On Fri, Mar 29, 2013 at 06:16:54AM -0600, sulli...@indra.com wrote:
> I'm trying to set up a simple email relay host, with my home
> linux box sending to smtp.indra.com.
> I'm running Postfix 2.9.6-1~12.1 on Xubuntu 3.5.0.26,
> and I need to use SSL to talk to indra.
> 
> I think SSL works on port 465 because I can use openssl to connect:
> 
> openssl s_client -crlf -connect smtp.indra.com:465
> AUTH LOGIN
> 334 VXNlcm5hbWU6     # base64 prompt for "Userid:"
> (send my base64 userid)
> 334 UGFzc3dvcmQ6     # base64 prompt for "Password:"
> (send my base64 password)
> 235 2.0.0 OK Authenticated
> 
> I tried to do this in postfix, by using
>   main.cf:
>     relayhost = smtp.indra.com:465

This should be the bracketed form as you used below, to inhibit MX 
lookup of the name. Also, the smtp_sasl_password_maps entry must 
exactly match the relayhost; this could be the reason why you didn't 
authenticate.

>     smtp_sasl_auth_enable = yes
>     smtp_sasl_mechanism_filter = login
>     smtp_sasl_password_maps = hash:/etc/postfix/sasl/passwd
>   sasl/passwd:
>     [smtp.indra.com]:465 lastName:myPasswd

Like this.

>   postmap sasl/passwd
>   service postfix restart
> 
> I get in /var/log/mail.log:
> 
>   Mar 28 14:22:02 helix postfix/smtp[10392]: CLIENT wrappermode 
> (port smtps/465) is unimplemented

There is a workaround using stunnel(1) which is documented in 
TLS_README.html#client_smtps , but you should follow this advice:

>   Mar 28 14:22:02 helix postfix/smtp[10392]: instead, send to (port
> submission/587) with STARTTLS

... and get STARTTLS working on 587. You did not show any evidence 
that you tried to do that.

http://www.postfix.org/TLS_README.html#client_tls

> When I change to the port from 465 to 587 in the above 2 files
> and restart postfix, I get in /var/log/mail.log:
> 
> Mar 29 06:09:33 helix postfix/pickup[5513]: A06D318122B: uid=5555
> from=<firstname.lastn...@mathcom.com>
> Mar 29 06:09:33 helix postfix/cleanup[5726]: A06D318122B:
> message-id=<20130329120933.ga5...@mathcom.com>
> Mar 29 06:09:33 helix postfix/qmgr[10564]: A06D318122B:
> from=<firstname.lastn...@mathcom.com>, size=611, nrcpt=1 (queue active)
> Mar 29 06:09:40 helix postfix/smtp[5728]: A06D318122B:
> to=<lastn...@indra.com>, relay=smtp.indra.com[209.169.0.20]:587,
> delay=7.2, delays=0.09/0/6.9/0.14, dsn=4.7.1, status=SOFTBOUNCE (host
> smtp.indra.com[209.169.0.20] said: 550 5.7.1 <lastn...@indra.com>...
> Access denied (in reply to RCPT TO command))
> 
> 
> # postqueue -p
> -Queue ID- --Size-- ----Arrival Time---- -Sender/Recipient-------
> A06D318122B      611 Fri Mar 29 06:09:33  firstname.lastn...@mathcom.com
> (host smtp.indra.com[209.169.0.20] said: 550 5.7.1 <lastn...@indra.com>...
> Access denied (in reply to RCPT TO command))
>                                          lastn...@indra.com
> 
> Any thoughts?

If this isn't enough to get you going, see here before posting again:

http://www.postfix.org/DEBUG_README.html#mail
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