I am looking to get access to all HTTP traffic on my machine (my windows machine - not a server). From what I understand having a local proxy through which all traffic routes is the way to go. I have been Googling but failed to find any resources (in respect to Ruby) to help me out. Any tips or links are much appreciated.
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Is having a proxy built in Ruby the important point here? Or just to "get access to all HTTP traffic on your machine"? If the latter, there's a free program called HTTP Sniffer and Analyzer that can supposedly do this. I have not used it but I have seen it get some positive reviews. There are several other such programs, though most seem to be paid. On OS X, Linux, etc, you can use the in-built tcpdump in clever ways to get a similar effect.
There's an HTTP Proxy in WEBrick (part of Ruby stdlib) and here's an implementation example.
If you like living on the edge there's also em-proxy by Ilya Grigorik.
This post by Ilya implies that it does seem to need some tweaking to solve your problem.