I added the following as Bruce suggested.

debug = 7

I tried doing output = stunnel.log but that cause an error when I reloded the config file.

Here's the log after adding the above and trying to send another email.

2013.06.26 15:03:37 LOG7[10620:10992]: Service [smtps] (FD=416) bound to 0.0.0.0:25

2013.06.26 15:03:58 LOG7[10620:10992]: Service [smtps] accepted (FD=296) from 192.168.1.2:2946

2013.06.26 15:03:58 LOG7[10620:10992]: Creating a new thread

2013.06.26 15:03:58 LOG7[10620:10992]: New thread created

2013.06.26 15:03:58 LOG7[10620:10360]: Service [smtps] started

2013.06.26 15:03:58 LOG5[10620:10360]: Service [smtps] accepted connection from 192.168.1.2:2946

2013.06.26 15:03:58 LOG6[10620:10360]: connect_blocking: connecting 74.125.130.108:465

2013.06.26 15:03:58 LOG7[10620:10360]: connect_blocking: s_poll_wait 74.125.130.108:465: waiting 10 seconds

2013.06.26 15:03:58 LOG5[10620:10360]: connect_blocking: connected 74.125.130.108:465

2013.06.26 15:03:58 LOG5[10620:10360]: Service [smtps] connected remote server from 192.168.1.31:53640

2013.06.26 15:03:58 LOG7[10620:10360]: Remote socket (FD=368) initialized

2013.06.26 15:03:58 LOG7[10620:10360]: SNI: sending servername: smtp.gmail.com

2013.06.26 15:03:58 LOG7[10620:10360]: SSL state (connect): before/connect initialization

2013.06.26 15:03:58 LOG7[10620:10360]: SSL state (connect): SSLv3 write client hello A

2013.06.26 15:03:58 LOG7[10620:10360]: SSL state (connect): SSLv3 read server hello A

2013.06.26 15:03:58 LOG7[10620:10360]: SSL state (connect): SSLv3 read server certificate A

2013.06.26 15:03:58 LOG7[10620:10360]: SSL state (connect): SSLv3 read server done A

2013.06.26 15:03:58 LOG7[10620:10360]: SSL state (connect): SSLv3 write client key exchange A

2013.06.26 15:03:58 LOG7[10620:10360]: SSL state (connect): SSLv3 write change cipher spec A

2013.06.26 15:03:58 LOG7[10620:10360]: SSL state (connect): SSLv3 write finished A

2013.06.26 15:03:58 LOG7[10620:10360]: SSL state (connect): SSLv3 flush data

2013.06.26 15:03:58 LOG7[10620:10360]: SSL state (connect): SSLv3 read server session ticket A

2013.06.26 15:03:58 LOG7[10620:10360]: SSL state (connect): SSLv3 read finished A

2013.06.26 15:03:58 LOG7[10620:10360]: 1 items in the session cache

2013.06.26 15:03:58 LOG7[10620:10360]: 1 client connects (SSL_connect())

2013.06.26 15:03:58 LOG7[10620:10360]: 1 client connects that finished

2013.06.26 15:03:58 LOG7[10620:10360]: 0 client renegotiations requested

2013.06.26 15:03:58 LOG7[10620:10360]: 0 server connects (SSL_accept())

2013.06.26 15:03:58 LOG7[10620:10360]: 0 server connects that finished

2013.06.26 15:03:58 LOG7[10620:10360]: 0 server renegotiations requested

2013.06.26 15:03:58 LOG7[10620:10360]: 0 session cache hits

2013.06.26 15:03:58 LOG7[10620:10360]: 0 external session cache hits

2013.06.26 15:03:58 LOG7[10620:10360]: 0 session cache misses

2013.06.26 15:03:58 LOG7[10620:10360]: 0 session cache timeouts

2013.06.26 15:03:58 LOG7[10620:10360]: Peer certificate was cached (2266 bytes)

2013.06.26 15:03:58 LOG6[10620:10360]: SSL connected: new session negotiated

2013.06.26 15:03:58 LOG6[10620:10360]: Negotiated TLSv1/SSLv3 ciphersuite: AES128-SHA (128-bit encryption)

