I never noticed it growing up but I see it now, TOS is profoundly flakey. My ST has a TOS 1.62 ROM built in and it does not play nice with hard drives.
There’s a simple solution to this, use the wonderful open source EmuTOS instead. Now I’m not resourceful enough to go writing EmuTOS to a flash ROM but my ST does have enough RAM that I can easily get away with loading it up from the hard drive.