Windows 10 update cannot connect (behind a firewall)

pfsensewindows 10windows update

Why Windows 10 Update cannot connect to its update servers even though there is a working internet connection?

Screenshot of Windows 10 Update unable to connect

About my setup

  • Running Windows 10 on a PC behind a dedicated firewall (pfsense 2.2.5)
  • There is internet connectivity, port 80 / 443 works fine for anything else
  • Connecting the Windows 10 PC directly to my ISP's modem allows to update Windows 10 => suggests that the firewall is causing the problem

Already checked

Still, Windows 10 (version 1511) cannot update itself when I run it behind my firewall.

Any other suggestions/ideas?

Best Answer

Answering my own question.

I found the Windows Update Troubleshooter for Win10 from MS.

While running it, it in fact found and fixed a problem. After that, my Windows 10 can update itself now (great).

So, even though everything suggested a problem with my pfSense firewall it was some problem with the Windows Update itself.

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