Content of the article: "How do you handle reattempts at ability checks? When do you personally allow rerolls, vs when do you not?"
Normally, I run games with this simple mindset, when it comes to reattempting ability checks: "When you make an ability check, you cannot reroll it until the circumstances substantially change." Meaning, if the PC rolled a 5 and failed to unlock a door, they couldn't reattempt over and over again until they rolled a 20. However, if the circumstances changed, like they got new fancy magical tools or they leveled up, then they could attempt it again.
This system has worked well for me, and I think it makes sense. A d20 roll, in game, is more than a check of luck. It's an abstraction of how difficult this specific situation was. Rolling a low number isn't always saying that you failed to unlock a door because you did poorly, it's sometimes saying that this one lock was just really well made. Which I why I (usually) don't allow rerolls unless the situation changes.
This has led to, on a few times, some… weird results, though. Which is why I'm asking for feedback, both on the general principle or when to allow reattempts, and on this specific example.
In game recently, the team rogue failed to unlock a door. So, that's that, you can't just keep trying over and over until you roll a 20. The lock was too much! The team caster used Enhance Ability (Cat's Grace) on the rogue, to let her try again. I figured, sure, why not? After all, a spell slot was wasted, the situation has changed, reattempting the lock makes sense now. After all, this is no longer just the rogue trying to break the lock, it's the rogue being powered by a God. The rogue rerolls with advantage, and succeeds.
After the game, though, I was thinking… This is sort of odd, no? The rogue rolled 3 times on this lock. Once normally, and twice due to advantage on the Cat's Grace. If she had been under Cat's Grace initially, though, then by my own rules I would most likely say she can't attempt the roll after the spell ended. So, in a weird way, I was rewarding the players to use a spell slot, but only after they had failed once.
The players aren't abusing this system, I just found it a bit weird. By using Cat's Grace 2nd, they got 3 rolls, but if they used it first, they would have only gotten 2 rolls.
So, what's your take, not only just on this example, but on reattempting rolls in general. I know older systems had a "taking 20" system where in low stress situations you could simply force a natural 20, but that system isn't in 5e. What do you all do? Do you agree with my rulings? Disagree? I'm interested!
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