WPAD and Proxy Auth Cause Exchange HCW to Fail

A recent conversation with a colleague reminded me of an issue I’ve faced a number of times (and forgotten to blog about) when running the Exchange Hybrid Configuration Wizard (HCW) on Exchange 2010 or 2013 in an environment where Web Proxy Autodiscovery Protocol (WPAD) is used.

The Problem

The most common scenario where I’ve seen this come into play is along the lines of this:

  1. WPAD is used to distribute Proxy.PAC to client machines
  2. Customer permits direct connection from Exchange servers to Internet
  3. From an elevated command prompt, run “netsh winhttp reset proxy” to ensure a direct connection
  4. Change Internet Options settings from “Automatically detect settings” to “Disabled”
  5. Browse to a site restricted by the proxy to confirm proxy bypass is working
  6. Can connect to Exchange Online using Remote PowerShell
  7. Run the HCW but it fails with the following error in the logs:
    ERROR : System.Management.Automation.RemoteException:
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Do It Yourself Fiddler Service

I recently upgraded to Windows 8.1 which required a full install (upgraded from the 8.1 Preview which annoyingly didn’t support upgrades). A full install of my laptop is getting easier and easier as more of the things I use are delivered as services. The install list is getting smaller due to the combined effect of software as a service and a simpler working life.

I still had to install these:

  • Microsoft Office 2013
  • Microsoft Visio 2013
  • Microsoft Project (yes yes I know but there really is no good alternative yet)
  • LastPass
  • Visual Studio 2013
  • And…Fiddler!
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