I've made a WPAD server Fiddler extension and in a fit of creativity I've named it: WPAD Server Fiddler Extension.
Of course you know about Fiddler, Eric's awesome HTTP debugger tool, the HTTP proxy that lets you inspect, visualize and modify the HTTP traffic that flows through it. And on the subject you've probably definitely heard of WPAD, the Web Proxy Auto Discovery protocol that allows web browsers like IE to use DHCP or DNS to automatically discover HTTP proxies on their network. While working on a particularly nasty WPAD bug towards the end of IE8 I really wished I had a way to see the WPAD requests and responses and modify PAC responses in Fiddler. Well the wishes of me of the past are now fulfilled by present day me as this Fiddler extension will respond to WPAD DHCP requests telling those clients (by default) that Fiddler is their proxy.
When I started working on this project I didn't really understand how DHCP worked especially with respect to WPAD. I won't bore you with my misconceptions: it works by having your one DHCP server on your network respond to regular DHCP requests as well as WPAD DHCP requests. And Windows I've found runs a DHCP client service (you can start/stop it via Start|Run|'services.msc', scroll to DHCP Client or via the command line with "net start/stop 'DHCP Client'") that caches DHCP server responses making it just slightly more difficult to test and debug my extension. If a Windows app uses the DHCP client APIs to ask for the WPAD option, this service will send out a DHCP request and take the first DHCP server response it gets. That means that if you're on a network with a DHCP server, my extension will be racing to respond to the client. If the DHCP server wins then the client ignores the WPAD response from my extension.
Various documents and tools I found useful while working on this: