I see that you have client = yes in the config file. When client = yes is set outside the service block, it becomes a global setting that tells all the services that it should tunnel that they are clients and not servers. If you specify the client = yes within a service eg. [pop3s] client = yes accept = 995 connect = 110 then stunnel knows that the specified service alone is a client. What I recommend is that you disable the client = yes in the global area and change you config file to something like this: I have removed the comments to shorten the config for explanation: socket = l:TCP_NODELAY=1 socket = r:TCP_NODELAY=1 CRLpath = crls CRLfile = certnew.pem debug = 7 output = stunnel.log ;client = yes [https] accept = 443 connect = 192.168.0.5:443 TIMEOUTclose = 0 Try using this as your config and see if it works or not. Cheers Craig From: Dan Vespa [mailto:dan@sideshow.sytes.net] Sent: 19 November 2007 05:07 PM To: Craig Retief Subject: RE: [stunnel-users] Stunnel and Outlook Web Access Problems Craig, Here it is.... ; Sample stunnel configuration file by Michal Trojnara 2002-2006 ; Some options used here may not be adequate for your particular configuration ; Certificate/key is needed in server mode and optional in client mode ; The default certificate is provided only for testing and should not ; be used in a production environment ;cert = stunnel.pem ;key = stunnel.pem ; Some performance tunings socket = l:TCP_NODELAY=1 socket = r:TCP_NODELAY=1 ; Workaround for Eudora bug ;options = DONT_INSERT_EMPTY_FRAGMENTS ; Authentication stuff ;verify = 2 ; Don't forget to c_rehash CApath ;CApath = crls ; It's often easier to use CAfile ;CAfile = certnew.pem ; Don't forget to c_rehash CRLpath CRLpath = crls ; Alternatively you can use CRLfile CRLfile = certnew.pem ; Some debugging stuff useful for troubleshooting debug = 7 output = stunnel.log ; Use it for client mode client = yes ; Service-level configuration ;[pop3s] ;accept = 995 ;connect = 110 ;[imaps] ;accept = 993 ;connect = 143 ;[ssmtp] ;accept = 465 ;connect = 25 [https] accept = 443 connect = 192.168.0.5:443 TIMEOUTclose = 0 ; vim:ft=dosini _____ From: Craig Retief Sent: Mon 19/11/2007 9:54 AM To: 'Dan Vespa' Cc: stunnel-users@mirt.net Subject: RE: [stunnel-users] Stunnel and Outlook Web Access Problems Please Post your stunnel configs. Makes life easier. Cheers Craig From: Dan Vespa [mailto:dan@sideshow.sytes.net] Sent: 19 November 2007 03:35 PM To: Craig Subject: RE: [stunnel-users] Stunnel and Outlook Web Access Problems Craig, I set the debug level higher and this is what my log outputs.... 2007.11.19 08:25:54 LOG7[1596:2656]: RAND_status claims sufficient entropy for the PRNG 2007.11.19 08:25:54 LOG7[1596:2656]: PRNG seeded successfully 2007.11.19 08:25:54 LOG7[1596:2656]: SSL context initialized for service https 2007.11.19 08:25:54 LOG5[1596:2656]: stunnel 4.21 on x86-pc-mingw32-gnu with OpenSSL 0.9.8g 19 Oct 2007 2007.11.19 08:25:54 LOG5[1596:2656]: Threading:WIN32 SSL:ENGINE Sockets:SELECT,IPv6 2007.11.19 08:25:54 LOG5[1596:3012]: No limit detected for the number of clients 2007.11.19 08:25:54 LOG7[1596:3012]: FD 188 in non-blocking mode 2007.11.19 08:25:54 LOG7[1596:3012]: SO_REUSEADDR option set on accept socket 2007.11.19 08:25:54 LOG7[1596:3012]: https bound to 0.0.0.0:443 2007.11.19 08:26:32 LOG7[1596:3012]: https accepted FD=236 from 127.0.0.1:1409 2007.11.19 08:26:32 LOG7[1596:3012]: Creating a