Interesting issue. I make some gadgets that use either a Beagle Board (old) or Beagle Bone (newer) for a net interface. These run in a rack that supplies +6 V power, so I use an L4941 low dropout regulator to provide the +5 for the Beagles. These have run fine for several years. Now, a couple of them started crashing the Beagles every few minutes.
Well, on some of these units I did not heat sink the regulators. The Beagles, when idling, draw 250 - 300 mA, with a 1 V drop from 6 V down to 5 V, that should be 250 - 300 mW. The L4941 is rated at 50 C/W junction to ambient in frree air, if I read the data sheet correctly. (Maybe they are playing with numbers in the datasheet and it really doesn't mean "free air".) Anyway, some checks I did when first setting these up seemed to indicate this was reasonable, as the regulators didn't get over about 40 C after a long run.
Anyway, bolting the existing regulator to the aluminum equipment case fixed the issue. So, either the regulators got more sensitive to temperature, or the thermal conductivity changed, or something. I've never see this before.
Jon