2013.06.26 15:03:58 LOG6[10620:10360]: Compression: null, expansion: null

2013.06.26 15:03:59 LOG6[10620:10360]: SSL socket closed (SSL_read)

2013.06.26 15:03:59 LOG7[10620:10360]: Sent socket write shutdown

2013.06.26 15:03:59 LOG5[10620:10360]: Connection closed: 65 byte(s) sent to SSL, 293 byte(s) sent to socket

2013.06.26 15:03:59 LOG7[10620:10360]: Remote socket (FD=368) closed

2013.06.26 15:03:59 LOG7[10620:10360]: Local socket (FD=296) closed

2013.06.26 15:03:59 LOG7[10620:10360]: Service [smtps] finished (0 left)

2013.06.26 15:03:59 LOG7[10620:10992]: Service [smtps] accepted (FD=364) from 192.168.1.2:2947

2013.06.26 15:03:59 LOG7[10620:10992]: Creating a new thread

2013.06.26 15:03:59 LOG7[10620:10992]: New thread created

2013.06.26 15:03:59 LOG7[10620:7792]: Service [smtps] started

2013.06.26 15:03:59 LOG5[10620:7792]: Service [smtps] accepted connection from 192.168.1.2:2947

2013.06.26 15:03:59 LOG6[10620:7792]: connect_blocking: connecting 74.125.130.109:465

2013.06.26 15:03:59 LOG7[10620:7792]: connect_blocking: s_poll_wait 74.125.130.109:465: waiting 10 seconds

2013.06.26 15:03:59 LOG5[10620:7792]: connect_blocking: connected 74.125.130.109:465

2013.06.26 15:03:59 LOG5[10620:7792]: Service [smtps] connected remote server from 192.168.1.31:53641

2013.06.26 15:03:59 LOG7[10620:7792]: Remote socket (FD=368) initialized

2013.06.26 15:03:59 LOG7[10620:7792]: SNI: sending servername: smtp.gmail.com

2013.06.26 15:03:59 LOG7[10620:7792]: SSL state (connect): before/connect initialization

2013.06.26 15:03:59 LOG7[10620:7792]: SSL state (connect): SSLv3 write client hello A

2013.06.26 15:03:59 LOG7[10620:7792]: SSL state (connect): SSLv3 read server hello A

2013.06.26 15:03:59 LOG7[10620:7792]: SSL state (connect): SSLv3 read finished A

2013.06.26 15:03:59 LOG7[10620:7792]: SSL state (connect): SSLv3 write change cipher spec A

2013.06.26 15:03:59 LOG7[10620:7792]: SSL state (connect): SSLv3 write finished A

2013.06.26 15:03:59 LOG7[10620:7792]: SSL state (connect): SSLv3 flush data

2013.06.26 15:03:59 LOG7[10620:7792]: 1 items in the session cache

2013.06.26 15:03:59 LOG7[10620:7792]: 2 client connects (SSL_connect())

2013.06.26 15:03:59 LOG7[10620:7792]: 2 client connects that finished

2013.06.26 15:03:59 LOG7[10620:7792]: 0 client renegotiations requested

2013.06.26 15:03:59 LOG7[10620:7792]: 0 server connects (SSL_accept())

2013.06.26 15:03:59 LOG7[10620:7792]: 0 server connects that finished

2013.06.26 15:03:59 LOG7[10620:7792]: 0 server renegotiations requested

2013.06.26 15:03:59 LOG7[10620:7792]: 1 session cache hits

2013.06.26 15:03:59 LOG7[10620:7792]: 0 external session cache hits

2013.06.26 15:03:59 LOG7[10620:7792]: 0 session cache misses

2013.06.26 15:03:59 LOG7[10620:7792]: 0 session cache timeouts

2013.06.26 15:03:59 LOG6[10620:7792]: SSL connected: previous session reused

2013.06.26 15:04:00 LOG6[10620:7792]: SSL socket closed (SSL_read)

