I am attempting to send/receive to GMail through a CRM program (contains email client) called ACT! (http://www.act.com)  ACT! only allows server addresses in the program configuration, NOT port numbers.  (e.g. smtp.gmail.com or 127.0.0.1 - nothing else)
 
I have configured stunnel 4.26 as such:
 
; Some performance tunings
socket = l:TCP_NODELAY=1
socket = r:TCP_NODELAY=1
; Some debugging stuff useful for troubleshooting
debug = 7
output = stunnel.log
; Use it for client mode
client = yes
; Service-level configuration
[pop]
accept = localhost:110
connect = pop.gmail.com:995
[smtp]
accept = localhost:25
connect = smtp.gmail.com:465
 
and in ACT as such:
SMTP as localhost
POP as localhost
 
(also have tried 127.0.0.1, but with no difference).
 
The log is below, but the short of it is that I still cannot get through to the GMail servers.  I do not see any glaring errors below, but I'm sure there is something useful.  Thank you for any help...
 
 
2009.02.24 13:34:35 LOG7[3752:2216]: RAND_status claims sufficient entropy for the PRNG
2009.02.24 13:34:35 LOG7[3752:2216]: PRNG seeded successfully
2009.02.24 13:34:35 LOG7[3752:2216]: SSL context initialized for service pop
2009.02.24 13:34:35 LOG7[3752:2216]: SSL context initialized for service smtp
2009.02.24 13:34:35 LOG5[3752:2216]: stunnel 4.26 on x86-pc-mingw32-gnu with OpenSSL 0.9.8i 15 Sep 2008
2009.02.24 13:34:35 LOG5[3752:2216]: Threading:WIN32 SSL:ENGINE Sockets:SELECT,IPv6
2009.02.24 13:34:35 LOG5[3752:1576]: No limit detected for the number of clients
2009.02.24 13:34:35 LOG7[3752:1576]: FD 200 in non-blocking mode
2009.02.24 13:34:35 LOG7[3752:1576]: SO_REUSEADDR option set on accept socket
2009.02.24 13:34:35 LOG7[3752:1576]: pop bound to 127.0.0.1:110
2009.02.24 13:34:35 LOG7[3752:1576]: FD 208 in non-blocking mode
2009.02.24 13:34:35 LOG7[3752:1576]: SO_REUSEADDR option set on accept socket
2009.02.24 13:34:35 LOG7[3752:1576]: smtp bound to 127.0.0.1:25
2009.02.24 13:34:39 LOG7[3752:1576]: smtp accepted FD=216 from 127.0.0.1:3063
2009.02.24 13:34:39 LOG7[3752:1576]: Creating a new thread
2009.02.24 13:34:39 LOG7[3752:1576]: New thread created
2009.02.24 13:34:39 LOG7[3752:760]: smtp started
2009.02.24 13:34:39 LOG7[3752:760]: FD 216 in non-blocking mode
2009.02.24 13:34:39 LOG7[3752:760]: TCP_NODELAY option set on local socket
2009.02.24 13:34:39 LOG5[3752:760]: smtp accepted connection from 127.0.0.1:3063
2009.02.24 13:34:39 LOG7[3752:760]: FD 240 in non-blocking mode
2009.02.24 13:34:39 LOG7[3752:760]: smtp connecting 209.85.201.111:465
2009.02.24 13:34:39 LOG7[3752:760]: connect_wait: waiting 10 seconds
2009.02.24 13:34:39 LOG7[3752:760]: connect_wait: connected
2009.02.24 13:34:39 LOG5[3752:760]: smtp connected remote server from 192.168.1.100:3064
2009.02.24 13:34:39 LOG7[3752:760]: Remote FD=240 initialized
2009.02.24 13:34:39 LOG7[3752:760]: TCP_NODELAY option set on remote socket
2009.02.24 13:34:39 LOG7[3752:760]: SSL state (connect): before/connect initialization
2009.02.24 13:34:39 LOG7[3752:760]: SSL state (connect): SSLv3 write client hello A
2009.02.24 13:34:39 LOG7[3752:760]: SSL state (connect): SSLv3 read server hello A
2009.02.24 13:34:39 LOG7[3752:760]: SSL state (connect): SSLv3 read server certificate A
2009.02.24 13:34:39 LOG7[3752:760]: SSL state (connect): SSLv3 read server done A
2009.02.24 13:34:39 LOG7[3752:760]: SSL state (connect): SSLv3 write client key exchange A
2009.02.24 13:34:39 LOG7[3752:760]: SSL state (connect): SSLv3 write change cipher spec A
2009.02.24 13:34:39 LOG7[3752:760]: SSL state (connect): SSLv3 write finished A
