I am using Postfix 3.1.0 and following instructions at http://www.postfix.org/TLS_README.html#client_smtps <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 inmain.cf <http://main.cf/>, a transport file (hashed) and special routing (relay-smtps) inmaster.cf <http://master.cf/>.

This works - when the onward smtps server accepts the emails. However in my case this doesn't always happen - they sometimes block when we are over quota. So when it fails, Postfix falls back using the hosts specified inmain.cf <http://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 the effect that the email cannot be sent at all.

In short like this:
    /etc/postfix/main.cf <http://main.cf/>
        transport_maps = hash:/etc/postfix/transport
        relayhost = [smtp.sendxxxx.net <http://smtp.sendxxxx.net/>]
smtp_fallback_relay = [relay.gradxxxx.net <http://relay.gradxxxx.net/>] [smtp.sendxxxx.net <http://smtp.sendxxxx.net/>]

/etc/postfix/transport and /etc/postfix/main.cf <http://main.cf/>- as specified atTLS_README.html (above)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.

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