[stunnel-users] Getting Stunnel to Work Under Windows 7 64-bit

Thomas Eifert kxkvi at wi.rr.com
Sat Apr 28 23:38:59 CEST 2012

For the benefit of the group, I thought I'd share some experiences I had 
when attempting to get
Stunnel to run under Windows 7 SP1 64-bit.

I initially installed Stunnel version 4.53 to the default location, 
which in Windows 7 64-bit is:

C:\Program Files (x86)\stunnel\

I installed the service from the start menu option, then rebooted my 

I have administrator rights, and User Account Control is disabled.  My 
included the following:

1.  The Stunnel status window displayed only configuration loads.  No 
output from any
       active connection was ever displayed, despite the fact that 
Stunnel was passing
       traffic to/from SSL-enabled servers.

2.  Stunnel would not write to the log file.  The error message 
indicated that Stunnel was
       unable to open stunnel.log.  Initially, I thought this might be a 
factor in the lack of
       status window connection output, so I commented the log statement 
out to eliminate it.
       I then reloaded the configuration.  The issue of not seeing any 
connection info
       was unaffected.

3.  The notification area icon would not appear on Stunnel service 
load.  It would mysteriously
       appear, then disappear, at seemingly random times.

4.  Once the service was installed, it was not possible to stop it or 
uninstall it from the
       provided start menu shortcuts.  Whenever I attempted to do so, 
the Stunnel status
       window would appear.  However, I was able to perform these 
actions successfully by
       opening a command prompt, then issuing the commands from there.

In an effort to unravel these issues, I tried the following workarounds:

1.  I re-installed stunnel to a non-system controlled directory.  In my 
case, it was C:\Apps\stunnel\.

  2. I attempted to run stunnel in compatibility mode, set for Windows 

  3. I tried installing 2 previous versions of Stunnel.

All combinations produced exactly the same undesired result.

Finally, I stopped and uninstalled the service.  Instead of using that 
method, I created a
shortcut to stunnel.exe, and placed it in the start menu's startup 
folder, then rebooted.

Stunnel started at boot time, and all of the above issues were resolved.

As such, it seems like Stunnel just doesn't like to be run as a service 
on a Windows 7 64-bit
machine; at least not on the one I own.

If you're encountering any stability issues with the Stunnel service in 
the Windows 7 64-bit
environment, try my method.  It works.

I'd like to extend a special thank you to Carter Browne, who provided 
valuable input throughout
the course of my testing.



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