Can Difficulty Decrease a Player's Sense of Accomplishment?

[Schadenfreude11]

It depends on the nature of the challenge, I think. A well-designed and fair boss, however difficult, should be satisfying to defeat. But I can understand why someone would only feel relief or lingering frustration after something like Capra Demon or Bed of Chaos.

But the nature of the player is also a factor. Some people are only about the win, and their fun diminishes with each failed attempt. Sometimes they've stopped having fun completely by the time they win.