I am running a win32 based IRC server and I wanted to add SSL to it. I have stunnel up and running. I have the necessary dlls installed. And I have found various help pages on creating the config file. And lastly my irc client is capable of connecting to SSL based servers.

so here is my config file: <---- beging ------>

RNDfile = C:\stunnel-prnd.txt RNDoverwrite = yes

debug = 7 output = C:\stunnel.log

[irc] accept = 66.98.154.87:994 connect = 127.0.0.1:994

<---- ending ----->

And here is the log outup to help figure out what is wrong as well.

<---- log -----> 2005.06.27 21:38:46 LOG5[2364:4084]: stunnel 4.04 on x86-pc-mingw32-gnu WIN32 with OpenSSL 0.9.7c 30 Sep 2003 2005.06.27 21:38:46 LOG7[2364:3120]: RAND_status claims sufficient entropy for the PRNG 2005.06.27 21:38:46 LOG6[2364:3120]: PRNG seeded successfully 2005.06.27 21:38:46 LOG7[2364:3120]: Certificate: stunnel.pem 2005.06.27 21:38:46 LOG7[2364:3120]: Key file: stunnel.pem 2005.06.27 21:38:46 LOG5[2364:3120]: WIN32 platform: 30000 clients allowed 2005.06.27 21:38:46 LOG7[2364:3120]: FD 132 in non-blocking mode 2005.06.27 21:38:46 LOG7[2364:3120]: SO_REUSEADDR option set on accept socket 2005.06.27 21:38:46 LOG7[2364:3120]: irc bound to 66.98.154.87:994 2005.06.27 21:39:43 LOG7[2364:3120]: irc accepted FD=144 from 12.216.55.121:1583 2005.06.27 21:39:43 LOG7[2364:3120]: FD 144 in non-blocking mode 2005.06.27 21:39:43 LOG7[2364:396]: irc started 2005.06.27 21:39:43 LOG5[2364:396]: irc connected from 12.216.55.121:1583 2005.06.27 21:39:43 LOG7[2364:396]: SSL state (accept): before/accept initialization 2005.06.27 21:39:43 LOG7[2364:396]: waitforsocket: FD=144, DIR=read 2005.06.27 21:39:43 LOG7[2364:396]: waitforsocket: ok 2005.06.27 21:39:43 LOG7[2364:396]: SSL state (accept): SSLv3 read client hello A 2005.06.27 21:39:43 LOG7[2364:396]: SSL state (accept): SSLv3 write server hello A 2005.06.27 21:39:43 LOG7[2364:396]: SSL state (accept): SSLv3 write certificate A 2005.06.27 21:39:43 LOG7[2364:396]: SSL state (accept): SSLv3 write server done A 2005.06.27 21:39:43 LOG7[2364:396]: SSL state (accept): SSLv3 flush data 2005.06.27 21:39:43 LOG7[2364:396]: waitforsocket: FD=144, DIR=read 2005.06.27 21:39:43 LOG7[2364:396]: waitforsocket: ok 2005.06.27 21:39:43 LOG7[2364:396]: SSL state (accept): SSLv3 read client key exchange A 2005.06.27 21:39:43 LOG7[2364:396]: SSL state (accept): SSLv3 read finished A 2005.06.27 21:39:43 LOG7[2364:396]: SSL state (accept): SSLv3 write change cipher spec A 2005.06.27 21:39:43 LOG7[2364:396]: SSL state (accept): SSLv3 write finished A 2005.06.27 21:39:43 LOG7[2364:396]: SSL state (accept): SSLv3 flush data 2005.06.27 21:39:43 LOG7[2364:396]: 1 items in the session cache 2005.06.27 21:39:43 LOG7[2364:396]: 0 client connects (SSL_connect()) 2005.06.27 21:39:43 LOG7[2364:396]: 0 client connects that finished 2005.06.27 