Do you ever run a die over the bolts you remove from your calipers? It’s a good idea to. I’m not sure when my calipers were last removed but the bolts squeaked when I removed the bolts and there was some corrosion and I imagine aluminum stuck in the threads. If you try to force that bolt back in the hole, even if you use anti-seize, you risk deforming the threads, removing more aluminum from the softer caliper and carrier or, worst case, you can strip the threads.
I was reattaching the radiator hose fitting that houses the coolant temperature sensor and even with anti-seize one bolt threading back into the head didn’t feel right—too much resistance. I checked the bolt threads and they were clean. So I gently ran the correct tap into the head and then blew out the hole with compressed air. The bolt felt much better going in. I didn’t snug the bolt up too tight as that fitting has an o-ring and I don’t want to risk stripping anything.
I’m not perfect though. I was putting the rear brake caliper back and cross threaded one of the bolts. Still have to helicoil that hole.
