After updating stunnel to version 4.53 stunnel automatically starts after a reboot. Maybe something in the changelog helped? See: http://www.stunnel.org/?page=sdf_ChangeLog

More Info:

To update on FreeBSD 9.0 run the default supfile and update ALL ports (took me like 30 min): csup -g -L 2 -h cvsup5.us.FreeBSD.org /usr/share/examples/cvsup/ports-supfile

pkgtools was used for upgrading: portsdb -Fu portupgrade stunnel

After a reboot everything works.

/var/run/stunnel/stunnel.log

2012.07.21 15:04:06 LOG7[1376:675300096]: Clients allowed=5417 2012.07.21 15:04:06 LOG5[1376:675300096]: stunnel 4.53 on i386-portbld-freebsd9.0 platform 2012.07.21 15:04:06 LOG5[1376:675300096]: Compiled/running with OpenSSL 1.0.0e 6 Sep 2011 2012.07.21 15:04:06 LOG5[1376:675300096]: Threading:PTHREAD SSL:+ENGINE+OCSP Auth:LIBWRAP Sockets:POLL+IPv6 2012.07.21 15:04:06 LOG5[1376:675300096]: Reading configuration from file /usr/local/etc/stunnel/stunnel.conf 2012.07.21 15:04:06 LOG7[1376:675300096]: Compression not enabled 2012.07.21 15:04:06 LOG7[1376:675300096]: Snagged 64 random bytes from //.rnd 2012.07.21 15:04:06 LOG7[1376:675300096]: Wrote 1024 new random bytes to //.rnd 2012.07.21 15:04:06 LOG7[1376:675300096]: PRNG seeded successfully 2012.07.21 15:04:10 LOG6[1376:675300096]: Initializing service section [attsmtp] 2012.07.21 15:04:10 LOG7[1376:675300096]: SSL options set: 0x01000004 2012.07.21 15:04:10 LOG5[1376:675300096]: Configuration successful 2012.07.21 15:04:10 LOG7[1376:675300096]: Service [attsmtp] (FD=12) bound to 0.0.0.0:2525 2012.07.21 15:04:10 LOG7[1382:675300096]: Created pid file /stunnel.pid

On 07/21/2012 03:29 AM, John Vasko wrote:

On FreeBSD 9.0 stunnel 4.43 works fine after running "service stunnel restart", but stunnel fails loading on boot.

My desired config includes:

/usr/local/etc/stunnel/stunnel.conf

[attsmtp] client = yes verify = 0 accept = 2525 connect = smtp.att.yahoo.com:465 delay = yes

Please advise.

See below for messages after bootup:

/var/run/stunnel/stunnel.log

2012.07.21 02:52:06 LOG7[1378:675300096]: No limit detected for the number of clients 2012.07.21 02:52:06 LOG7[1378:675300096]: signal_pipe: FD=3 allocated (non-blocking mode) 2012.07.21 02:52:06 LOG7[1378:675300096]: signal_pipe: FD=4 allocated (non-blocking mode) 2012.07.21 02:52:06 LOG5[1378:675300096]: stunnel 4.43 on i386-portbld-freebsd9.0 platform 2012.07.21 02:52:06 LOG5[1378:675300096]: Compiled/running with OpenSSL 1.0.0e 6 Sep 2011 2012.07.21 02:52:06 LOG5[1378:675300096]: Threading:PTHREAD SSL:ENGINE Auth:LIBWRAP Sockets:POLL,IPv6 2012.07.21 02:52:06 LOG5[1378:675300096]: Reading configuration from file /usr/local/etc/stunnel/stunnel.conf 2012.07.21 02:52:06 LOG7[1378:675300096]: Snagged 64 random bytes from //.rnd 2012.07.21 02:52:06 LOG7[1378:675300096]: Wrote 1024 new random bytes to //.rnd 2012.07.21 02:52:06 LOG7[1378:675300096]: PRNG seeded successfully 2012.07.21 02:52:08 LOG6[1378:675300096]: Initializing SSL context for service attsmtp 2012.07.21 02:52:08 LOG7[1378:675300096]: SSL options set: 0x00000004 2012.07.21 02:52:08 LOG6[1378:675300096]: SSL context initialized 2012.07.21 02:52:08 LOG5[1378:675300096]: Configuration successful 2012.07.21 02:52:08 LOG7[1378:675300096]: libwrap_init: FD=5 allocated (blocking mode) 2012.07.21 02:52:08 LOG7[1378:675300096]: libwrap_init: FD=6 allocated (blocking mode) 2012.07.21 02:52:08 LOG7[1378:675300096]: libwrap_init: FD=6 allocated (blocking mode) 2012.07.21 02:52:08 LOG7[1378:675300096]: libwrap_init: FD=7 allocated (blocking mode) 2012.07.21 02:52:08 LOG7[1378:675300096]: libwrap_init: FD=7 allocated (blocking mode) 2012.07.21 02:52:08 LOG7[1378:675300096]: libwrap_init: FD=8 allocated (blocking mode) 2012.07.21 02:52:08 LOG7[1378:675300096]: libwrap_init: FD=8 allocated (blocking mode) 2012.07.21 02:52:08 LOG7[1378:675300096]: libwrap_init: FD=9 allocated (blocking mode) 2012.07.21 02:52:08 LOG7[1378:675300096]: libwrap_init: FD=9 allocated (blocking mode) 2012.07.21 02:52:08 LOG7[1378:675300096]: libwrap_init: FD=10 allocated (blocking mode) 2012.07.21 02:52:08 LOG7[1378:675300096]: accept socket: FD=11 allocated (non-blocking mode) 2012.07.21 02:52:08 LOG7[1378:675300096]: Option SO_REUSEADDR set on accept socket 2012.07.21 02:52:08 LOG7[1378:675300096]: Service attsmtp bound to 0.0.0.0:2525 2012.07.21 02:52:08 LOG7[1378:675300096]: Service attsmtp opened FD=11 2012.07.21 02:52:08 LOG7[1378:675300096]: Created pid file /stunnel.pid

2012.07.21 02:52:15 LOG7[1378:675300096]: Dispatching signals from the signal pipe 2012.07.21 02:52:15 LOG3[1378:675300096]: Received signal 2; terminating 2012.07.21 02:52:15 LOG7[1378:675300096]: str_stats: 43 block(s), 3554 byte(s) 2012.07.21 02:52:15 LOG7[1378:675300096]: removing pid file /stunnel.pid