TLS: SSL_read() failed: error:14094418:SSL routines:SSL3_READ_BYTES:tlsv1 alert unknown ca: SSL alert number 48

Here's a fun error message that we're getting on our mail server at the office:

Aug 15 10:52:26 fvs-pri dovecot: imap-login: Disconnected (no auth attempts in 1 secs): user=<>, rip=172.30.0.221, lip=172.30.0.1, TLS: SSL_read() failed: error:14094418:SSL routines:SSL3_READ_BYTES:tlsv1 alert unknown ca: SSL alert number 48, session=

The odd thing is that using public SSL testing tools (such as the one at DigiCert) do not indicate any problems with the mail server's SSL configuration. And this only seems to affect some clients, and is possibly only acting up with Dovecot. So my guess is that Apache/OpenSSL is configured correctly, but Dovecot is not.

The key to figuring this out is the "openssl s_client" command:

openssl s_client -connect mail.example.com:143 -starttls imap

This showed us that the openssl library was having problems validating the server's certificate, because the intermediate certificates were not also stored in the certificate file that gets sent to the client. The solution is to adjust the file pointed to by Dovecot's "ssl_cert" argument and add your certificate vendor's intermediate certificates to the end of the file.

The order of the certificates inside that file matters. Your server certificate needs to be first, then list the rest of the certificates in order as you move up the certificate chain to the root CA.