2013.06.26 15:04:00 LOG7[10620:7792]: Sent socket write shutdown

2013.06.26 15:04:00 LOG5[10620:7792]: Connection closed: 65 byte(s) sent to SSL, 287 byte(s) sent to socket

2013.06.26 15:04:00 LOG7[10620:7792]: Remote socket (FD=368) closed

2013.06.26 15:04:00 LOG7[10620:7792]: Local socket (FD=364) closed

2013.06.26 15:04:00 LOG7[10620:7792]: Service [smtps] finished (0 left)

2013.06.26 15:04:00 LOG7[10620:10992]: Service [smtps] accepted (FD=372) from 192.168.1.2:2948

2013.06.26 15:04:00 LOG7[10620:10992]: Creating a new thread

2013.06.26 15:04:00 LOG7[10620:10992]: New thread created

2013.06.26 15:04:00 LOG7[10620:12944]: Service [smtps] started

2013.06.26 15:04:00 LOG5[10620:12944]: Service [smtps] accepted connection from 192.168.1.2:2948

2013.06.26 15:04:00 LOG6[10620:12944]: connect_blocking: connecting 74.125.130.108:465

2013.06.26 15:04:00 LOG7[10620:12944]: connect_blocking: s_poll_wait 74.125.130.108:465: waiting 10 seconds

2013.06.26 15:04:00 LOG5[10620:12944]: connect_blocking: connected 74.125.130.108:465

2013.06.26 15:04:00 LOG5[10620:12944]: Service [smtps] connected remote server from 192.168.1.31:53642

2013.06.26 15:04:00 LOG7[10620:12944]: Remote socket (FD=368) initialized

2013.06.26 15:04:00 LOG7[10620:12944]: SNI: sending servername: smtp.gmail.com

2013.06.26 15:04:00 LOG7[10620:12944]: SSL state (connect): before/connect initialization

2013.06.26 15:04:00 LOG7[10620:12944]: SSL state (connect): SSLv3 write client hello A

2013.06.26 15:04:00 LOG7[10620:12944]: SSL state (connect): SSLv3 read server hello A

2013.06.26 15:04:00 LOG7[10620:12944]: SSL state (connect): SSLv3 read finished A

2013.06.26 15:04:00 LOG7[10620:12944]: SSL state (connect): SSLv3 write change cipher spec A

2013.06.26 15:04:00 LOG7[10620:12944]: SSL state (connect): SSLv3 write finished A

2013.06.26 15:04:00 LOG7[10620:12944]: SSL state (connect): SSLv3 flush data

2013.06.26 15:04:00 LOG7[10620:12944]: 1 items in the session cache

2013.06.26 15:04:00 LOG7[10620:12944]: 3 client connects (SSL_connect())

2013.06.26 15:04:00 LOG7[10620:12944]: 3 client connects that finished

2013.06.26 15:04:00 LOG7[10620:12944]: 0 client renegotiations requested

2013.06.26 15:04:00 LOG7[10620:12944]: 0 server connects (SSL_accept())

2013.06.26 15:04:00 LOG7[10620:12944]: 0 server connects that finished

2013.06.26 15:04:00 LOG7[10620:12944]: 0 server renegotiations requested

2013.06.26 15:04:00 LOG7[10620:12944]: 2 session cache hits

2013.06.26 15:04:00 LOG7[10620:12944]: 0 external session cache hits

2013.06.26 15:04:00 LOG7[10620:12944]: 0 session cache misses

2013.06.26 15:04:00 LOG7[10620:12944]: 0 session cache timeouts

2013.06.26 15:04:00 LOG6[10620:12944]: SSL connected: previous session reused

2013.06.26 15:04:01 LOG6[10620:12944]: SSL socket closed (SSL_read)

2013.06.26 15:04:01 LOG7[10620:12944]: Sent socket write shutdown

2013.06.26 15:04:01 LOG5[10620:12944]: Connection closed: 65 byte(s) sent to SSL, 290 byte(s) sent to socket

