When is it appropriate to allow/disallow players to re-roll skill checks?

For instance, a player walks into a room in a dungeon and rolls a 2 on perception. Do I allow them to re-roll? If so what's the point in rolling and not just telling them everything the moment they walk into the room.

The players I have always try to roll again and again, I have no problem with them checking around again, but at what point do I have them take a 10 or a 20, and how do I do that organically?

My question isn't about things that are actively in action, but more about those rolls when nothing is happening. Like if the group is wandering around a dungeon, and stumbles into a room. How do I handle the perception check for a secret door? Or a rogue hiding? Things that don't have an obvious repercussion, unlike failing to pick a lock.


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