Beware of the proxy!

Had a (somewhat) interesting case the other day – after (finally) upgrading my Windows Admin Center (WAC) gateway machine to the new Windows Server 2022, my WAC suddenly stopped working. I couldn’t connect to any of the servers from within the console, couldn’t add new ones, … nothing.

When tried adding new servers, nothing happened – wizard stays at “Searching for…“:

Even PowerShell couldn’t connect anymore (which is actually the root cause of the above).

So, what happened?

Everything worked before and I wasn’t aware of other changes… other than upgrading my OS (in-place upgrade, Windows Server 2019 to Windows Server 2022), that is.

Let’s try and make sense of all this.

Test-NetConnection says everything is fine, Test-WSMan from another machine works:

However, Test-WSMan from this (WAC) machine simply doesn’t work:

Tried checking the logs next – two errors inside Applications and Services Logs -> Microsoft -> Windows Remote Management -> Operational log caught my eye:

  • Error 138: The client got a timeout from the network layer (ERROR_WINHTTP_TIMEOUT)
  • Error 142: WSMan operation Identify failed, error code 2150859046

So, it’s something with the network after all – more specifically, seems like there is some issue on the HTTP/S part!

After some thinking, I remembered that we have a HTTP/S proxy in our network – maybe my PowerShell session actually tries to go through it?! 😀

Checking if proxy is set (with netsh winhttp show proxy) – it is! This could be the issue.

Now I’m resetting the proxy settings (with netsh winhttp reset proxy, of course):

And then trying Test-WSMan again:

It finally works! And WAC works as well! 😀

Hope this helps!


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