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In the attached image I have established an SSH tunnel that should allow me to resolve network requests through the remote (in this case a virtual machine containing Ubuntu).

However I am unable to resolve URLs when connected to the proxy.

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The computer is connecting to an Ubuntu guest running on Hyper V. The guest has access to the outside world via an external virtual switch

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EDIT:

When attempting to connect to the VM guest on an external device (Macbook) everything works fine and I am able to resolve URLs through the VM's network. The MacBook is a physically separate device but connected to the same local network, with network access to the VM.

See working screenshot below

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EDIT:

I have attempted to connect to the VM from an external Windows laptop and had the same issue, leading me to believe it's the way I am setting up my Windows proxy.

EDIT:

Using proxifier works on Windows, but I am not really happy with that solution

EDIT:

Firefox's manual proxy settings works

EDIT:

It was a bug with the Windows metro UI

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So it turns out it's just a bug with Windows Metro GUI. To enable a SOCKS proxy you must use the old Control Panel and traverse your way through to set the proxy the old way.

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  • This worked when using Windows 11 built-in OpenSSH. Wow. Still doesn't work with WSL2 however.
    – naisanza
    Commented Jan 29, 2023 at 20:37

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