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

My personal issue with 'just trying again', is that it removes any real challenge.
And yet this system is used for combat.

If you allow to try again infinitely, the player can just keep rolling until they finally roll a 20.
Increase the stakes with each additional attempt.

Attempt to Lockpick
Increase the time (1 minute, 10 minutes, 20 minutes etc) with each attempt and roll for a Random Encounter every hour or less depending on traffic in that area.
Also every attempt increases the risk by 15% that the lock becomes jammed or the lockpick breaks

Attempt to Persuade
Have the DC increase by 5 with each attempt and when it first reaches 20 or more.
You feel that you've done all you can do, one more attempt may indeed anger the person.
Difficulty increases bya further 5 (now Dc 25) and failure is not limited to just failure but you risk damaging any future discussion with the person (i.e. you have DisADV on any social rolls with this person).

Attempt to Climb a Wall
First attempt fails, additional attempt requires exertion.
Success with a Cost - Lose 1 HD
Failure by 5 or less - You succeed but tear your glove/boot/rope in the process and lose 1-2 Hit Dice.
Failure by 6-10 - As above, and earn a level of exhaustion (disADV on physical checks) which can be recovered with a short rest
Failure by 11+ - As above, and you suffer a twisted ankle (movement halved) which requires a long rest to recover from.
 

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For the me best a character tries is represented by his ability score plus proficiency score. The dice represent the external circumstances, luck, the weather whatever.
Yes, in other words, the current conditions. When I say the roll is the best the character can do under the current conditions, that takes in all three factors, because all three numbers are added together.

For me a character doesnt' need to change something or at least nothing meaningful. In case of opening a door I would be satisfied with "I try a different angle with my lockpicking tools", but IME for DMs with your style this would be NOT enough.
Sometimes I allow this, if it makes sense for the situation. It at least adds some roleplaying flavor to the scene, which is part of the goal.
 

And yet this system is used for combat.
It's not. In combat, the challenge is in trying to get the enemies HP down to zero before they do the same to you. There is no such mechanic in something like trying to 'pick a lock' : it's not as if the lock gets 'slightly more picked' upon each attempt, resulting in a 'fully picked lock' in X attempts.

Also every attempt increases the risk by 15% that the lock becomes jammed or the lockpick breaks
Which leads to the end-result of an 'unpickable lock', which is quite different from what I stated: 'just attempt it enough times until it succeeds'.
 

If it's within their ability (DC isn't too high to achieve) and there's no cost of failure (plenty of time, no wandering monsters, etc), then yeah, they should succeed without rolling. It's not and shouldn't be a challenge.
But if you can just pick a lock without the chance of failure, then why have a lock on the door in the first place ? You might as well leave it unlocked ?
 

But if you can just pick a lock without the chance of failure, then why have a lock on the door in the first place ? You might as well leave it unlocked ?
The "within their ability" bit in what you quoted is important. Someone put the lock on the door or chest to stop people of X ability or less from getting in. Chances are, they also had sentries or other guardians.

Also, it is worth remember that this is a game and sometimes a lock is there for a purely gamist reason.
 

The "within their ability" bit in what you quoted is important. Someone put the lock on the door or chest to stop people of X ability or less from getting in.
Ah. I missed that, thanks for pointing it out. So let me see if I understand that correctly. If (in the lock picking example) they have thieves tools, and are proficient with it (or other + plusses), they will be able to unlock a door with a DC of 10 without rolling, but with a DC of 17 they have to roll ? (giving them the chance of luck to open it, but it is not as likely ?)
 

Haha. I get it. But surely you have a rogue stabbing and hiding or stabbing and disengaging? Surely you have a wizard that is surrounded that needs to get out of there? Surely you have a fighter that has to reposition in order to grant advantage to another PC attacking? And, you can still move, in fact you can move 35' around a large creature, without provoking opportunity attacks.
No, because all the Rogue has to do is attack a creature adjacent to an ally and they can Sneak Attack. Or give themselves advantage with a bonus action for a ranged attack. The only time you'd have to try the Stealth thing is if you wanted to Sneak Attack a creature in melee and you were by yourself. My groups have learned that spreading damage around instead of focus firing causes combats to take forever. As for circling around a creature, sure, you can do that, but there's often no reason to do so. It's not that it never happens, but without any bonuses for changing position (like d20 flanking), there's normally no particular reason to do so. This may change in my current group, which may soon be adding a Paladin, so there might be some jockeying to remain in their aura.
Why do we gate ability checks? Again, they are all unique, so, some get gated and others don't. But there are a few core reasons why:
  1. To keep the game moving. It is an expectation in D&D that combat takes quite a bit of time. (With four players and a DM, 1 round - 6 seconds, can take 15 or even 30 minutes of real time.) Exploration, the expectation is not the same. Hence, why so many rules revolve around combat, and fewer around exploration.
  2. Logic dictates. Reading an ancient book, and failing your history or arcana roll, and therefore not understanding it, is kind of a done deal for that scene. Trying to remember something about a long lost, dead god, and failing on your religion roll, is kind of a done deal for that scene. (I do not know of any DM that would disallow a later roll after doing research, speaking with sages, etc.)
  3. And we gate to sometimes hit a punchline or set a scene. We once had a character named Caz Creekleaper. His first attempt to cross a river, he rolled a 1. He was swept downstream and plummeted over the falls after failing a strength check to grab on to something. It was classic. It was almost destiny. That punchline was perfect for a fun laugh. (He was laughing too.) Sometimes, the failed roll just sets the scene, for serious or comedic effect.
And, I still think the door example needs to not be the only point. Everyone that has responded to the "breaking down the door" has stated they give repeated chances. And if they don't, I bet they would if you brought an axe to the door and performed the whole "Here's Johnny" bit. ;)
Change out opening a door for searching a room, finding a secret door, locating an invisible enemy, tracking foes, or finding a path through a dense jungle. In previous points I disputed one and done Knowledge checks as well, because who hasn't blanked on recalling something, only to suddenly later go "Oh! Duh! It's x!". Also, I mentioned physically destroying the door in my last post as what my players tend to do if they encounter a door that cannot be opened (ala 2024 Arcane Lock). The whole reason I keep circling back to the door is my own experiences with my own front door, that occasionally refuses to open for me without effort and how silly it would be if every time I failed to open it, I was immediately forced to call a locksmith or take an axe to it.*

