It's been my experience that when the locks get really dry inside, the key stops going in as far as it needs to to trip all the tumblers. What I normally do is saturate the key with graphite lubricant (or a lite oil of some kind) and move it in and out of the lock until everything inside gets coated. The key should go all the way in after that. If not, they cylinder may need to be disassembled to find the tumbler problem.
The only other idea I have is that the teeth on the key have become worn, and don't activate all the tumblers like it did when it was new. If you have a spare key that you rarely use, try it to see if there's any difference.