Why is my leather holster doing this?

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Wow! Lots of bad advice here on the care and feeding of leather holsters. You do not want to soften the leather with conditioners, oils, Vaseline,etc.
As someone else mentioned... that is for boots and belts.

You want to stiffen the leather and lock down the nap. I use Gum Tragacanth, a specialty product, but you can use a 50/50 mix of Mop & Glo (or similar product) with water. It will not take much.
Coat the surface. Do not use a ton of this stuff. It should be absorbed by the leather, not standing on the surface. Then burnish (smooth) the nap down with something like the handle of a butter knife and let it dry at room temperature. That's it. Do not put it in the oven.

When wet molding holsters, they are often force dried in an oven at 120° or LESS, but this is before dying and finishing, etc.
Never expose your holster to temps that would burn your hand. High heat can burn or char the leather, dry it out and it will get brittle and crack.
 
Addendum, in acknowledgement of some comments that were on point...

Yes, if you burnish down the nap, it can eventually loosen up again later, if you frequently draw and holster.

Yes, a lined holster is the absolute answer to this type of problem.
 
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