new thread 2007.11.19 08:26:32 LOG7[1596:3012]: New thread created 2007.11.19 08:26:32 LOG7[1596:2576]: https started 2007.11.19 08:26:32 LOG7[1596:2576]: FD 236 in non-blocking mode 2007.11.19 08:26:32 LOG7[1596:2576]: TCP_NODELAY option set on local socket 2007.11.19 08:26:32 LOG5[1596:2576]: https accepted connection from 127.0.0.1:1409 2007.11.19 08:26:32 LOG7[1596:2576]: FD 260 in non-blocking mode 2007.11.19 08:26:32 LOG7[1596:2576]: https connecting 192.168.0.5:443 2007.11.19 08:26:32 LOG7[1596:2576]: connect_wait: waiting 10 seconds 2007.11.19 08:26:32 LOG7[1596:2576]: connect_wait: connected 2007.11.19 08:26:32 LOG5[1596:2576]: https connected remote server from 192.168.0.24:1410 2007.11.19 08:26:32 LOG7[1596:2576]: Remote FD=260 initialized 2007.11.19 08:26:32 LOG7[1596:2576]: TCP_NODELAY option set on remote socket 2007.11.19 08:26:32 LOG7[1596:2576]: SSL state (connect): before/connect initialization 2007.11.19 08:26:32 LOG7[1596:2576]: SSL state (connect): SSLv3 write client hello A 2007.11.19 08:26:32 LOG7[1596:2576]: SSL state (connect): SSLv3 read server hello A 2007.11.19 08:26:32 LOG7[1596:2576]: SSL state (connect): SSLv3 read server certificate A 2007.11.19 08:26:32 LOG7[1596:2576]: SSL state (connect): SSLv3 read server done A 2007.11.19 08:26:32 LOG7[1596:2576]: SSL state (connect): SSLv3 write client key exchange A 2007.11.19 08:26:32 LOG7[1596:2576]: SSL state (connect): SSLv3 write change cipher spec A 2007.11.19 08:26:32 LOG7[1596:2576]: SSL state (connect): SSLv3 write finished A 2007.11.19 08:26:32 LOG7[1596:2576]: SSL state (connect): SSLv3 flush data 2007.11.19 08:26:32 LOG7[1596:2576]: SSL state (connect): SSLv3 read finished A 2007.11.19 08:26:32 LOG7[1596:2576]: 1 items in the session cache 2007.11.19 08:26:32 LOG7[1596:2576]: 1 client connects (SSL_connect()) 2007.11.19 08:26:32 LOG7[1596:2576]: 1 client connects that finished 2007.11.19 08:26:32 LOG7[1596:2576]: 0 client renegotiations requested 2007.11.19 08:26:32 LOG7[1596:2576]: 0 server connects (SSL_accept()) 2007.11.19 08:26:32 LOG7[1596:2576]: 0 server connects that finished 2007.11.19 08:26:32 LOG7[1596:2576]: 0 server renegotiations requested 2007.11.19 08:26:32 LOG7[1596:2576]: 0 session cache hits 2007.11.19 08:26:32 LOG7[1596:2576]: 0 session cache misses 2007.11.19 08:26:32 LOG7[1596:2576]: 0 session cache timeouts 2007.11.19 08:26:32 LOG6[1596:2576]: SSL connected: new session negotiated 2007.11.19 08:26:32 LOG6[1596:2576]: Negotiated ciphers: RC4-MD5 SSLv3 Kx=RSA Au=RSA Enc=RC4(128) Mac=MD5 2007.11.19 08:26:53 LOG7[1596:3012]: https accepted FD=288 from 127.0.0.1:1411 2007.11.19 08:26:53 LOG7[1596:3012]: Creating a new thread 2007.11.19 08:26:53 LOG7[1596:3012]: New thread created 2007.11.19 08:26:53 LOG7[1596:1060]: https started 2007.11.19 08:26:53 LOG7[1596:1060]: FD 288 in non-blocking mode 2007.11.19 08:26:53 LOG7[1596:1060]: TCP_NODELAY option set on local socket 2007.11.19 08:26:53 LOG5[1596:1060]: https accepted connection from 127.0.0.1:1411 2007.11.19 08:26:53 LOG7[1596:1060]: FD 312 in non-blocking mode 2007.11.19 08:26:53 LOG7[1596:1060]: https connecting 192.168.0.5:443 2007.11.19 08:26:53 LOG7[1596:1060]: connect_wait: waiting 10 seconds 2007.11.19 08:26:53 LOG7[1596:1060]: connect_wait: connected 2007.11.19 08:26:53 LOG5[1596:1060]: https connected remote server from 192.168.0.24:1412 2007.11.19 08:26:53 LOG7[1596:1060]: Remote FD=312 initialized 2007.11.19 