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

[Thomas Eifert]

In my previous post, I neglected to include a relevant snippet from my 
stunnel.conf file.

Here it is:

debug = 6
fips = no
delay = yes
output = stunnel.log

[nntps.1]
client = yes
options = NO_SSLv2
sslVersion = TLSv1
ciphers = DHE-RSA-AES256-SHA:DHE-DSS-AES256-SHA:AES256-SHA
cafile = peer-nntps.1.pem
verify = 4
accept = 127.0.0.1:119
connect = xxx.xxx.xxx.xxx:563


On 4/28/2012 4:38 PM, Thomas Eifert wrote:
> 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 
> machine.
>
> I have administrator rights, and User Account Control is disabled.  My 
> observations
> 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 
> XP SP3.
>
>  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.
>
> Regards,
>
> Thomas
>

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