21:39:43 LOG7[2364:396]: 0 client renegotiatations requested 2005.06.27 21:39:43 LOG7[2364:396]: 1 server connects (SSL_accept()) 2005.06.27 21:39:43 LOG7[2364:396]: 1 server connects that finished 2005.06.27 21:39:43 LOG7[2364:396]: 0 server renegotiatiations requested 2005.06.27 21:39:43 LOG7[2364:396]: 0 session cache hits 2005.06.27 21:39:43 LOG7[2364:396]: 0 session cache misses 2005.06.27 21:39:43 LOG7[2364:396]: 0 session cache timeouts 2005.06.27 21:39:43 LOG6[2364:396]: Negotiated ciphers: AES256-SHA SSLv3 Kx=RSA Au=RSA Enc=AES(256) Mac=SHA1 2005.06.27 21:39:43 LOG7[2364:396]: FD 164 in non-blocking mode 2005.06.27 21:39:43 LOG7[2364:396]: irc connecting 127.0.0.1:994 2005.06.27 21:39:43 LOG7[2364:396]: remote connect #1: EWOULDBLOCK: retrying 2005.06.27 21:39:43 LOG7[2364:396]: waitforsocket: FD=164, DIR=write 2005.06.27 21:44:43 LOG7[2364:396]: waitforsocket: timeout 2005.06.27 21:44:43 LOG3[2364:396]: Failed to initialize remote connection 2005.06.27 21:44:43 LOG7[2364:396]: irc finished (0 left) 2005.06.27 21:44:47 LOG7[2364:3120]: irc accepted FD=180 from 12.216.55.121:1639 2005.06.27 21:44:47 LOG7[2364:3120]: FD 180 in non-blocking mode 2005.06.27 21:44:47 LOG7[2364:768]: irc started 2005.06.27 21:44:47 LOG5[2364:768]: irc connected from 12.216.55.121:1639 2005.06.27 21:44:47 LOG7[2364:768]: SSL state (accept): before/accept initialization 2005.06.27 21:44:47 LOG7[2364:768]: waitforsocket: FD=180, DIR=read 2005.06.27 21:44:47 LOG7[2364:768]: waitforsocket: ok 2005.06.27 21:44:47 LOG7[2364:768]: SSL state (accept): SSLv3 read client hello A 2005.06.27 21:44:47 LOG7[2364:768]: SSL state (accept): SSLv3 write server hello A 2005.06.27 21:44:47 LOG7[2364:768]: SSL state (accept): SSLv3 write certificate A 2005.06.27 21:44:47 LOG7[2364:768]: SSL state (accept): SSLv3 write server done A 2005.06.27 21:44:47 LOG7[2364:768]: SSL state (accept): SSLv3 flush data 2005.06.27 21:44:47 LOG7[2364:768]: waitforsocket: FD=180, DIR=read 2005.06.27 21:44:47 LOG7[2364:768]: waitforsocket: ok 2005.06.27 21:44:47 LOG7[2364:768]: SSL state (accept): SSLv3 read client key exchange A 2005.06.27 21:44:47 LOG7[2364:768]: SSL state (accept): SSLv3 read finished A 2005.06.27 21:44:47 LOG7[2364:768]: SSL state (accept): SSLv3 write change cipher spec A 2005.06.27 21:44:47 LOG7[2364:768]: SSL state (accept): SSLv3 write finished A 2005.06.27 21:44:47 LOG7[2364:768]: SSL state (accept): SSLv3 flush data 2005.06.27 21:44:47 LOG7[2364:768]: 2 items in the session cache 2005.06.27 21:44:47 LOG7[2364:768]: 0 client connects (SSL_connect()) 2005.06.27 21:44:47 LOG7[2364:768]: 0 client connects that finished 2005.06.27 21:44:47 LOG7[2364:768]: 0 client renegotiatations requested 2005.06.27 21:44:47 LOG7[2364:768]: 2 server connects (SSL_accept()) 2005.06.27 21:44:47 LOG7[2364:768]: 2 server connects that finished 2005.06.27 