Mailing List Archive: Is OpenSSH known to be less stable on Windows?

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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If this is the native version of openssh
(github.com/PowerShell/open-ssh-portable) then it includes a pretty
extensive win32 compatibility layer. That may be the source of the
problem. You may want to post an issue request there as they'll be in a
place to do something about it. If you can build off of the git, using
VS, the version at the head of the git repo is based on 9.4p1 rather
than, I think 8.7p1 so there might be some fixes in it.

The person maintaining that repo seems to be relatively responsive.

Chris

On 10/20/23 6:23 PM, Yuri wrote:
> 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
>
>
> _______________________________________________
> openssh-unix-dev mailing list
> openssh-unix-dev@mindrot.org
> https://lists.mindrot.org/mailman/listinfo/openssh-unix-dev
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