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I recently had a problem getting STARTTLS working on exim4 on Debian 4.0 (Etch). It kept reporting:

TLS error on connection from host (ehlo) [ip]
(cert/key setup: cert=/etc/ssl/certs/whatever.crt key=/etc/ssl/private/whatever.key:
Base64 decoding error.

This was confirmed by running gnutls-serv --debug 5 --x509certfile foo.crt --x509keyfile foo.key, which reported the same error.

I've recently been struggling to reliably send email via my qmail server. I've got STARTTLS and SMTP AUTH enabled, in order to allow relaying for authenticated users. However, it's been really slow, and Thunderbird quite often times out and gives up on the connection.

Lucky part 13 of Installing qmail and vpopmail. This one talks about SMTP-over-TLS.

Part 11 of Installing qmail and vpopmail. This part is about securing webmail access by using HTTPS.

Part 10 of Installing qmail and vpopmail. This part talks about installing a virus scanner to check mail before it's delivered.

Part 9 of Installing qmail and vpopmail.

Part 8 of Installing qmail and vpopmail.

Part 7 of Installing qmail and vpopmail.

Part 6 of Installing qmail and vpopmail.

Part 5 of Installing qmail and vpopmail.