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My Windows 10 client wouldn’t connect to our Direct Access severs today, kept just getting Connecting

So to troubleshoot I’d recommend:

Checking your internet connection:

Now its worth running some PowerShell commands to get the actual error:

Get-NetIpHttpsState

This likeley means your proxy is in the way of your connection.

Check the settings:

Get-NetIPHttpsConfiguration

Double check your internet connection

Test-NetConnection

I think its time to check the proxy settings:

Check if you can get to a website via IE and try via another browser such as Firefox.

If you cant then check if your proxy is off:

Now check the windows 10 proxy and the Netsh proxy:

Windows 10, turn it off:

Check the netsh and then turn it off or reset it to IE:

#Show the proxy settings:
netsh winhttp show proxy
#Reset it to default
netsh winhttp reset proxy
#Set to IE
netsh winhttp import proxy source=ie

When reset should look like this:

Failing that reset the IP Helper in services.msc or reboot:

The netsh settings fixed it for me, the reason I’d set it was to allow PowerShell out to the internet for Exchange 365 work.