Here's what worked for me:
I used a ceramic tile on my table. I also used a screwdriver with a plastic handle that pretty much fit inside the insert with a little room to move around. Didn’t use a socket because I didn’t want cold metal that would cool down the plastic insert immediately.
With the insert face up on the tile, heat with heat gun on low about 4" - 8” away , moving the heat around. I did it face up so the surface would soften but not so much the sides. After about 10-15 seconds, flip it over and press down with the screwdriver handle. Keep pressing until you think the plastic has cooled. Flip it right side up and place a pinball on it. That shows you if you are good or need to keep working on it. You might have to repeat & press flat with the screwdriver in another place.
If the sides of the insert are warped, you can use the heat and something round like a wooden dowel to work it back into shape.
I was working on inserts from a 1961 Gottlieb. Your mileage may vary.