08:26:53 LOG7[1596:1060]: TCP_NODELAY option set on remote socket 2007.11.19 08:26:53 LOG7[1596:1060]: SSL state (connect): before/connect initialization 2007.11.19 08:26:53 LOG7[1596:1060]: SSL state (connect): SSLv3 write client hello A 2007.11.19 08:26:53 LOG7[1596:1060]: SSL state (connect): SSLv3 read server hello A 2007.11.19 08:26:53 LOG7[1596:1060]: SSL state (connect): SSLv3 read finished A 2007.11.19 08:26:53 LOG7[1596:1060]: SSL state (connect): SSLv3 write change cipher spec A 2007.11.19 08:26:53 LOG7[1596:1060]: SSL state (connect): SSLv3 write finished A 2007.11.19 08:26:53 LOG7[1596:1060]: SSL state (connect): SSLv3 flush data 2007.11.19 08:26:53 LOG7[1596:1060]: 1 items in the session cache 2007.11.19 08:26:53 LOG7[1596:1060]: 2 client connects (SSL_connect()) 2007.11.19 08:26:53 LOG7[1596:1060]: 2 client connects that finished 2007.11.19 08:26:53 LOG7[1596:1060]: 0 client renegotiations requested 2007.11.19 08:26:53 LOG7[1596:1060]: 0 server connects (SSL_accept()) 2007.11.19 08:26:53 LOG7[1596:1060]: 0 server connects that finished 2007.11.19 08:26:53 LOG7[1596:1060]: 0 server renegotiations requested 2007.11.19 08:26:53 LOG7[1596:1060]: 1 session cache hits 2007.11.19 08:26:53 LOG7[1596:1060]: 0 session cache misses 2007.11.19 08:26:53 LOG7[1596:1060]: 0 session cache timeouts 2007.11.19 08:26:53 LOG6[1596:1060]: SSL connected: previous session reused 2007.11.19 08:26:53 LOG7[1596:1060]: SSL socket closed on SSL_read 2007.11.19 08:26:53 LOG7[1596:1060]: Socket write shutdown 2007.11.19 08:26:53 LOG5[1596:1060]: Connection closed: 70 bytes sent to SSL, 164 bytes sent to socket 2007.11.19 08:26:53 LOG7[1596:1060]: https finished (1 left) 2007.11.19 08:27:53 LOG3[1596:2576]: readsocket: Connection reset by peer (WSAECONNRESET) (10054) 2007.11.19 08:27:53 LOG5[1596:2576]: Connection reset: 1102 bytes sent to SSL, 1241 bytes sent to socket 2007.11.19 08:27:53 LOG7[1596:2576]: https finished (0 left) Does this make any sense to you???? Dan _____ From: Craig Sent: Mon 19/11/2007 1:34 AM To: stunnel-users@mirt.net Subject: Re: [stunnel-users] Stunnel and Outlook Web Access Problems OWA rewrites the URL when you log in and I have found that it causes problems when doing that with a Stunnel connection. What I think might be happening is that your initial connection says http://server.tld/ then when you log in OWA rewrites the URL to https://server.tld/ What I think is happening is that your stunnel is listening on port 80 and when you log in, OWA changes the listening port in the browser to port 443. Try running the listening server (stunnel server) to listen on port 443 instead of port 80 and see if that fixes the problem. Cheers Craig From: stunnel-users-bounces@mirt.net [mailto:stunnel-users-bounces@mirt.net] On Behalf Of Dan Vespa Sent: 17 November 2007 07:21 PM To: stunnel-users@mirt.net Subject: [stunnel-users] Stunnel and Outlook Web Access Problems I am trying to use the latest version of stunnel to connect to OWA. I set stunnel to listen on port 80 (localhost) and then connect to myserverip on port 443. I get the login screen but can go no further after I Enter my credentials and Click OK. Checking the stunnel log screen it shows that a connect has been made? I don't understand why It won't connect any further?? OWA is on Exchange Server 2003 and I am using Windows XP SP2. I have also updated to Open SSL latest version. Thanks in Advance. Dan