Ouch. Stripping a security torx screw is quite an achievement, honestly. The cam-out torque on these screws should be far higher than what you should be tightening them to on the Sentry. Maybe check the head of the screwdriver you are using, it could be chipped or broken in some way that's causing it to slip more easily than it should.
The best my phone can do really.
The 1st one is the drilled hole, the 2nd is the current stripped screw.
Otherwise it's probably just that you've overtightened them or crossthreaded them when you last reassembled it. If they were fine when you got them, it's probably not a bad tap during manufacturing. Depending on how much material is left around the newly drilled hole, you might be able to tap it yourself and fit a bigger screw to fix it. For the one you haven't drilled out yet, I would keep trying to unscrew it as long as your screwdriver is not camming out. Sometimes a tap on the back of the screwdriver with a hammer can help, but that risks damaging your tools and/or the case, so it may not be good advice...
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