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I have a Mac OSX host and I'm running Parallels (but the same problem exists in VirtualBox). The scenario is that the Mac is wired into a corporate network with an explicit proxy set. The VM running Windows Server 2012 is using a bridged adapter and also connecting to the same explicit proxy in LAN Settings.

When I start fiddler, no traffic is going through the VM. If I change the Mac's proxy settings to point to the VM-IP:8888 then fiddler traffic shows up from the Mac.

How can I get Windows traffic to go through Fiddler?

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