What's the most challenging bug you've ever encountered, and how did you resolve it?

Maybe you can go through: 30 Days of API Testing - Day 24: Share the best API bug you’ve found

There are several ‘best bug’ topics, I think someone started one a while ago but I think it’s already archived.

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Attack of the Codosaurus!: x == x = WTF?! got resolved mainly by talking to the original author to find out what he actually meant, and recoding it. It wasn’t that hard as it was a single line, but it was challenging (and I gladly did so) to actually understand what was going on under the hood to make the bug work the way it did.