Activate Windows through a proxy

Being a system administrator for a company using more than 150 machines I can end up in the situation where I am setting up multiple new machines at once. For the initial roll-out of OS and accompanying software we use a FOG server, but we still need to login and activate Windows before giving the machine to a user.

When we originally tried to activate Windows through our proxy we came across this error: Windows activation fails and may generate error code 0x8004FE33 this was because the PC wasn’t able to communicate with the Windows Activation servers through our proxy server.

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To combat this we had to give the machine an IP that bypassed our proxy and used a Firewall policy that allowed unrestricted web access in order for the machine to connect to the Microsoft Windows Activation servers. This wasn’t ideal both from a security standpoint and it meant that setting up a machine for a user took longer than anticipated. Then I had the idea of adding the Microsoft Windows Activation servers to the proxy bypass list on the proxy itself. This meant that an unauthenticated user (e.g. an administrator account) was able to communicate through the proxy in order to activate Windows. This assumes that the proxy details are already applied to the machine, we get ours via Group Policy.

The the list of servers to bypass authentication for are here:

  • go.microsoft.com
  • sls.microsoft.com
  • crl.microsoft.com
  • www.microsoft.com
  • activation.sls.microsoft.com

I won’t detail how to add these to your proxy as the process is different for each proxy. Please refer to your proxy server documentation for the steps required to do this.

This was Activate Windows through a proxy.

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