2009.02.24 13:34:39 LOG7[3752:760]: SSL state (connect): SSLv3 flush data
2009.02.24 13:34:39 LOG7[3752:760]: SSL state (connect): SSLv3 read finished A
2009.02.24 13:34:39 LOG7[3752:760]:    1 items in the session cache
2009.02.24 13:34:39 LOG7[3752:760]:    1 client connects (SSL_connect())
2009.02.24 13:34:39 LOG7[3752:760]:    1 client connects that finished
2009.02.24 13:34:39 LOG7[3752:760]:    0 client renegotiations requested
2009.02.24 13:34:39 LOG7[3752:760]:    0 server connects (SSL_accept())
2009.02.24 13:34:39 LOG7[3752:760]:    0 server connects that finished
2009.02.24 13:34:39 LOG7[3752:760]:    0 server renegotiations requested
2009.02.24 13:34:39 LOG7[3752:760]:    0 session cache hits
2009.02.24 13:34:39 LOG7[3752:760]:    0 session cache misses
2009.02.24 13:34:39 LOG7[3752:760]:    0 session cache timeouts
2009.02.24 13:34:39 LOG6[3752:760]: SSL connected: new session negotiated
2009.02.24 13:34:39 LOG6[3752:760]: Negotiated ciphers: RC4-MD5 SSLv3 Kx=RSA Au=RSA Enc=RC4(128) Mac=MD5
2009.02.24 13:34:39 LOG7[3752:760]: SSL socket closed on SSL_read
2009.02.24 13:34:39 LOG7[3752:760]: Socket write shutdown
2009.02.24 13:34:39 LOG5[3752:760]: Connection closed: 20 bytes sent to SSL, 226 bytes sent to socket
2009.02.24 13:34:39 LOG7[3752:760]: smtp finished (0 left)
2009.02.24 13:34:39 LOG7[3752:1576]: pop accepted FD=232 from 127.0.0.1:3065
2009.02.24 13:34:39 LOG7[3752:1576]: Creating a new thread
2009.02.24 13:34:39 LOG7[3752:1576]: New thread created
2009.02.24 13:34:39 LOG7[3752:376]: pop started
2009.02.24 13:34:39 LOG7[3752:376]: FD 232 in non-blocking mode
2009.02.24 13:34:39 LOG7[3752:376]: TCP_NODELAY option set on local socket
2009.02.24 13:34:39 LOG5[3752:376]: pop accepted connection from 127.0.0.1:3065
2009.02.24 13:34:39 LOG7[3752:376]: FD 240 in non-blocking mode
2009.02.24 13:34:39 LOG7[3752:376]: pop connecting 209.85.147.109:995
2009.02.24 13:34:39 LOG7[3752:376]: connect_wait: waiting 10 seconds
2009.02.24 13:34:42 LOG7[3752:376]: connect_wait: connected
2009.02.24 13:34:42 LOG5[3752:376]: pop connected remote server from 192.168.1.100:3066
2009.02.24 13:34:42 LOG7[3752:376]: Remote FD=240 initialized
2009.02.24 13:34:42 LOG7[3752:376]: TCP_NODELAY option set on remote socket
2009.02.24 13:34:42 LOG7[3752:376]: SSL state (connect): before/connect initialization
2009.02.24 13:34:42 LOG7[3752:376]: SSL state (connect): SSLv3 write client hello A
2009.02.24 13:34:42 LOG7[3752:376]: SSL state (connect): SSLv3 read server hello A
2009.02.24 13:34:42 LOG7[3752:376]: SSL state (connect): SSLv3 read server certificate A
2009.02.24 13:34:42 LOG7[3752:376]: SSL state (connect): SSLv3 read server done A
2009.02.24 13:34:42 LOG7[3752:376]: SSL state (connect): SSLv3 write client key exchange A
2009.02.24 13:34:42 LOG7[3752:376]: SSL state (connect): SSLv3 write change cipher spec A
2009.02.24 13:34:42 LOG7[3752:376]: SSL state (connect): SSLv3 write finished A
2009.02.24 13:34:42 LOG7[3752:376]: SSL state (connect): SSLv3 flush data
2009.02.24 13:34:42 LOG7[3752:376]: SSL state (connect): SSLv3 read finished A
2009.02.24 13:34:42 LOG7[3752:376]:    1 items in the session cache
2009.02.24 13:34:42 LOG7[3752:376]:    1 client connects (SSL_connect())
2009.02.24 13:34:42 LOG7[3752:376]:    1 client connects that finished
2009.02.24 13:34:42 LOG7[3752:376]:    0 client renegotiations requested
2009.02.24 13:34:42 LOG7[3752:376]:    0 server connects (SSL_accept())
2009.02.24 13:34:42 LOG7[3752:376]:    0 server connects that finished
2009.02.24 13:34:42 LOG7[3752:376]:    0 server renegotiations requested
2009.02.24 13:34:42 LOG7[3752:376]:    0 session cache hits