21:44:47 LOG7[2364:768]: 0 server renegotiatiations requested 2005.06.27 21:44:47 LOG7[2364:768]: 0 session cache hits 2005.06.27 21:44:47 LOG7[2364:768]: 0 session cache misses 2005.06.27 21:44:47 LOG7[2364:768]: 0 session cache timeouts 2005.06.27 21:44:47 LOG6[2364:768]: Negotiated ciphers: AES256-SHA SSLv3 Kx=RSA Au=RSA Enc=AES(256) Mac=SHA1 2005.06.27 21:44:47 LOG7[2364:768]: FD 148 in non-blocking mode 2005.06.27 21:44:47 LOG7[2364:768]: irc connecting 127.0.0.1:994 2005.06.27 21:44:47 LOG7[2364:768]: remote connect #1: EWOULDBLOCK: retrying 2005.06.27 21:44:47 LOG7[2364:768]: waitforsocket: FD=148, DIR=write 2005.06.27 21:49:47 LOG7[2364:768]: waitforsocket: timeout 2005.06.27 21:49:47 LOG3[2364:768]: Failed to initialize remote connection 2005.06.27 21:49:47 LOG7[2364:768]: irc finished (0 left) 2005.06.27 21:49:51 LOG7[2364:3120]: irc accepted FD=168 from 12.216.55.121:1689 2005.06.27 21:49:51 LOG7[2364:3120]: FD 168 in non-blocking mode 2005.06.27 21:49:51 LOG7[2364:2508]: irc started 2005.06.27 21:49:51 LOG5[2364:2508]: irc connected from 12.216.55.121:1689 2005.06.27 21:49:51 LOG7[2364:2508]: SSL state (accept): before/accept initialization 2005.06.27 21:49:51 LOG7[2364:2508]: waitforsocket: FD=168, DIR=read 2005.06.27 21:49:51 LOG7[2364:2508]: waitforsocket: ok 2005.06.27 21:49:51 LOG7[2364:2508]: SSL state (accept): SSLv3 read client hello A 2005.06.27 21:49:51 LOG7[2364:2508]: SSL state (accept): SSLv3 write server hello A 2005.06.27 21:49:51 LOG7[2364:2508]: SSL state (accept): SSLv3 write certificate A 2005.06.27 21:49:51 LOG7[2364:2508]: SSL state (accept): SSLv3 write server done A 2005.06.27 21:49:51 LOG7[2364:2508]: SSL state (accept): SSLv3 flush data 2005.06.27 21:49:51 LOG7[2364:2508]: waitforsocket: FD=168, DIR=read 2005.06.27 21:49:51 LOG7[2364:2508]: waitforsocket: ok 2005.06.27 21:49:51 LOG7[2364:2508]: SSL state (accept): SSLv3 read client key exchange A 2005.06.27 21:49:51 LOG7[2364:2508]: SSL state (accept): SSLv3 read finished A 2005.06.27 21:49:51 LOG7[2364:2508]: SSL state (accept): SSLv3 write change cipher spec A 2005.06.27 21:49:51 LOG7[2364:2508]: SSL state (accept): SSLv3 write finished A 2005.06.27 21:49:51 LOG7[2364:2508]: SSL state (accept): SSLv3 flush data 2005.06.27 21:49:51 LOG7[2364:2508]: 3 items in the session cache 2005.06.27 21:49:51 LOG7[2364:2508]: 0 client connects (SSL_connect()) 2005.06.27 21:49:51 LOG7[2364:2508]: 0 client connects that finished 2005.06.27 21:49:51 LOG7[2364:2508]: 0 client renegotiatations requested 2005.06.27 21:49:51 LOG7[2364:2508]: 3 server connects (SSL_accept()) 2005.06.27 21:49:51 LOG7[2364:2508]: 3 server connects that finished 2005.06.27 21:49:51 LOG7[2364:2508]: 0 server renegotiatiations requested 2005.06.27 21:49:51 LOG7[2364:2508]: 0 session cache hits 2005.06.27 21:49:51 LOG7[2364:2508]: 0 session cache misses 2005.06.27 