Great thread! I have to admit I have run afoul of airport security twice, both times pre-TSA as I recall. The first time my wife was a flight attendant in Chicago and was issued a sticker to put on our car windshields that allowed access to O'Hare on field parking, was always fun yielding right of way to a 747 before crossing the taxiway! I parked in the employee lot on the field and took the employee bus to the terminal which dropped me off at the gates past security. We were going to Mexico and I was going to go SCUBA dive and had a quite large dive knife in my bag, no problem as I went through no screening. Upon our return we flew through Mexico City, had to go through their screening and the knife was detected and it was confiscated, hope someone got a nice knife.
The second time was entirely my fault. I was going down to Memphis to visit my daughter attending college there. Before going to the airport I was on my computer renting a car and they required my Driver License info and I inadvertently left it at home after entering the required info. I got to security and they asked for a photo ID, it was back at home! They said if it I had two major credit cards they could allow me to board with some type of credit check. I asked if there would be an issue returning from Memphis and they assured me no. Excellent, I had to go through a special screening and low and behold I had a Swiss Army knife in my pocket I had carried for 30 years. I was sure it was arrest time but they allowed me to put it in my bag and check it and problem averted. When I went to return from Memphis, boarding denied! I asked for the supervisor and calmly resolved the issue so am not still in Memphis.
Not so much of a security issue but a bit of a funny story. I went to New Zealand fishing in February and having been there several times before I always had to go through biosecurity to have my waders, boots, and all gear checked, no problem. I was so busy fishing I never checked the news until the day before my return in March, virus was crazy! I could not a flight out of Auckland to USA so flew up to Sydney Australia to catch a flight home. I declared all my fishing gear and of course was diverted to Aussie biosecurity as expected. The officer asked how long I was going to be in OZ and I showed him my return ticket for the next day. He responded, " you are not going fishing obviously" , closed my bags and said get going mate.