with STARTTLS is a mitm downgrade attack. Self-signed certs are exposed to the same kind of mitm attack.

Mail is very sensitive communication. It is reasonable for the EFF to worry the risk of evedropping. Some websites are still sending passwords by email!

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