Ricardo Kleemann writes:

$ openssl s_client -starttls smtp -connect localhost:25 -ssl3
CONNECTED(00000003)
19951:error:14094410:SSL routines:SSL3_READ_BYTES:sslv3 alert handshake
failure:s3_pkt.c:1053:SSL alert number 40
19951:error:1409E0E5:SSL routines:SSL3_WRITE_BYTES:ssl handshake
failure:s3_pkt.c:530:

Using tls1 gives me errors of certificate expired, but at the same time I'd
like to understand why ssl2 and ssl3 are failing.

You are using the above openssl client. Confirm whether Courier itself is built against OpenSSL or GnuTLS. The only thing I can think of would be a problem with OpenSSL talking to GnuTLS.

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