Stunnel as Windows service doesn’t “start” on reboot

stunnelwindows-server-2008windows-service

Running stunnel 5.03 on Windows 2008 R2.

Everything is installed and working fine. I can even start/stop the service no problem…

When I reboot my server stunnel service shows as started but nothing gets logged and none of my connections work. Once i restart the service through service manager, everything works. So on startup it doesn't seem to run…

This only happens if i reboot the machine.

Output of my logs proving it works. 

2014.09.11 15:57:48 LOG5[1612]: stunnel 5.03 on x86-pc-msvc-1500 platform
2014.09.11 15:57:48 LOG5[1612]: Compiled/running with OpenSSL 1.0.1i-fips 6 Aug 2014
2014.09.11 15:57:48 LOG5[1612]: Threading:WIN32 Sockets:SELECT,IPv6 SSL:ENGINE,OCSP,FIPS
2014.09.11 15:57:48 LOG5[1612]: Reading configuration from file stunnel.conf
2014.09.11 15:57:48 LOG5[1612]: FIPS mode disabled
2014.09.11 15:57:49 LOG5[1612]: Configuration successful

Best Answer

The most obvious thing is to make sure that the service is set to 'Automatic.'

Are there any events in EventViewer relating to the startup of this service post-reboot?

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