2013.06.26 15:04:01 LOG7[10620:12944]: Remote socket (FD=368) closed

2013.06.26 15:04:01 LOG7[10620:12944]: Local socket (FD=372) closed

2013.06.26 15:04:01 LOG7[10620:12944]: Service [smtps] finished (0 left)

2013.06.26 15:04:01 LOG7[10620:10992]: Service [smtps] accepted (FD=288) from 192.168.1.2:2949

2013.06.26 15:04:01 LOG7[10620:10992]: Creating a new thread

2013.06.26 15:04:01 LOG7[10620:10992]: New thread created

2013.06.26 15:04:01 LOG7[10620:12900]: Service [smtps] started

2013.06.26 15:04:01 LOG5[10620:12900]: Service [smtps] accepted connection from 192.168.1.2:2949

2013.06.26 15:04:01 LOG6[10620:12900]: connect_blocking: connecting 74.125.130.109:465

2013.06.26 15:04:01 LOG7[10620:12900]: connect_blocking: s_poll_wait 74.125.130.109:465: waiting 10 seconds

2013.06.26 15:04:01 LOG5[10620:12900]: connect_blocking: connected 74.125.130.109:465

2013.06.26 15:04:01 LOG5[10620:12900]: Service [smtps] connected remote server from 192.168.1.31:53643

2013.06.26 15:04:01 LOG7[10620:12900]: Remote socket (FD=368) initialized

2013.06.26 15:04:01 LOG7[10620:12900]: SNI: sending servername: smtp.gmail.com

2013.06.26 15:04:01 LOG7[10620:12900]: SSL state (connect): before/connect initialization

2013.06.26 15:04:01 LOG7[10620:12900]: SSL state (connect): SSLv3 write client hello A

2013.06.26 15:04:01 LOG7[10620:12900]: SSL state (connect): SSLv3 read server hello A

2013.06.26 15:04:01 LOG7[10620:12900]: SSL state (connect): SSLv3 read finished A

2013.06.26 15:04:01 LOG7[10620:12900]: SSL state (connect): SSLv3 write change cipher spec A

2013.06.26 15:04:01 LOG7[10620:12900]: SSL state (connect): SSLv3 write finished A

2013.06.26 15:04:01 LOG7[10620:12900]: SSL state (connect): SSLv3 flush data

2013.06.26 15:04:01 LOG7[10620:12900]: 1 items in the session cache

2013.06.26 15:04:01 LOG7[10620:12900]: 4 client connects (SSL_connect())

2013.06.26 15:04:01 LOG7[10620:12900]: 4 client connects that finished

2013.06.26 15:04:01 LOG7[10620:12900]: 0 client renegotiations requested

2013.06.26 15:04:01 LOG7[10620:12900]: 0 server connects (SSL_accept())

2013.06.26 15:04:01 LOG7[10620:12900]: 0 server connects that finished

2013.06.26 15:04:01 LOG7[10620:12900]: 0 server renegotiations requested

2013.06.26 15:04:01 LOG7[10620:12900]: 3 session cache hits

2013.06.26 15:04:01 LOG7[10620:12900]: 0 external session cache hits

2013.06.26 15:04:01 LOG7[10620:12900]: 0 session cache misses

2013.06.26 15:04:01 LOG7[10620:12900]: 0 session cache timeouts

2013.06.26 15:04:01 LOG6[10620:12900]: SSL connected: previous session reused

2013.06.26 15:04:02 LOG6[10620:12900]: SSL socket closed (SSL_read)

2013.06.26 15:04:02 LOG7[10620:12900]: Sent socket write shutdown

2013.06.26 15:04:02 LOG5[10620:12900]: Connection closed: 65 byte(s) sent to SSL, 293 byte(s) sent to socket

2013.06.26 15:04:02 LOG7[10620:12900]: Remote socket (FD=368) closed

2013.06.26 15:04:02 LOG7[10620:12900]: Local socket (FD=288) closed

2013.06.26 15:04:02 LOG7[10620:12900]: Service [smtps] finished (0 left)

