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Most of the forums I have seen are really lame pirate-oriented sites. I am interested in joining in a discussion with programmers about building iOS software that breaks the rules, but not illegal stuff.

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You could try Stack Overflow, a Q&A site like this one. There are occasionally jailbreak app questions on there, but most iOS questions are for the App Store, so you will need to explicitly say that jailbreak solutions are ok, and a dedicated site would probably give better results. –  ughoavgfhw Nov 19 '12 at 20:36

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A number of developers are on IRC on Saurik's IRC network: irc.saurik.com (port 6697 for SSL). Channels include #cycript, #cydia, #iPhone, #iphonedev, and #theos (for tweak development).

Also note you will probably get better answers to jailbreak questions at Jailbreak QA. No questionable questions are allowed there. And you will not get a good response if you have questionable repositories in your Cydia configuration. Just how things are.

Most forums I have found regarding iOS hacking usually involve piracy at some level (whether that be getting apps or in-app purchases for free).

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