*Someone did reply to that saying that maybe multiple attempts were all one check, but 5e doesn't delineate any difference between in and out of combat actions, that's something individual DM's add to the game. Opening a door in combat would take an action, no action, or a bonus action (for a Thief), depending on circumstances. To say that one check = several combat rounds is within a DM's right to determine, but I don't believe we have any concrete examples of this from the rulebooks (I could be wrong!), so all we have is while DM A might say opening a door takes 30 seconds, DM B might say a minute, and DM C might say as part of a 6 second round.

I'm not saying there aren't justifications for this- a Charisma check after a conversation could take several minutes to account for said conversation. But there's no standard amount of time that I think everyone could agree upon. I mean, going back to lockpicking, modern locks are probably more complex than D&D locks (or should be- dungeons always seem to have complex clockwork death traps with no real justification for their existence, that work perfectly despite years of neglect and corrosion, lol) yet you can easily find Youtube videos of people showing you how to open one in very short amounts of time.

I think 4e defined searching a room, bandaging wounds, taking a drink or nomming on some rations to be ~5 minutes, as justification for it's short rest periods, which is generally the length of time I go with. But if a character had the ability to Search as a bonus action, I'd have to take that into account.

Ditto for Hiding. In real life, finding the right spot and hunkering down in it probably could take a good 20 seconds, but the game assures us that it can be done much more quickly (and any goblin can do it as a bonus action).
 

Ah. I missed that, thanks for pointing it out. So let me see if I understand that correctly. If (in the lock picking example) they have thieves tools, and are proficient with it (or other + plusses), they will be able to unlock a door with a DC of 10 without rolling, but with a DC of 17 they have to roll ? (giving them the chance of luck to open it, but it is not as likely ?)
I think what @billd91 was saying was that if they PC could conceivably do it with a roll (the DC is less than 20+the PC's modifiers) and there is neither danger nor time constraints, they can just do it. Basically the old Taking 20 rule.
 

Sounds like you should run your combats like a skill check: one roll decides it. At least it would be over faster.
Lol, it might! I try to make my combats more dynamic- for awhile I used Lair Actions a lot when they encountered enemies in, well, your Lair. But it turned out to be just one more thing for me to keep track of and I'd often forget about the Lair Action lol. Sunday there was a long battle with 7 Grimlocks, 6 standard and their CR 2 leader (not D&D, but ToV, which has made monsters more complex and nastier). There was supposed to be a Lair Action (a magical mishap due to an ancient magical device the Grimlocks worshiped as a deity), but by the time I remembered it, the fight was going overlong as it was. The party Fighter decided to block the doorway, as it was only 5' wide, and thus was being pelted with attacks while the other three characters had to shuffle in and out of the squares behind him to make ranged attacks. In the end, I forced movement by grappling the Fighter and dragging him into the cave, otherwise, the whole fight would have went on that way until they slowly whittled the Fighter down (and thanks to a 20 AC, that was taking awhile).
 

I think what @billd91 was saying was that if they PC could conceivably do it with a roll (the DC is less than 20+the PC's modifiers) and there is neither danger nor time constraints, they can just do it. Basically the old Taking 20 rule.
Thanks for the response. I was unaware of the 'Taking 20' rule (I'm new to D&D). But doesn't all of this mean that you are taking the randomness out of the game ? I mean, you are constantly rolling dice at random. Which to me, means that even though the PC's stats are really good you could still fail (you have a bad day), or even tough the stats are bad you can still succeed (you got lucky) ? I kind of like that randomness if I'm honest.
 

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