2013.06.26 15:04:02 LOG7[10620:10992]: Service [smtps] accepted (FD=292) from 192.168.1.2:2950

2013.06.26 15:04:02 LOG7[10620:10992]: Creating a new thread

2013.06.26 15:04:02 LOG7[10620:10992]: New thread created

2013.06.26 15:04:02 LOG7[10620:11560]: Service [smtps] started

2013.06.26 15:04:02 LOG5[10620:11560]: Service [smtps] accepted connection from 192.168.1.2:2950

2013.06.26 15:04:02 LOG6[10620:11560]: connect_blocking: connecting 74.125.130.108:465

2013.06.26 15:04:02 LOG7[10620:11560]: connect_blocking: s_poll_wait 74.125.130.108:465: waiting 10 seconds

2013.06.26 15:04:02 LOG5[10620:11560]: connect_blocking: connected 74.125.130.108:465

2013.06.26 15:04:02 LOG5[10620:11560]: Service [smtps] connected remote server from 192.168.1.31:53644

2013.06.26 15:04:02 LOG7[10620:11560]: Remote socket (FD=368) initialized

2013.06.26 15:04:02 LOG7[10620:11560]: SNI: sending servername: smtp.gmail.com

2013.06.26 15:04:02 LOG7[10620:11560]: SSL state (connect): before/connect initialization

2013.06.26 15:04:02 LOG7[10620:11560]: SSL state (connect): SSLv3 write client hello A

2013.06.26 15:04:02 LOG7[10620:11560]: SSL state (connect): SSLv3 read server hello A

2013.06.26 15:04:02 LOG7[10620:11560]: SSL state (connect): SSLv3 read finished A

2013.06.26 15:04:02 LOG7[10620:11560]: SSL state (connect): SSLv3 write change cipher spec A

2013.06.26 15:04:02 LOG7[10620:11560]: SSL state (connect): SSLv3 write finished A

2013.06.26 15:04:02 LOG7[10620:11560]: SSL state (connect): SSLv3 flush data

2013.06.26 15:04:02 LOG7[10620:11560]: 1 items in the session cache

2013.06.26 15:04:02 LOG7[10620:11560]: 5 client connects (SSL_connect())

2013.06.26 15:04:02 LOG7[10620:11560]: 5 client connects that finished

2013.06.26 15:04:02 LOG7[10620:11560]: 0 client renegotiations requested

2013.06.26 15:04:02 LOG7[10620:11560]: 0 server connects (SSL_accept())

2013.06.26 15:04:02 LOG7[10620:11560]: 0 server connects that finished

2013.06.26 15:04:02 LOG7[10620:11560]: 0 server renegotiations requested

2013.06.26 15:04:02 LOG7[10620:11560]: 4 session cache hits

2013.06.26 15:04:02 LOG7[10620:11560]: 0 external session cache hits

2013.06.26 15:04:02 LOG7[10620:11560]: 0 session cache misses

2013.06.26 15:04:02 LOG7[10620:11560]: 0 session cache timeouts

2013.06.26 15:04:02 LOG6[10620:11560]: SSL connected: previous session reused

2013.06.26 15:04:03 LOG6[10620:11560]: SSL socket closed (SSL_read)

2013.06.26 15:04:03 LOG7[10620:11560]: Sent socket write shutdown

2013.06.26 15:04:03 LOG5[10620:11560]: Connection closed: 65 byte(s) sent to SSL, 296 byte(s) sent to socket

2013.06.26 15:04:03 LOG7[10620:11560]: Remote socket (FD=368) closed

2013.06.26 15:04:03 LOG7[10620:11560]: Local socket (FD=292) closed

2013.06.26 15:04:03 LOG7[10620:11560]: Service [smtps] finished (0 left)

2013.06.26 15:04:03 LOG7[10620:10992]: Service [smtps] accepted (FD=296) from 192.168.1.2:2951

2013.06.26 15:04:03 LOG7[10620:10992]: Creating a new thread

2013.06.26 15:04:03 LOG7[10620:10992]: New thread created

2013.06.26 15:04:03 LOG7[10620:10092]: Service [smtps] started

2013.06.26 15:04:03 LOG5[10620:10092]: Service [smtps] accepted connection from 192.168.1.2:2951

