Extraction Problem 99f in. 308

My new to me 99f is giving me issues with extraction. I have discovered the chamber is a bit rough but that doesn't fully explain why the extractor pops off the rim with even moderate effort. I have cleaned the cutout for the extractor on the edge of the chamber and the headspace seems okay but I will have it checked. The extractor doesn't look worn or damaged. I haven't disassembled as there is no stickiness of the extractor in the bolt. Has anyone experienced this and what was the solution?

Further examination revealed that the extractor has no tension on the rim. It pivots freely on the extractor pin. Is this normal? I would have thought it would have some spinginess in it so it would hold into the extraction groove better. I do not have access to another rifle for comparison.

Update. I disassembled and cleaned everything. I cleaned and polished the chamber and tapped the tip of the extractor inward a smidgeon with a plastic faced hammer while using a small camp to keep the extractor from bowing in the middle. This gave it more spring tension and it now grips the rim much better. I will be ordering a new extractor. Even with polishing the chamber is tight indicating it was probably cut with a worn reamer. I will have to FL size and maybe even invest in a small base die As an aside the trigger spring was helical not flat and obviously the trigger mechanism slightly different than my schematic showed. I also had to remove the lever bushing and screw and pull the lever away somewhat to get the bolt out. This is not what the disassembly instructions indicate but I couldn't get it out any other way.

For those who may want to disassemble a 99 watch that auto cutoff spring. After removing the bolt stop hold the rifle so the auto cutoff and spring fall out the port when you bring the bolt back to remove. I ddn't and the spring fell inside the rotary magazine. After hunting all over my bench and the floor I finally found, it using a bore light, in the mag and got it out with some long forceps.

It goes to the gunsmith Monday to have headspace checked.

Update. Headspace is okay but the gunsmith fired a factory round and it also stuck tight. He is further evaluating but perhaps a cylinder honing is needed.

Final post. Cylinder has been honed and now factory rounds cycle without sticking. Tightest chamber g'smith has seen outside of a custom barrel. Chamber was also rough with machining ridges very evident. My original thoughts about a worn reamer remain. The previous owner must have either been a reloader or very patient. Rifle was made in 1964!