First time that happened to me was on a bike tour about a decade and a half ago, with a 50mm wide tire which of course takes a lot of air when I pump it up the second time, with a small portable pump.

Since then, I always use a wrench to tighten the valve core. Have not had a problem with that since. And I usually use the Lezyne pump for bike touring which uses that chuck.

Several years ago I saw a great sale on Schwalbe tubes, bought a bunch of them and they all had removeable cores. On that batch I added just a tiny bit of blue (removable) thread locker to the valve cores before I tightened them with a wrench. If you try this make sure that no threadlocker gets onto the valve seat.

Last year I saw some valve caps that had a small hole in the cap that fit over the wrench flats on a Presta Valve. Bought several of those caps to put one on each of my bikes. Thus, the cap also functioned as a wrench to tighten the valve core.