2013.06.26 15:04:03 LOG6[10620:10092]: connect_blocking: connecting 74.125.130.109:465

2013.06.26 15:04:03 LOG7[10620:10092]: connect_blocking: s_poll_wait 74.125.130.109:465: waiting 10 seconds

2013.06.26 15:04:03 LOG5[10620:10092]: connect_blocking: connected 74.125.130.109:465

2013.06.26 15:04:03 LOG5[10620:10092]: Service [smtps] connected remote server from 192.168.1.31:53645

2013.06.26 15:04:03 LOG7[10620:10092]: Remote socket (FD=368) initialized

2013.06.26 15:04:03 LOG7[10620:10092]: SNI: sending servername: smtp.gmail.com

2013.06.26 15:04:03 LOG7[10620:10092]: SSL state (connect): before/connect initialization

2013.06.26 15:04:03 LOG7[10620:10092]: SSL state (connect): SSLv3 write client hello A

2013.06.26 15:04:03 LOG7[10620:10092]: SSL state (connect): SSLv3 read server hello A

2013.06.26 15:04:03 LOG7[10620:10092]: SSL state (connect): SSLv3 read finished A

2013.06.26 15:04:03 LOG7[10620:10092]: SSL state (connect): SSLv3 write change cipher spec A

2013.06.26 15:04:03 LOG7[10620:10092]: SSL state (connect): SSLv3 write finished A

2013.06.26 15:04:03 LOG7[10620:10092]: SSL state (connect): SSLv3 flush data

2013.06.26 15:04:03 LOG7[10620:10092]: 1 items in the session cache

2013.06.26 15:04:03 LOG7[10620:10092]: 6 client connects (SSL_connect())

2013.06.26 15:04:03 LOG7[10620:10092]: 6 client connects that finished

2013.06.26 15:04:03 LOG7[10620:10092]: 0 client renegotiations requested

2013.06.26 15:04:03 LOG7[10620:10092]: 0 server connects (SSL_accept())

2013.06.26 15:04:03 LOG7[10620:10092]: 0 server connects that finished

2013.06.26 15:04:03 LOG7[10620:10092]: 0 server renegotiations requested

2013.06.26 15:04:03 LOG7[10620:10092]: 5 session cache hits

2013.06.26 15:04:03 LOG7[10620:10092]: 0 external session cache hits

2013.06.26 15:04:03 LOG7[10620:10092]: 0 session cache misses

2013.06.26 15:04:03 LOG7[10620:10092]: 0 session cache timeouts

2013.06.26 15:04:03 LOG6[10620:10092]: SSL connected: previous session reused

2013.06.26 15:04:04 LOG6[10620:10092]: SSL socket closed (SSL_read)

2013.06.26 15:04:04 LOG7[10620:10092]: Sent socket write shutdown

2013.06.26 15:04:04 LOG5[10620:10092]: Connection closed: 65 byte(s) sent to SSL, 290 byte(s) sent to socket

2013.06.26 15:04:04 LOG7[10620:10092]: Remote socket (FD=368) closed

2013.06.26 15:04:04 LOG7[10620:10092]: Local socket (FD=296) closed

2013.06.26 15:04:04 LOG7[10620:10092]: Service [smtps] finished (0 left)

2013.06.26 15:04:04 LOG7[10620:10992]: Service [smtps] accepted (FD=364) from 192.168.1.2:2952

2013.06.26 15:04:04 LOG7[10620:10992]: Creating a new thread

2013.06.26 15:04:04 LOG7[10620:10992]: New thread created

2013.06.26 15:04:04 LOG7[10620:1404]: Service [smtps] started

2013.06.26 15:04:04 LOG5[10620:1404]: Service [smtps] accepted connection from 192.168.1.2:2952

2013.06.26 15:04:04 LOG6[10620:1404]: connect_blocking: connecting 74.125.130.108:465