2009.02.24 13:34:42 LOG7[3752:376]:    0 session cache misses
2009.02.24 13:34:42 LOG7[3752:376]:    0 session cache timeouts
2009.02.24 13:34:42 LOG6[3752:376]: SSL connected: new session negotiated
2009.02.24 13:34:42 LOG6[3752:376]: Negotiated ciphers: RC4-MD5 SSLv3 Kx=RSA Au=RSA Enc=RC4(128) Mac=MD5
2009.02.24 13:34:42 LOG7[3752:1576]: smtp accepted FD=264 from 127.0.0.1:3067
2009.02.24 13:34:42 LOG7[3752:1576]: Creating a new thread
2009.02.24 13:34:42 LOG7[3752:1576]: New thread created
2009.02.24 13:34:42 LOG7[3752:216]: smtp started
2009.02.24 13:34:42 LOG7[3752:216]: FD 264 in non-blocking mode
2009.02.24 13:34:42 LOG7[3752:216]: TCP_NODELAY option set on local socket
2009.02.24 13:34:42 LOG5[3752:216]: smtp accepted connection from 127.0.0.1:3067
2009.02.24 13:34:42 LOG7[3752:216]: FD 288 in non-blocking mode
2009.02.24 13:34:42 LOG7[3752:216]: smtp connecting 209.85.201.109:465
2009.02.24 13:34:42 LOG7[3752:216]: connect_wait: waiting 10 seconds
2009.02.24 13:34:42 LOG7[3752:216]: connect_wait: connected
2009.02.24 13:34:42 LOG5[3752:216]: smtp connected remote server from 192.168.1.100:3068
2009.02.24 13:34:42 LOG7[3752:216]: Remote FD=288 initialized
2009.02.24 13:34:42 LOG7[3752:216]: TCP_NODELAY option set on remote socket
2009.02.24 13:34:42 LOG7[3752:216]: SSL state (connect): before/connect initialization
2009.02.24 13:34:42 LOG7[3752:216]: SSL state (connect): SSLv3 write client hello A
2009.02.24 13:34:42 LOG7[3752:216]: SSL state (connect): SSLv3 read server hello A
2009.02.24 13:34:42 LOG7[3752:216]: SSL state (connect): SSLv3 read server certificate A
2009.02.24 13:34:42 LOG7[3752:216]: SSL state (connect): SSLv3 read server done A
2009.02.24 13:34:42 LOG7[3752:216]: SSL state (connect): SSLv3 write client key exchange A
2009.02.24 13:34:42 LOG7[3752:216]: SSL state (connect): SSLv3 write change cipher spec A
2009.02.24 13:34:42 LOG7[3752:216]: SSL state (connect): SSLv3 write finished A
2009.02.24 13:34:42 LOG7[3752:216]: SSL state (connect): SSLv3 flush data
2009.02.24 13:34:42 LOG7[3752:216]: SSL state (connect): SSLv3 read finished A
2009.02.24 13:34:42 LOG7[3752:216]:    2 items in the session cache
2009.02.24 13:34:42 LOG7[3752:216]:    2 client connects (SSL_connect())
2009.02.24 13:34:42 LOG7[3752:216]:    2 client connects that finished
2009.02.24 13:34:42 LOG7[3752:216]:    0 client renegotiations requested
2009.02.24 13:34:42 LOG7[3752:216]:    0 server connects (SSL_accept())
2009.02.24 13:34:42 LOG7[3752:216]:    0 server connects that finished
2009.02.24 13:34:42 LOG7[3752:216]:    0 server renegotiations requested
2009.02.24 13:34:42 LOG7[3752:216]:    0 session cache hits
2009.02.24 13:34:42 LOG7[3752:216]:    0 session cache misses
2009.02.24 13:34:42 LOG7[3752:216]:    0 session cache timeouts
2009.02.24 13:34:42 LOG6[3752:216]: SSL connected: new session negotiated
2009.02.24 13:34:42 LOG6[3752:216]: Negotiated ciphers: RC4-MD5 SSLv3 Kx=RSA Au=RSA Enc=RC4(128) Mac=MD5
2009.02.24 13:34:43 LOG3[3752:216]: readsocket: Connection reset by peer (WSAECONNRESET) (10054)
2009.02.24 13:34:43 LOG5[3752:216]: Connection reset: 63 bytes sent to SSL, 335 bytes sent to socket
2009.02.24 13:34:43 LOG7[3752:216]: smtp finished (1 left)
2009.02.24 13:35:43 LOG7[3752:376]: SSL socket closed on SSL_read
2009.02.24 13:35:43 LOG7[3752:376]: Socket write shutdown
2009.02.24 13:35:43 LOG5[3752:376]: Connection closed: 48 bytes sent to SSL, 131 bytes sent to socket
2009.02.24 13:35:43 LOG7[3752:376]: pop finished (0 left)
 

Richard Brust
rbrDataSolutions/ACT! Certified Consulting
http://www.rbrDataSolutions.com
916/769-9411