Is OpenSSH known to be less stable on Windows?

Yuri yuri at rawbw.com
Sat Oct 21 09:23:51 AEDT 2023


I run ssh-based reverse tunnels on Windows that allow external machines 
to connect to Windows.


When ssh was running as a native Windows process - there were problems.

Tunnels worked, but they randomly disconnected many times a day.

Additionally, sometimes it wasn't possible to connect to the existing 
tunnel from outside for unknown reasons.

The ssh server in the outside machine had to be restarted to allow for 
the next ssh connection.

Connections just stalled.


Then I moved the ssh process into the VirtualBox FreeBSD VM, so that the 
same tunnels now run through the FreeBSD-native ssh binary and into the 
same Windows machine.

Now all instability is gone. The tunnels run for many days in a row 
uninterrupted in the same Windows machine.


I am wondering: is ssh known to be less stable when it is built as a 
Windows executable?

Or, perhaps, Windows is more buggy?


Anybody has relevant experience or opinions?



Thanks,

Yuri




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