I do treat it as automatic success for typical thief tasks, but not for atypical tasks. Some tasks may have penalties, which means there's still a chance of failure. Which I guess raises the question: what are the typical thief tasks? I'm a firm believer in thief abilities being slightly unnatural, not just mundane skills that anyone can learn. Here are the Greyhawk descriptions, and my expansions in emphasized text.
- "open locks by picking or foiling magical closures"
- Emphasis added. Original ability was not mundane, no need to expand.
- "remove small trap devices (such as poisoned needles)"
- Anyone can learn to remove small traps (5+ on 1d6 chance,) but failure triggers the trap. Thieves get a bonus on the roll.
- "listen for noise behind closed doors"
- Anyone can do this, but thieves have better odds and improve at it.
- "move with great stealth"
- This is total silence; it is impossible to hear the thief if the roll succeeds. Otherwise, the thief has normal surprise chances. Lasts until the thief does something that might change this (pick up something that could make noise, or deliberately make noise.)
- "filtch items and pick pockets" [sic]
- Learnable by anyone, but thieves get really good at this. Subtract 1 point if the victim is higher level.
- "hide in shadows"
- Anyone can hide behind an object, but only thieves can hide "in plain sight" with nothing but shadows as cover. Remains hidden until thief decides to step out of shadows or a different kind of vision makes the thief obvious; if the light changes but there are still shadows, thief gets a new roll to remain hidden.
- "strike silently from behind"
- Expand to any surprise attack.
- "climb nearly sheer surfaces, upwards or downwards"
- No equipment needed, must have at least tiny cracks. Non-thieves can normally only climb with equipment. 5+ on 1d6 roll is for failure, not success; subtract hit dice from roll. Add 1 point each for slippery or crumbling surface.
- Remove small magical trap (not area traps)
- Hear a whisper in the same building
- Disappear into shadows while being observed
- Climb perfectly smooth surface (glass)
