[stunnel-users] Still not working with client certificates

Hello,

I'm hoping that someone can give me a hint of where to look at this issue because I'm totally stuck and have been for a few days. When I attempt to use sTunnel in client mode with client certificates, the SSL seems to negotiate the certs and ciphers and then nothing else happens; the services hang. I'm hoping that someone has some insights about something that I haven't looked at, yet.

My setup:

Server: Windows Server, IIS 7 running SOAP services set for SSL Required, Client Certificate required (transport level client certificate, not SOAP message level).

client: Windows machine, simple web application acting as a test client for the SOAP service.

In between: sTunnel v4.32

Testing Scenario #1 -- Client configured to use client certificates directly against the IIS 7 service instance. This works as expected.

Testing Scenario #2 -- Server configured to not require client certificates, but require SSL. sTunnel configured to listen on local port 8090 and forward to the IIS 7 server. This works as expected.

Testing Scenario #3 -- Server configured to require client certificates. sTunnel configured to use client certificate as issued by a local CA in addition to the setup as before. This does not work, but hangs.

sTunnel.conf:

; 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 = C:\certs\client-cert-for-internal-environments.pem ;key = c:\certs\test_cert.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 = certs ; It's often easier to use CAfile ;CAfile = certs.pem ; Don't forget to c_rehash CRLpath ;CRLpath = crls ; Alternatively you can use CRLfile ;CRLfile = crls.pem ; Some debugging stuff useful for troubleshooting debug = 7 output = c:\temp\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 [http] accept = 8090 ;connect = 10.12.32.164:443 connect = 10.12.32.68:1443 TIMEOUTclose = 0 ; vim:ft=dosini

sTunnel log:

2010.03.24 11:54:31 LOG5[5616:5992]: Reading configuration from file stunnel.conf 2010.03.24 11:54:31 LOG7[5616:5992]: RAND_status claims sufficient entropy for the PRNG 2010.03.24 11:54:31 LOG7[5616:5992]: PRNG seeded successfully 2010.03.24 11:54:31 LOG7[5616:5992]: Certificate: C:\certs\client-cert-for-internal-environments.pem 2010.03.24 11:54:31 LOG7[5616:5992]: Certificate loaded 2010.03.24 11:54:31 LOG7[5616:5992]: Key file: C:\certs\client-cert-for-internal-environments.pem 2010.03.24 11:54:38 LOG7[5616:5992]: Private key loaded 2010.03.24 11:54:38 LOG7[5616:5992]: SSL context initialized for service http 2010.03.24 11:54:38 LOG5[5616:5992]: Configuration successful 2010.03.24 11:54:38 LOG5[5616:5992]: No limit detected for the number of clients 2010.03.24 11:54:38 LOG7[5616:5992]: FD=176 in non-blocking mode 2010.03.24 11:54:38 LOG7[5616:5992]: Option SO_REUSEADDR set on accept socket 2010.03.24 11:54:38 LOG7[5616:5992]: Service http bound to 0.0.0.0:8090 2010.03.24 11:54:38 LOG7[5616:5992]: Service http opened FD=176 2010.03.24 11:54:38 LOG3[5616:5992]: c:\temp\stunnel.log: Input/output error (5) 2010.03.24 11:54:38 LOG3[5616:5992]: Unable to open output file: c:\temp\stunnel.log 2010.03.24 11:54:38 LOG5[5616:5992]: stunnel 4.32 on x86-pc-mingw32-gnu with OpenSSL 0.9.8l 5 Nov 2009 2010.03.24 11:54:38 LOG5[5616:5992]: Threading:WIN32 SSL:ENGINE Sockets:SELECT,IPv6 2010.03.24 11:54:54 LOG7[5616:6192]: Service http accepted FD=436 from 127.0.0.1:56102 2010.03.24 11:54:54 LOG7[5616:6192]: Creating a new thread 2010.03.24 11:54:54 LOG7[5616:6192]: New thread created 2010.03.24 11:54:54 LOG7[5616:6696]: Service http started 2010.03.24 11:54:54 LOG7[5616:6696]: FD=436 in non-blocking mode 2010.03.24 11:54:54 LOG7[5616:6696]: Option TCP_NODELAY set on local socket 2010.03.24 11:54:54 LOG5[5616:6696]: Service http accepted connection from 127.0.0.1:56102 2010.03.24 11:54:54 LOG7[5616:6696]: FD=456 in non-blocking mode 2010.03.24 11:54:54 LOG6[5616:6696]: connect_blocking: connecting 10.12.32.68:1443 2010.03.24 11:54:54 LOG7[5616:6696]: connect_blocking: s_poll_wait 10.12.32.68:1443: waiting 10 seconds 2010.03.24 11:54:54 LOG5[5616:6696]: connect_blocking: connected 10.12.32.68:1443 2010.03.24 11:54:54 LOG5[5616:6696]: Service http connected remote server from 10.12.47.109:56103 2010.03.24 11:54:54 LOG7[5616:6696]: Remote FD=456 initialized 2010.03.24 11:54:54 LOG7[5616:6696]: Option TCP_NODELAY set on remote socket 2010.03.24 11:54:54 LOG7[5616:6696]: SSL state (connect): before/connect initialization 2010.03.24 11:54:54 LOG7[5616:6696]: SSL state (connect): SSLv3 write client hello A 2010.03.24 11:54:54 LOG7[5616:6696]: SSL state (connect): SSLv3 read server hello A 2010.03.24 11:54:54 LOG7[5616:6696]: SSL state (connect): SSLv3 read server certificate A 2010.03.24 11:54:54 LOG7[5616:6696]: SSL state (connect): SSLv3 read server done A 2010.03.24 11:54:54 LOG7[5616:6696]: SSL state (connect): SSLv3 write client key exchange A 2010.03.24 11:54:54 LOG7[5616:6696]: SSL state (connect): SSLv3 write change cipher spec A 2010.03.24 11:54:54 LOG7[5616:6696]: SSL state (connect): SSLv3 write finished A 2010.03.24 11:54:54 LOG7[5616:6696]: SSL state (connect): SSLv3 flush data 2010.03.24 11:54:54 LOG7[5616:6696]: SSL state (connect): SSLv3 read finished A 2010.03.24 11:54:54 LOG7[5616:6696]: 1 items in the session cache 2010.03.24 11:54:54 LOG7[5616:6696]: 1 client connects (SSL_connect()) 2010.03.24 11:54:54 LOG7[5616:6696]: 1 client connects that finished 2010.03.24 11:54:54 LOG7[5616:6696]: 0 client renegotiations requested 2010.03.24 11:54:54 LOG7[5616:6696]: 0 server connects (SSL_accept()) 2010.03.24 11:54:54 LOG7[5616:6696]: 0 server connects that finished 2010.03.24 11:54:54 LOG7[5616:6696]: 0 server renegotiations requested 2010.03.24 11:54:54 LOG7[5616:6696]: 0 session cache hits 2010.03.24 11:54:54 LOG7[5616:6696]: 0 external session cache hits 2010.03.24 11:54:54 LOG7[5616:6696]: 0 session cache misses 2010.03.24 11:54:54 LOG7[5616:6696]: 0 session cache timeouts 2010.03.24 11:54:54 LOG6[5616:6696]: SSL connected: new session negotiated 2010.03.24 11:54:54 LOG6[5616:6696]: Negotiated ciphers: RC4-SHA SSLv3 Kx=RSA Au=RSA Enc=RC4(128) Mac=SHA1

This is where things time out; nothing happens beyond this point.