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How can I use Windows AutoPilot with a Proxy ?

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my experience was back when I wrote the script used in this blogpost, and at that time, it was the only way I could get Windows Autopilot to work in our environment. Our environment has changed since then and no longer uses the same type of proxy, you could say now that it now resembles a transparent proxy and therefore there's no longer any need to use the script.

if you can, avoid using Hybrid azure ad join, it's more trouble than it's worth.

When I initially wrote the script it was so that we could test Windows Autopilot on the internal LAN, a lot has changed since then and we've learned a lot too. The best advice I can give you is to try modifying this script to work with your environment, or determine if you need it at all based on what happens in Windows Autopilot, maybe you can add exclusions for the urls used during Windows Autopilot, there are lots of options.

as regards point 3, you could always use a different network (think of it as an enrollment network) to get your devices through Windows Autopilot OOBE and complete enrollment, you could then apply whatever network/proxy settings you want AFTER windows autopilot is complete using some of the methods I describe here

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To use Windows AutoPilot with a proxy, you need to ensure that your device can communicate with the required endpoints over the network. Here are the steps to follow:

  1. Determine the URLs or IP addresses that your device needs to communicate with to use Windows AutoPilot. These include the Microsoft Endpoint Configuration Manager service, the Microsoft Store for Business and Education, and the Microsoft Intune service.
  2. Configure your proxy server to allow traffic to these URLs or IP addresses.
  3. Configure your device to use the proxy server. You can do this either during device setup or by modifying the device's network settings later on.
  4. If you're using a web proxy, ensure that it supports SSL interception and decryption, as Windows AutoPilot requires SSL inspection.
  5. Verify that your device can communicate with the required endpoints over the network. You can use tools like telnet, ping, or nslookup to test connectivity.

Once you've completed these steps, you should be able to use Windows AutoPilot with a proxy. Note that some proxy servers may require additional configuration, such as authentication or SSL certificate installation. Consult your proxy server documentation for more information.


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