What's the most challenging bug you've ever encountered in your programming career, and how did you eventually solve it?
I’ll start. The only one I can recall from the recent past is not realizing that you can’t use a MySQL transaction from within a persistent connection. Here’s when I learned that lesson.
As far as the single biggest threat to my career from a technical perspective, I would have to definitively say the miscommunication between myself and James that lead to our database being hacked in 2015. We are still experiencing the fallout from that today.
How about everyone else?