[stunnel-users] Stunnel not receiving connections on ports 465 & 587

James Brown jlbrown at bordo.com.au
Tue Mar 31 03:22:39 CEST 2015

OK, I found out what the problem was - stunnel was not running!

There was nothing in the log to indicate that it was shutting down. Started it up again and everything started to work as before.

One thing I have noticed is that in Mail.app I have to turn on ‘Allow insecure authentication’ as otherwise it will give up after ages, saying that the certificate is invalid.

2015.03.31 11:06:17 LOG7[main]: Service [ssmtp] accepted (FD=3) from
2015.03.31 11:06:17 LOG7[26]: Service [ssmtp] started
2015.03.31 11:06:17 LOG5[26]: Service [ssmtp] accepted connection from
2015.03.31 11:06:17 LOG7[26]: SSL state (accept): before/accept initialization
2015.03.31 11:11:17 LOG6[26]: ssl_start: s_poll_wait: TIMEOUTbusy exceeded: sending reset
2015.03.31 11:11:17 LOG5[26]: Connection reset: 0 byte(s) sent to SSL, 0 byte(s) sent to socket
2015.03.31 11:11:17 LOG7[26]: Local socket (FD=3) closed
2015.03.31 11:11:17 LOG7[26]: Service [ssmtp] finished (0 left)

Mail.app simply logs this:

31/3/2015 11:06:17.520 am Mail[3172]: CFNetwork SSLHandshake failed (-9807)

The client is running Yosemite 10.10.3 latest beta.

Any ideas why it would think it is invalid? Any way to find out?


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