I've done a couple coons this season where the tails really fought me. Had a hard time getting them started, then about half way down I could not get the hide to cut free of the tails. In both cases the tails broke when I pulled with my stripper, then the bottom couple inches of tail tore off when I tried to work out the piece of bone.

If this because I waited too long to skin them and they were stiff, or because they were both exceptionally fat coons? What are some tricks to deal with a tail that doesn't want to skin?

With the raccoon hanging from both hind legs I'll split the tail with my skinning knife to the tip if they are a problem but then I rarely ever used a tail stripper but relied on hand and arm strength and was skinning my own and for quite fur buyer .

With your sharp skinning knife cut down toward the tail bone to get through the tough grisly fat sometimes helps too then carefully pull the tail skin away from the back bone and tail bone even if you remove the hide from the carcass down further this can also help remove the tail from the tailbone .

For me it would be easier for me to show you than to explain by typing it ha ha
I hope this helps .
Allan

I always start from the small end of the tail and go towards the vent. You will find It a lot easier making the opening cut on the tail doing It this way. And that goes for every other critter where you have to remove the tail bone.

This is what I do...start a few inches down, then split to the vent. Then make sure you got plenty of loose skin down the back. Pull tail skin down to split, then you can ring it, to get through the fat. Now you should be able to use your strippers.

Interesting about working toward the vent. I’ll give that a try. My challenge with these last two wasn’t getting it started, it was getting the hide to pull away from the tail after a few inches.

Once you get it skinned down to the end of the split, take your knife and cut through the fat (very light cut) all the way around the tail bone.

Maybe your tail was frozen
I've never had a problem with them: split the tail from the vent down about 2 to 3 inches, put your tail stripper on pull tail stripper with one hand while holding the base of the tail with the other. Should pull off clean and easy. Don't use too big of a hole on the tail stripper

I can see the problem the OP had if the coons had been frozen whole and the tail freezer burned. The tip would be the first place the tail would dry out. But I do not see any reference to frozen but I also do not see a timeframe from dispatch to skinning either. It does seem unlikely that the tail would dry out enough to cause what he described but it sounds like it has happened more than once. I would be playing it back in my mind to try to determine what, if anything, was different on the ones I did not have a problem with versus the ones I did have problems with.

I do coon tails like trout, hold the tail in my left hand and run the knife tip to bung, just like gutting a trout. then peel and cut as need be.

It could have been frozen. The coons were outside in the cold all day until I could skin them that night. By that time they were stiff and not frozen solid, but the tails could have been.