I am using a Eudora client configured to use STARTLS to send mail through stunnel to a sendmail server. The stunnel config is as follows:

cert = /usr/local/etc/stunnel/stunnel.pem key = /usr/local/etc/stunnel/stunnel.pem socket = l:TCP_NODELAY=1 socket = r:TCP_NODELAY=1 options = DONT_INSERT_EMPTY_FRAGMENTS delay = yes TIMEOUTconnect = 300 TIMEOUTbusy = 300 setuid = smtpauth setgid = smtpauth debug = 7 client = no foreground = yes pid =

[smtps] accept = 465 connect = localhost:25 protocol=smtp

When I send mail the connection is established with port 465 on stunnel but it fails to negotiate the ssl session. THis is the log:

2007.03.06 15:45:08 LOG7[17753:1024]: Snagged 64 random bytes from /root/.rnd 2007.03.06 15:45:08 LOG7[17753:1024]: Wrote 1024 new random bytes to /root/.rnd 2007.03.06 15:45:08 LOG7[17753:1024]: RAND_status claims sufficient entropy for the PRNG 2007.03.06 15:45:08 LOG7[17753:1024]: PRNG seeded successfully 2007.03.06 15:45:08 LOG7[17753:1024]: Configuration SSL options: 0x00000800 2007.03.06 15:45:08 LOG7[17753:1024]: SSL options set: 0x00000800 2007.03.06 15:45:08 LOG7[17753:1024]: Certificate: /usr/local/etc/stunnel/stunnel.pem 2007.03.06 15:45:08 LOG7[17753:1024]: Certificate loaded 2007.03.06 15:45:08 LOG7[17753:1024]: Key file: /usr/local/etc/stunnel/stunnel.pem 2007.03.06 15:45:08 LOG7[17753:1024]: Private key loaded 2007.03.06 15:45:08 LOG7[17753:1024]: SSL context initialized for service smtps 2007.03.06 15:45:08 LOG5[17753:1024]: stunnel 4.20 on i686-pc-linux-gnu with OpenSSL 0.9.7l 28 Sep 2006 2007.03.06 15:45:08 LOG5[17753:1024]: Threading:PTHREAD SSL:ENGINE Sockets:POLL,IPv4 2007.03.06 15:45:08 LOG6[17753:1024]: file ulimit = 1024 (can be changed with 'ulimit -n') 2007.03.06 15:45:08 LOG6[17753:1024]: poll() used - no FD_SETSIZE limit for file descriptors 2007.03.06 15:45:08 LOG5[17753:1024]: 500 clients allowed 2007.03.06 15:45:08 LOG7[17753:1024]: FD 3 in non-blocking mode 2007.03.06 15:45:08 LOG7[17753:1024]: FD 4 in non-blocking mode 2007.03.06 15:45:08 LOG7[17753:1024]: FD 5 in non-blocking mode 2007.03.06 15:45:08 LOG7[17753:1024]: SO_REUSEADDR option set on accept socket 2007.03.06 15:45:08 LOG7[17753:1024]: smtps bound to 0.0.0.0:465 2007.03.06 15:45:08 LOG7[17753:1024]: No pid file being created 2007.03.06 15:45:18 LOG7[17753:1024]: smtps accepted FD=6 from 208.41.111.165:2542 2007.03.06 15:45:18 LOG7[17755:1026]: smtps started 2007.03.06 15:45:18 LOG7[17755:1026]: FD 6 in non-blocking mode 2007.03.06 15:45:18 LOG7[17755:1026]: TCP_NODELAY option set on local socket 2007.03.06 15:45:18 LOG5[17755:1026]: smtps accepted connection from 208.41.111.165:2542 2007.03.06 15:45:18 LOG7[17755:1026]: SSL state (accept): before/accept initialization 2007.03.06 15:45:20 LOG6[17755:1026]: init_ssl: s_poll_wait timeout 2007.03.06 15:45:20 LOG5[17755:1026]: Connection reset: 0 bytes sent to SSL, 0 bytes sent to socket 2007.03.06 15:45:20 LOG7[17755:1026]: smtps finished (0 left) 2007.03.06 15:47:00 LOG3[17753:1024]: Received signal 2; terminating

Can anyone tell me what I am doing wrong?

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