D&D 5E (2014) Can you retry a failed skill check? How long?

[Misanthrope Prime]

I know I'd be a bad parent because my philosophy as a DM is "a skill check represents you trying your best: your best wasn't good enough". If you think you can get a 20 on that theives tools roll to unlock the door, then you shoulda thought of that before you rolled the dice the first time.

The only exception I'll make is if your "best" mechanically changes: if you're under the effect of a buff that changes your aptitude in that arena, or you've since leveled up and gotten better and more practiced at that skill.

 

[Scott Christian]

The main area where I have different DCs in mind is with knowledge checks. You may recognize a holy symbol of Set automatically, a DC 15 and you realize it's not the standard version you've seen before, a DC 20 and you recognize what's different about it and get an idea of what it implicates and so on.

Yes, I have written that into adventures for key knowledge checks. For example, a simple history success gives them x knowledge, but a hard history success gives them x + y knowledge, and an epic success grants them x + y + z knowledge. If you have the time to do it for adventures, I find it very beneficial.

 

[jayoungr]

my philosophy as a DM is "a skill check represents you trying your best: your best wasn't good enough".

I do something similar but with a variation: I say "The skill check represents your best attempt under the current circumstances. If you want to try again, you'll have to change something to give you different odds." Depending on what they come up with, I might give them a bonus to the second roll. (Saw this idea online somewhere, but I can't remember where now.)

 

[James Gasik]

It's interesting that in the game, attacking an enemy and missing, but being allowed to attack again, even though the circumstances (your offense skill and their defense skill) are unchanged is perfectly cromulent, but trying to force open a door makes some people go "well, you gave it your best shot, but you can't open this door unless you come up with a better approach".

 

[Misanthrope Prime]

It's interesting that in the game, attacking an enemy and missing, but being allowed to attack again, even though the circumstances (your offense skill and their defense skill) are unchanged is perfectly cromulent, but trying to force open a door makes some people go "well, you gave it your best shot, but you can't open this door unless you come up with a better approach".

The door doesn't get to try to force you open in return, unless it's a mimic.