I'v used FreeBsd with stunnel without problem, so I'm a little stumped that it doesn't work properly on darwin for Mac. I recall that it might get hung up in the ssl certificates, but I can't find where to look and openssl -connect works perfectly.

Any help, appreciated.

Symptom: The stunnel is running in debug mode, the client makes a connection to stunnel, stunnel reports the connection stunnel does not attempt to connect to the host (the connect string) No messages suggest it is trying, no network logic show it is connecting.

(Since I am using it for email, I can not copy and paste from the orginal to send this email)

openssl connects fine to the server and get the correct results

Any ideas how/ where to find out what is wrong with the Mac.

Thanks

stunnel 4.20 on i686-apple-darwin8.10.1 with OpenSSL 0.9.7l 28 Sep 2006 Threading:PTHREAD SSL:ENGINE Sockets:SELECT,IPv4 Auth:LIBWRAP

Global options debug = 5 pid = /opt/local/var/run/stunnel/stunnel.pid RNDbytes = 64 RNDfile = /dev/urandom RNDoverwrite = yes

Service-level options cert = /opt/local/etc/stunnel/stunnel.pem ciphers = ALL:!ADH:+RC4:@STRENGTH key = /opt/local/etc/stunnel/stunnel.pem session = 300 seconds sslVersion = SSLv3 for client, all for server TIMEOUTbusy = 300 seconds TIMEOUTclose = 60 seconds TIMEOUTconnect = 10 seconds TIMEOUTidle = 43200 seconds verify = none

2007.08.26 20:28:51 LOG7[207:2684407808]: RAND_status claims sufficient entropy for the PRNG 2007.08.26 20:28:51 LOG7[207:2684407808]: PRNG seeded successfully 2007.08.26 20:28:51 LOG7[207:2684407808]: Certificate: /opt/local/etc/stunnel/stunnel.pem 2007.08.26 20:28:51 LOG7[207:2684407808]: Certificate loaded 2007.08.26 20:28:51 LOG7[207:2684407808]: Key file: /opt/local/etc/stunnel/stunnel.pem 2007.08.26 20:28:51 LOG7[207:2684407808]: Private key loaded 2007.08.26 20:28:51 LOG7[207:2684407808]: SSL context initialized for service pop3s 2007.08.26 20:28:51 LOG7[207:2684407808]: Certificate: /opt/local/etc/stunnel/stunnel.pem 2007.08.26 20:28:51 LOG7[207:2684407808]: Certificate loaded 2007.08.26 20:28:51 LOG7[207:2684407808]: Key file: /opt/local/etc/stunnel/stunnel.pem 2007.08.26 20:28:51 LOG7[207:2684407808]: Private key loaded 2007.08.26 20:28:51 LOG7[207:2684407808]: SSL context initialized for service smtps 2007.08.26 20:28:51 LOG5[207:2684407808]: stunnel 4.20 on i686-apple-darwin8.10.1 with OpenSSL 0.9.7l 28 Sep 2006 2007.08.26 20:28:51 LOG5[207:2684407808]: Threading:PTHREAD SSL:ENGINE Sockets:SELECT,IPv4 Auth:LIBWRAP 2007.08.26 20:28:51 LOG6[207:2684407808]: file ulimit = 256 (can be changed with 'ulimit -n') 2007.08.26 20:28:51 LOG6[207:2684407808]: FD_SETSIZE = 1024 (some systems allow to increase this value) 2007.08.26 20:28:51 LOG5[207:2684407808]: 125 clients allowed 2007.08.26 20:28:51 LOG7[207:2684407808]: FD 4 in non-blocking mode 2007.08.26 20:28:51 LOG7[207:2684407808]: FD 6 in non-blocking mode 2007.08.26 20:28:51 LOG7[207:2684407808]: FD 7 in non-blocking mode 2007.08.26 20:28:51 LOG7[207:2684407808]: SO_REUSEADDR option set on accept socket 2007.08.26 20:28:51 LOG7[207:2684407808]: pop3s bound to 0.0.0.0:995 2007.08.26 20:28:51 LOG7[207:2684407808]: FD 8 in non-blocking mode 2007.08.26 20:28:51 LOG7[207:2684407808]: SO_REUSEADDR option set on accept socket 2007.08.26 20:28:51 LOG7[207:2684407808]: smtps bound to 0.0.0.0:5526 2007.08.26 20:28:51 LOG7[207:2684407808]: Created pid file /tmp/stunnel.pid 2007.08.26 20:29:04 LOG7[207:2684407808]: pop3s accepted FD=9 from 127.0.0.1:49162 2007.08.26 20:29:04 LOG7[207:25185792]: pop3s started 2007.08.26 20:29:04 LOG7[207:25185792]: FD 9 in non-blocking mode 2007.08.26 20:29:04 LOG7[207:25185792]: FD 10 in non-blocking mode 2007.08.26 20:29:04 LOG7[207:25185792]: FD 11 in non-blocking mode 2007.08.26 20:29:04 LOG7[207:25185792]: Connection from 127.0.0.1:49162 permitted by libwrap 2007.08.26 20:29:04 LOG5[207:25185792]: pop3s accepted connection from 127.0.0.1:49162 2007.08.26 20:29:04 LOG7[207:25185792]: SSL state (accept): before/accept initialization 2007.08.26 20:29:04 LOG7[207:2684407808]: Cleaning up the signal pipe 2007.08.26 20:29:04 LOG6[207:2684407808]: Child process 212 finished with code 0

<<-- at this point I have done nothing but connect to the stunnel, so I don;t know why it should finished with code 0 yet, and has not closed the connect on the other side.