Hopefully I'm saving someone else time asking these gmail interop 
questions.

I'm testing to see whether I can send via SSL on port 465, but it seems
to result in timeouts. I'm guessing there is some confusion in the SMTP
dialog, however it's encrypted, so I can't snoop. Any pointers on how I
could troubleshoot this?

Setting ESMTP_LOG_DIALOG=1 does not produce any extra output that I can
find in this version either. Does this option work?

Courier mta/ssl version: 0.63.0, from Ubuntu Lucid / 10.04

mail.log:
Jun  7 16:24:00 foohost courieresmtp: 
id=0001B9B7.4C0D541E.00003633,from=<r...@foohost>,addr=<[email protected]>: 
Connection timed out
Jun  7 16:24:00 foohost courieresmtp: 
id=0001B9B7.4C0D541E.00003633,from=<r...@foohost>,addr=<[email protected]>,status:
 deferred

I've tried the following settings:

    esmtproutes:
    :smtp.gmail.com,465

    esmtpauthclient:
    smtp.gmail.com,465 [email protected] xxxxx

And:

    esmtproutes:
    :smtp.gmail.com,465/SECURITY=NONE

    esmtpauthclient:
    smtp.gmail.com,465/SECURITY=NONE [email protected] xxxxx

I also tried setting ESMTP_USE_STARTTLS=1 to 0 in courierd

Related files:

esmtpd:

PATH=/usr/bin:/bin:/usr/bin:/usr/local/bin
SHELL=/bin/bash
ULIMIT=16384
BOFHCHECKDNS=1
BOFHNOEXPN=1
BOFHNOVRFY=1
NOADDMSGID=1
NOADDDATE=1
ESMTP_LOG_DIALOG=0
AUTH_REQUIRED=0
COURIERTLS=/usr/bin/couriertls
TLS_KX_LIST=ALL
TLS_COMPRESSION=ALL
TLS_CERTS=X509
TLS_CERTFILE=/etc/courier/esmtpd.pem
TLS_TRUSTCERTS=/etc/ssl/certs
TLS_VERIFYPEER=NONE
MAILUSER=daemon
MAILGROUP=daemon
PORT=smtp
BLACKLISTS=""
ACCESSFILE=${sysconfdir}/smtpaccess
MAXDAEMONS=40
MAXPERC=5
MAXPERIP=5
PIDFILE=/var/run/courier/esmtpd.pid
TCPDOPTS="-stderrlogger=/usr/sbin/courierlogger"
ESMTPAUTH=""
ESMTPAUTH_WEBADMIN="LOGIN CRAM-MD5 CRAM-SHA1 CRAM-SHA256"
ESMTPAUTH_TLS=""
ESMTPAUTH_TLS_WEBADMIN="PLAIN LOGIN CRAM-MD5 CRAM-SHA1 CRAM-SHA256"
ESMTPDSTART=YES

courierd:

refix="/usr"
exec_prefix="/usr"
PATH=/usr/bin:/bin:/usr/bin:/usr/local/bin
SHELL=/bin/bash
DSNTOAUTHADDR=0
DYNAMICDELIVERIES=1
DEFAULTDELIVERY=./Maildir
MAILDROPDEFAULT=./Maildir
ESMTP_CORK=1
ESMTP_BLOCKBACKSCATTER=smtp/dsn
UUXFLAGS="-j -g C"
ESMTP_USE_STARTTLS=1
LC_ALL=C
COURIERTLS=/usr/bin/couriertls
ESMTP_TLS_VERIFY_DOMAIN=0
TLS_KX_LIST=ALL
TLS_COMPRESSION=ALL
TLS_CERTS=X509
TLS_TRUSTCERTS=/etc/ssl/certs
TLS_VERIFYPEER=NONE

Cheers,
spd

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