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An old car I used to have had a worn down ignition key that would start the car and I could pull it out while it was running with that particular key. My other keys that were not worn down would not come out.So, is your key heavily worn down?
It sure sounds like an ignition switch and new key cylinder is in order.
Anecdotally, I learned about the GM passkey protections the hard way a few years back with a Cadillac Escalade. It didn't dawn on me that GM would still be THAT concerned about theft of a radio, but we discovered that cycling the key without the radio installed netted us a completely locked down Escalade. I had the car for a motion picture cannon gag, so we basically gutted the interior, installed a full roll cage, pyrotechnic cannon and fuel cell. I cannot say if it was only cycling the ignition one time, or a series of times, without the radio plugged in that caused the padlock to appear in the heads up and meant bringing in someone with the correct scan tool and software to rectify. We still wound up "sending" the truck with the aftermarket stereo covered in foam and gaffers-tape and zip-tied to one of the roll cage bars. The stuntie driving wasn't super excited to have the thing in his "office space", but it was the only way I could be certain the truck would start and run while when the expense of cameras running happened. I'm sure there are ways around it, and reading the thread it seems you have gotten past it all. Sorry for being late to the party with relevant information all the same. Be safe Jeremy