I have been using stunnel previous versions just fine. It didn't apparently have the feature of a certificate in SSL server mode. That's alright but not necessary for us as we're simply running a localhost server to tunnel to the remote server. Anyway, I have read the FAQ tutorial and such related to this and tried everything. No mater what I do with the cert or key settings it still gives this same error here's the complete output.... No limit detected for the number of clients stunnel 4.53 on x86-pc-mingw32-gnu platform Compiled/running with OpenSSL 0.9.8s-fips 4 Jan 2012 Threading:WIN32 SSL:+ENGINE+OCSP+FIPS Auth:none Sockets:SELECT+IPv6 Reading configuration from file stunnel.conf FIPS mode is enabled Compression not enabled Snagged 64 random bytes from C:/.rnd Wrote 0 new random bytes to C:/.rnd PRNG seeded successfully Initializing service section [FIX] Section FIX: SSL server needs a certificate Server is down And here is the stunnel.conf file contents: ; Certificate/key is needed in server mode and optional in client mode cert = stunnel.pem ;key = stunnel.pem ; Disable support for insecure SSLv2 protocol options = NO_SSLv2 [FIX] accept = 127.0.0.1:5679 connect = 216.52.236.112:5680 TIMEOUTconnect = 5 [FIXLIVE] accept = 127.0.0.1:5680 connect = 216.52.236.185:51581 TIMEOUTconnect = 5 Please not that stunnel came installed with an stunnel.pem file. I tried uncommenting the config line for the key. Also regenerated the key using openssh per instructions. I tried using absolute path to the cert file. Nothing makes any difference. Is this a defect in stunnel? Or am I doing something wrong?