21:49:51 LOG7[2364:2508]: 0 session cache timeouts 2005.06.27 21:49:51 LOG6[2364:2508]: Negotiated ciphers: AES256-SHA SSLv3 Kx=RSA Au=RSA Enc=AES(256) Mac=SHA1 2005.06.27 21:49:51 LOG7[2364:2508]: FD 156 in non-blocking mode 2005.06.27 21:49:51 LOG7[2364:2508]: irc connecting 127.0.0.1:994 2005.06.27 21:49:51 LOG7[2364:2508]: remote connect #1: EWOULDBLOCK: retrying 2005.06.27 21:49:51 LOG7[2364:2508]: waitforsocket: FD=156, DIR=write 2005.06.27 21:54:51 LOG7[2364:2508]: waitforsocket: timeout 2005.06.27 21:54:51 LOG3[2364:2508]: Failed to initialize remote connection 2005.06.27 21:54:51 LOG7[2364:2508]: irc finished (0 left) 2005.06.27 21:54:55 LOG7[2364:3120]: irc accepted FD=164 from 12.216.55.121:1747 2005.06.27 21:54:55 LOG7[2364:3120]: FD 164 in non-blocking mode 2005.06.27 21:54:55 LOG7[2364:460]: irc started 2005.06.27 21:54:55 LOG5[2364:460]: irc connected from 12.216.55.121:1747 2005.06.27 21:54:55 LOG7[2364:460]: SSL state (accept): before/accept initialization 2005.06.27 21:54:55 LOG7[2364:460]: SSL state (accept): SSLv3 read client hello A 2005.06.27 21:54:55 LOG7[2364:460]: SSL state (accept): SSLv3 write server hello A 2005.06.27 21:54:55 LOG7[2364:460]: SSL state (accept): SSLv3 write certificate A 2005.06.27 21:54:55 LOG7[2364:460]: SSL state (accept): SSLv3 write server done A 2005.06.27 21:54:55 LOG7[2364:460]: SSL state (accept): SSLv3 flush data 2005.06.27 21:54:55 LOG7[2364:460]: waitforsocket: FD=164, DIR=read 2005.06.27 21:54:55 LOG7[2364:460]: waitforsocket: ok 2005.06.27 21:54:55 LOG7[2364:460]: SSL state (accept): SSLv3 read client key exchange A 2005.06.27 21:54:55 LOG7[2364:460]: SSL state (accept): SSLv3 read finished A 2005.06.27 21:54:55 LOG7[2364:460]: SSL state (accept): SSLv3 write change cipher spec A 2005.06.27 21:54:55 LOG7[2364:460]: SSL state (accept): SSLv3 write finished A 2005.06.27 21:54:55 LOG7[2364:460]: SSL state (accept): SSLv3 flush data 2005.06.27 21:54:55 LOG7[2364:460]: 4 items in the session cache 2005.06.27 21:54:55 LOG7[2364:460]: 0 client connects (SSL_connect()) 2005.06.27 21:54:55 LOG7[2364:460]: 0 client connects that finished 2005.06.27 21:54:55 LOG7[2364:460]: 0 client renegotiatations requested 2005.06.27 21:54:55 LOG7[2364:460]: 4 server connects (SSL_accept()) 2005.06.27 21:54:55 LOG7[2364:460]: 4 server connects that finished 2005.06.27 21:54:55 LOG7[2364:460]: 0 server renegotiatiations requested 2005.06.27 21:54:55 LOG7[2364:460]: 0 session cache hits 2005.06.27 21:54:55 LOG7[2364:460]: 0 session cache misses 2005.06.27 21:54:55 LOG7[2364:460]: 0 session cache timeouts 2005.06.27 21:54:55 LOG6[2364:460]: Negotiated ciphers: AES256-SHA SSLv3 Kx=RSA Au=RSA Enc=AES(256) Mac=SHA1 2005.06.27 21:54:55 LOG7[2364:460]: FD 144 in non-blocking mode 2005.06.27 21:54:55 LOG7[2364:460]: irc connecting 127.0.0.1:994 2005.06.27 21:54:55 LOG7[2364:460]: remote