Monitor your Mac traffic through Fiddler on your Windows VM

I work on a Mac computer. I develop both on Mac and Windows.
A lot of times I find myself trying to intercept some traffic coming from my Mac on my Fiddler instance which lives on my Windows VM. The main reason for this is the fact that I haven’t been able to successfully use Fiddler on Mac in a native way.

Eric Lawrence, the creator of Fiddler has a pretty interesting article which helps a lot to achieve the above. The main points are the following:

  1. Install VirtualBox and create a Windows or Linux virtual machine.
  2. In VirtualBox Manager, select the VM and click the Settings icon at the top of the window.
  3. Click the Network icon at the top of the window and change Attached to: to Bridged Adapter. Click Ok.
  4. Start the Virtual Machine and install Fiddler.
  5. Start Fiddler and click Tools > Fiddler Options > Connections. Tick the “Allow remote computers to connect” box.
  6. Restart Fiddler.
  7. Note the IPv4 address of the Fiddler instance by hovering over the Online icon in Fiddler’s toolbar, or run ifconfig eth0 in the terminal (Linux) or ipconfig (Windows).
  8. On the Mac, click the Apple Menu > System Preferences > Network.
  9. Click the Advanced button.
  10. On the Proxies tab, Enable the Web Proxy (HTTP) and Secure Web Proxy (HTTPS) options to point to the IPv4 address of the virtual machine (found in Step #7) using port 8888.
  11. To decrypt HTTPS traffic, you’ll need to install the HTTPS certificate in the Mac’s keychain. You can download this certificate by visiting the http://IPAddress:8888.


Find the original article from Eric here.

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