2013.06.26 15:04:04 LOG7[10620:1404]: connect_blocking: s_poll_wait 74.125.130.108:465: waiting 10 seconds

2013.06.26 15:04:04 LOG5[10620:1404]: connect_blocking: connected 74.125.130.108:465

2013.06.26 15:04:04 LOG5[10620:1404]: Service [smtps] connected remote server from 192.168.1.31:53646

2013.06.26 15:04:04 LOG7[10620:1404]: Remote socket (FD=368) initialized

2013.06.26 15:04:04 LOG7[10620:1404]: SNI: sending servername: smtp.gmail.com

2013.06.26 15:04:04 LOG7[10620:1404]: SSL state (connect): before/connect initialization

2013.06.26 15:04:04 LOG7[10620:1404]: SSL state (connect): SSLv3 write client hello A

2013.06.26 15:04:05 LOG7[10620:1404]: SSL state (connect): SSLv3 read server hello A

2013.06.26 15:04:05 LOG7[10620:1404]: SSL state (connect): SSLv3 read finished A

2013.06.26 15:04:05 LOG7[10620:1404]: SSL state (connect): SSLv3 write change cipher spec A

2013.06.26 15:04:05 LOG7[10620:1404]: SSL state (connect): SSLv3 write finished A

2013.06.26 15:04:05 LOG7[10620:1404]: SSL state (connect): SSLv3 flush data

2013.06.26 15:04:05 LOG7[10620:1404]: 1 items in the session cache

2013.06.26 15:04:05 LOG7[10620:1404]: 7 client connects (SSL_connect())

2013.06.26 15:04:05 LOG7[10620:1404]: 7 client connects that finished

2013.06.26 15:04:05 LOG7[10620:1404]: 0 client renegotiations requested

2013.06.26 15:04:05 LOG7[10620:1404]: 0 server connects (SSL_accept())

2013.06.26 15:04:05 LOG7[10620:1404]: 0 server connects that finished

2013.06.26 15:04:05 LOG7[10620:1404]: 0 server renegotiations requested

2013.06.26 15:04:05 LOG7[10620:1404]: 6 session cache hits

2013.06.26 15:04:05 LOG7[10620:1404]: 0 external session cache hits

2013.06.26 15:04:05 LOG7[10620:1404]: 0 session cache misses

2013.06.26 15:04:05 LOG7[10620:1404]: 0 session cache timeouts

2013.06.26 15:04:05 LOG6[10620:1404]: SSL connected: previous session reused

2013.06.26 15:04:05 LOG6[10620:1404]: SSL socket closed (SSL_read)

2013.06.26 15:04:05 LOG7[10620:1404]: Sent socket write shutdown

2013.06.26 15:04:05 LOG5[10620:1404]: Connection closed: 65 byte(s) sent to SSL, 290 byte(s) sent to socket

2013.06.26 15:04:05 LOG7[10620:1404]: Remote socket (FD=368) closed

2013.06.26 15:04:05 LOG7[10620:1404]: Local socket (FD=364) closed

2013.06.26 15:04:05 LOG7[10620:1404]: Service [smtps] finished (0 left)

2013.06.26 15:04:05 LOG7[10620:10992]: Service [smtps] accepted (FD=372) from 192.168.1.2:2953

2013.06.26 15:04:05 LOG7[10620:10992]: Creating a new thread

2013.06.26 15:04:05 LOG7[10620:10992]: New thread created

2013.06.26 15:04:05 LOG7[10620:11904]: Service [smtps] started

2013.06.26 15:04:05 LOG5[10620:11904]: Service [smtps] accepted connection from 192.168.1.2:2953

2013.06.26 15:04:05 LOG6[10620:11904]: connect_blocking: connecting 74.125.130.109:465

2013.06.26 15:04:05 LOG7[10620:11904]: connect_blocking: s_poll_wait 74.125.130.109:465: waiting 10 seconds

2013.06.26 15:04:06 LOG5[10620:11904]: connect_blocking: connected 74.125.130.109:465