connect #1: EWOULDBLOCK: retrying 2005.06.27 21:54:55 LOG7[2364:460]: waitforsocket: FD=144, DIR=write 2005.06.27 21:59:55 LOG7[2364:460]: waitforsocket: timeout 2005.06.27 21:59:55 LOG3[2364:460]: Failed to initialize remote connection 2005.06.27 21:59:55 LOG7[2364:460]: irc finished (0 left) 2005.06.27 21:59:59 LOG7[2364:3120]: irc accepted FD=148 from 12.216.55.121:1813 2005.06.27 21:59:59 LOG7[2364:3120]: FD 148 in non-blocking mode 2005.06.27 21:59:59 LOG7[2364:2240]: irc started 2005.06.27 21:59:59 LOG5[2364:2240]: irc connected from 12.216.55.121:1813 2005.06.27 21:59:59 LOG7[2364:2240]: SSL state (accept): before/accept initialization 2005.06.27 21:59:59 LOG7[2364:2240]: waitforsocket: FD=148, DIR=read 2005.06.27 21:59:59 LOG7[2364:2240]: waitforsocket: ok 2005.06.27 21:59:59 LOG7[2364:2240]: SSL state (accept): SSLv3 read client hello A 2005.06.27 21:59:59 LOG7[2364:2240]: SSL state (accept): SSLv3 write server hello A 2005.06.27 21:59:59 LOG7[2364:2240]: SSL state (accept): SSLv3 write certificate A 2005.06.27 21:59:59 LOG7[2364:2240]: SSL state (accept): SSLv3 write server done A 2005.06.27 21:59:59 LOG7[2364:2240]: SSL state (accept): SSLv3 flush data 2005.06.27 21:59:59 LOG7[2364:2240]: waitforsocket: FD=148, DIR=read 2005.06.27 21:59:59 LOG7[2364:2240]: waitforsocket: ok 2005.06.27 21:59:59 LOG7[2364:2240]: SSL state (accept): SSLv3 read client key exchange A 2005.06.27 21:59:59 LOG7[2364:2240]: SSL state (accept): SSLv3 read finished A 2005.06.27 21:59:59 LOG7[2364:2240]: SSL state (accept): SSLv3 write change cipher spec A 2005.06.27 21:59:59 LOG7[2364:2240]: SSL state (accept): SSLv3 write finished A 2005.06.27 21:59:59 LOG7[2364:2240]: SSL state (accept): SSLv3 flush data 2005.06.27 21:59:59 LOG7[2364:2240]: 5 items in the session cache 2005.06.27 21:59:59 LOG7[2364:2240]: 0 client connects (SSL_connect()) 2005.06.27 21:59:59 LOG7[2364:2240]: 0 client connects that finished 2005.06.27 21:59:59 LOG7[2364:2240]: 0 client renegotiatations requested 2005.06.27 21:59:59 LOG7[2364:2240]: 5 server connects (SSL_accept()) 2005.06.27 21:59:59 LOG7[2364:2240]: 5 server connects that finished 2005.06.27 21:59:59 LOG7[2364:2240]: 0 server renegotiatiations requested 2005.06.27 21:59:59 LOG7[2364:2240]: 0 session cache hits 2005.06.27 21:59:59 LOG7[2364:2240]: 0 session cache misses 2005.06.27 21:59:59 LOG7[2364:2240]: 0 session cache timeouts 2005.06.27 21:59:59 LOG6[2364:2240]: Negotiated ciphers: AES256-SHA SSLv3 Kx=RSA Au=RSA Enc=AES(256) Mac=SHA1 2005.06.27 21:59:59 LOG7[2364:2240]: FD 180 in non-blocking mode 2005.06.27 21:59:59 LOG7[2364:2240]: irc connecting 127.0.0.1:994 2005.06.27 21:59:59 LOG7[2364:2240]: remote connect #1: EWOULDBLOCK: retrying 2005.06.27 21:59:59 LOG7[2364:2240]: waitforsocket: FD=180, DIR=write <--- end log ----->

Any help that gets this working would be great. Thanks