If changing ammo changes the symptom you're seeing, it might save you the trouble of trying to remove the extractor.
Armorers are told that the extractors should only be removed for repair use, implying they aren't something to be removed & reinstalled with any frequency.
The use of the starter punch to break the pin loose (from the top) requires a thick-tipped (tapered) punch, but it shouldn't be driven down into the hole (to avoid wallowing out the hole). That's why the 1/16" pin punch with a long & straight shank is used to do most of the moving once the pin is freed within the hole.
The pins are originally installed using a heavy press, and I've had it require significant whacking with a 4oz ball peen hammer in order to break a pin loose and start it moving.
It's often easiest to keep the orientation of the pin in mind (top/bottom) when reinstalling the pin, too, so it can be reinstalled in the same orientation.
I've seen a slide which had been ruined because someone had tried to hammer a pin out of the slide, bottom-to-top (wrong direction), apparently using the wrong tools in a ham-handed manner. The top half of the slide's pin hole (above the extractor) had been wallowed out so badly that it would no longer hold the pin stable, and the bottom was chewed up REALLY badly.
FWIW, armorers are reminded that ruining the pin hole ruins the slide. There are NOT any "over-size" extractor pins available for repair, nor are roll/coil pins used. The hole in the extractor is sized to work properly with the existing solid pins.
When an extractor is "sticky" toward the front (or has a too-heavy extractor spring) it usually results in feeding problems ... and when it's "sticky" toward the rear (or has a too-light spring tension) it usually results in failures-to-extract.
Here's a couple of 9mm ejectors. The bottom one is the original 3rd gen part, with a short tip and a sharp-cornered angle under the back of the tip where it blends with the body. The top ejector is a revision, with a longer tip for faster ejection (especially with more powerful loads) and a curved angle to reduce the potential for a stress riser at on the bottom of the tip toward the rear.