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If you configure an HTTPS proxy, the client will use the proxy's name to verify the connection to the proxy and trust that the proxy will verify the remote connection.

If you're trying to configure transparent proxying where the network redirects traffic to a different device, you would need to have a local CA so you can forge certificates — that's not uncommon in enterprise IT but it's definitely a security risk associated to having something which can MITM anything on your network.

In either case, the real question is whether you control the endpoint. If it doesn't support configuring a proxy or installing a CA, all you have is the binary decision to decide whether or not to allow it on the network at all since whoever does control the client has so many options for smuggling traffic out.



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