WinHTTP settings must be configured in UI under certain conditions/platforms
I came across an interesting issue the other day and thought I'd share in case I'm not the last person to find out about quirky Microsoft behavior.
Short "TLDR" Version: IF you’re using Windows Server 2016 (or Windows 10) and IF you’re using applications running with dedicated service accounts, and IF you need WinHTTP to use a proxy for those apps, you MUST configure proxy settings under the UI. Configuring proxy settings using netsh is not sufficient under these platforms/conditions.
Longer Version: In Windows 10/2016, command-line use of netsh winhttp proxy will apply to System Accounts and Services but not dedicated Service Accounts. Instead, to get this working for Windows 10/2016 with Service Accounts, you must configure proxy details via the "modern apps UI".
Specifically, this means:
1) Authenticating to Windows as the service account itself (you may need to elevate permissions on the service account).
2) Navigate to the Network and Internet UI (via the command start ms-settings: from command-prompt or PowerShell
3) Select Proxy from the UI sidebar.
4) Update the Manual proxy setup section with the relevant details.
Microsoft has some limited information here.
Anyway, just wanted to pass this along as it doesn't seem to be broadly known and this could definitely confuse folks (like myself!) who are accustomed to using netsh for everything.