2013.06.26 15:04:06 LOG5[10620:11904]: Service [smtps] connected remote server from 192.168.1.31:53647

2013.06.26 15:04:06 LOG7[10620:11904]: Remote socket (FD=368) initialized

2013.06.26 15:04:06 LOG7[10620:11904]: SNI: sending servername: smtp.gmail.com

2013.06.26 15:04:06 LOG7[10620:11904]: SSL state (connect): before/connect initialization

2013.06.26 15:04:06 LOG7[10620:11904]: SSL state (connect): SSLv3 write client hello A

2013.06.26 15:04:06 LOG7[10620:11904]: SSL state (connect): SSLv3 read server hello A

2013.06.26 15:04:06 LOG7[10620:11904]: SSL state (connect): SSLv3 read finished A

2013.06.26 15:04:06 LOG7[10620:11904]: SSL state (connect): SSLv3 write change cipher spec A

2013.06.26 15:04:06 LOG7[10620:11904]: SSL state (connect): SSLv3 write finished A

2013.06.26 15:04:06 LOG7[10620:11904]: SSL state (connect): SSLv3 flush data

2013.06.26 15:04:06 LOG7[10620:11904]: 1 items in the session cache

2013.06.26 15:04:06 LOG7[10620:11904]: 8 client connects (SSL_connect())

2013.06.26 15:04:06 LOG7[10620:11904]: 8 client connects that finished

2013.06.26 15:04:06 LOG7[10620:11904]: 0 client renegotiations requested

2013.06.26 15:04:06 LOG7[10620:11904]: 0 server connects (SSL_accept())

2013.06.26 15:04:06 LOG7[10620:11904]: 0 server connects that finished

2013.06.26 15:04:06 LOG7[10620:11904]: 0 server renegotiations requested

2013.06.26 15:04:06 LOG7[10620:11904]: 7 session cache hits

2013.06.26 15:04:06 LOG7[10620:11904]: 0 external session cache hits

2013.06.26 15:04:06 LOG7[10620:11904]: 0 session cache misses

2013.06.26 15:04:06 LOG7[10620:11904]: 0 session cache timeouts

2013.06.26 15:04:06 LOG6[10620:11904]: SSL connected: previous session reused

2013.06.26 15:04:06 LOG6[10620:11904]: SSL socket closed (SSL_read)

2013.06.26 15:04:06 LOG7[10620:11904]: Sent socket write shutdown

2013.06.26 15:04:06 LOG5[10620:11904]: Connection closed: 65 byte(s) sent to SSL, 290 byte(s) sent to socket

2013.06.26 15:04:06 LOG7[10620:11904]: Remote socket (FD=368) closed

2013.06.26 15:04:06 LOG7[10620:11904]: Local socket (FD=372) closed

2013.06.26 15:04:06 LOG7[10620:11904]: Service [smtps] finished (0 left)

From: Stephen Gates [mailto:[email protected]] Sent: Wednesday, June 26, 2013 2:25 PM To: '[email protected]' Subject: Sending Email from PLC Without Authentication with gmail

A customer needs to send emails from a Programmable Logic Controller (PLC) which cannot provide authentication. The customer's email server is gmail which obviously requires authentication.

The PLC IP is 192.168.1.2 and the PC IP on which stunnel is installed is 192.168.1.31

My config is:

cert = stunnel.pem

[smtps]

client = yes

accept = 25

connect = smtp.gmail.com:465

The PLC is set up to send emails to the IP of the PC 192.168.1.31

When I try to send emails I get the following in the stunnel log:

2013.06.26 14:26:30 LOG5[12384:13048]: Service [smtps] accepted connection from 192.168.1.2:2938

2013.06.26 14:26:30 LOG5[12384:13048]: connect_blocking: connected 74.125.130.108:465

2013.06.26 14:26:30 LOG5[12384:13048]: Service [smtps] connected remote server from 192.168.1.31:53599

Any help would be greatly appreciated!

Stephen Gates

Harold K. Scholz Company

7800 Serum Avenue

Ralston, NE 68127

402-339-7600