I am having problems connecting to stunnel and was hoping someone could help me.

When starting stunnel and then trying to send an SSL-encrypted email through it I get:

$ sudo /usr/local/sbin/stunnel /sw/etc/stunnel/stunnel.conf -D 465 -r 25 2006.10.04 11:03:28 LOG7[29230:2684415368]: Snagged 64 random bytes from /Users/jlbrown/.rnd 2006.10.04 11:03:28 LOG7[29230:2684415368]: Wrote 1024 new random bytes to /Users/jlbrown/.rnd 2006.10.04 11:03:28 LOG7[29230:2684415368]: RAND_status claims sufficient entropy for the PRNG 2006.10.04 11:03:28 LOG7[29230:2684415368]: PRNG seeded successfully 2006.10.04 11:03:28 LOG7[29230:2684415368]: Certificate: /Users/ jlbrown/%1.pem 2006.10.04 11:03:28 LOG7[29230:2684415368]: Certificate loaded 2006.10.04 11:03:28 LOG7[29230:2684415368]: Key file: /Users/jlbrown/% 1.pem 2006.10.04 11:03:28 LOG7[29230:2684415368]: Private key loaded 2006.10.04 11:03:28 LOG7[29230:2684415368]: SSL context initialized for service ssmtp 2006.10.04 11:03:28 LOG5[29230:2684415368]: stunnel 4.18 on powerpc- apple-darwin8.8.0 with OpenSSL 0.9.7i 14 Oct 2005 2006.10.04 11:03:28 LOG5[29230:2684415368]: Threading:PTHREAD SSL:ENGINE Sockets:SELECT,IPv4 Auth:LIBWRAP 2006.10.04 11:03:28 LOG6[29230:2684415368]: file ulimit = 256 (can be changed with 'ulimit -n') 2006.10.04 11:03:28 LOG6[29230:2684415368]: FD_SETSIZE = 1024 (some systems allow to increase this value) 2006.10.04 11:03:28 LOG5[29230:2684415368]: 125 clients allowed 2006.10.04 11:03:28 LOG7[29230:2684415368]: FD 6 in non-blocking mode 2006.10.04 11:03:28 LOG7[29230:2684415368]: FD 7 in non-blocking mode 2006.10.04 11:03:28 LOG7[29230:2684415368]: FD 8 in non-blocking mode 2006.10.04 11:03:28 LOG7[29230:2684415368]: SO_REUSEADDR option set on accept socket 2006.10.04 11:03:28 LOG7[29230:2684415368]: ssmtp bound to 0.0.0.0:465 James-Browns-Computer-2:~/stunnel-4.18 jlbrown$ 2006.10.04 11:03:28 LOG7[29231:2684415368]: Created pid file /usr/local/var/run/stunnel/ stunnel.pid 2006.10.04 11:08:08 LOG7[29231:2684415368]: ssmtp accepted FD=9 from 127.0.0.1:64235 2006.10.04 11:08:08 LOG7[29231:25188864]: ssmtp started 2006.10.04 11:08:08 LOG7[29231:25188864]: FD 9 in non-blocking mode 2006.10.04 11:08:08 LOG7[29231:25188864]: TCP_NODELAY option set on local socket 2006.10.04 11:08:08 LOG7[29231:25188864]: FD 10 in non-blocking mode 2006.10.04 11:08:08 LOG7[29231:25188864]: FD 11 in non-blocking mode 2006.10.04 11:08:08 LOG7[29231:25188864]: Connection from 127.0.0.1:64235 permitted by libwrap 2006.10.04 11:08:08 LOG5[29231:25188864]: ssmtp connected from 127.0.0.1:64235 2006.10.04 11:08:08 LOG7[29231:2684415368]: Cleaning up the signal pipe 2006.10.04 11:08:08 LOG7[29231:25188864]: FD 10 in non-blocking mode 2006.10.04 11:08:08 LOG7[29231:25188864]: ssmtp connecting 127.0.0.1:25 2006.10.04 11:08:08 LOG7[29231:25188864]: connect_wait: waiting 10 seconds 2006.10.04 11:08:08 LOG6[29231:2684415368]: Child process 29421 finished with code 0 2006.10.04 11:08:08 LOG7[29231:25188864]: connect_wait: connected 2006.10.04 11:08:08 LOG7[29231:25188864]: Remote FD=10 initialized 2006.10.04 11:08:08 LOG7[29231:25188864]: TCP_NODELAY option set on remote socket 2006.10.04 11:08:08 LOG7[29231:25188864]: SSL state (connect): before/ connect initialization 2006.10.04 11:08:08 LOG7[29231:25188864]: SSL state (connect): SSLv3 write client hello A 2006.10.04 11:08:08 LOG7[29231:25188864]: SSL alert (write): fatal: handshake failure 2006.10.04 11:08:08 LOG3[29231:25188864]: SSL_connect: 1408F10B: error:1408F10B:SSL routines:SSL3_GET_RECORD:wrong version number 2006.10.04 11:08:08 LOG5[29231:25188864]: Connection reset: 0 bytes sent to SSL, 0 bytes sent to socket 2006.10.04 11:08:08 LOG7[29231:25188864]: ssmtp finished (0 left)

Any suggestions as to what is causing this and how I can fix it?

I got the same thing on another machine, with stunnel 4.04 and OpenSSL 0.9.7d.

My stunnel.conf file is:

cert = /Users/jlbrown/%1.pem key = /Users/jlbrown/%1.pem debug=7 output=/dev/stdout ; Some performance tunings socket = l:TCP_NODELAY=1 socket = r:TCP_NODELAY=1 ; Service-level configuration [ssmtp] client = yes accept = 465 connect = 192.168.1.31:25

Thanks,

James.