I am using Postfix 3.1.0 and following instructions at http://www.postfix.org/TLS_README.html#client_smtps to set up for sending some (recipient dependent) emails via smtps (whereas others go over TLS to a different relay server). This uses the transport_maps settings in main.cf, a transport file (hashed) and special routing (relay-smtps) in master.cf.
This works - when the onward smtps server accepts the emails. However in my case this doesn't always happen - basically they sometimes block when we are over quota. So when it fails, Postfix falls back using the hosts specified in main.cf's smtp_fallback_relay (*not* relayhost, which is used for emails that don't have a match in the transport list). All well and good. But I find that after smtps rejection, the fallback_relay hosts (both) always fail too with message like: warning: TLS library problem: error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol:s23_clnt.c:794: With effect that the email cannot be sent at all. In short like this: /etc/postfix/main.cf transport_maps = hash:/etc/postfix/transport relayhost = [smtp.sendxxxx.net] smtp_fallback_relay = [relay.gradxxxx.net] [smtp.sendxxxx.net] /etc/postfix/transport and /etc/postfix/main.cf - as specified at http://www.postfix.org/TLS_README.html#client_smtps for Postfix >= 3.0 However if I remove the initial attempt to use smtps (i.e. comment out transport_maps and reload postfix), then relayhost and fallback_relays work perfectly. I've tried a raft of different settings without success. Any suggestions gratefully received. Dominic