My D&D group is new and we are all still getting used to playing the game and are running through the Starter Set adventure.

During this adventure we end up capturing a Wizard and we bound and gag him. My character being paranoid made sure to attach manacles to him and also to use two different lengths of 50ft rope to ensure that he would not be able to break free. During the return back to town the DM had him keep rolling strength checks against the manacles and rope and one by one he kept breaking through them and I ended up having to borrow the entire party's supply of rope to keep him secure because he kept breaking through them. By the time I was able to deliver him he was wrapped in 200 ft of rope and looked like more rope than man after breaking my manacles and two different lengths of rope.

I know that the rules say that the DC of Hempen rope is 17 but I still think that in any real world sense it is ridiculous to think that this Wizard can Samson his way through each individual rope while also being held by several other lengths of rope and a set of manacles. One would think that the weight of the ropes alone would keep him in check.

I guess my question is that is there any precedent for the DC being raised when you are attaching multiple different factors into keeping a prisoner secure or are you just supposed to roll each rope individually?

Edit: My DM has responded to my post and it looks like I didn't have all of the information originally

"I rolled 2 rolls per day of travel. This was his daily attempt to free himself from his bindings with disadvantage. He got 2 Nat 20's the day he broke the manacles and a 19 & 20 to break free of the rope. His Str modifier is -1, but 18 still clears the rope's DC. He had disadvantage due to the leather armor and sheer volume of rope around him He also had to break the manacles before he could even start trying to work at the rope, since you did put those on him first"


3 Answers 3


He must escape/break-free from each separately

However, there are only 2 restraints present: the manacles and the rope - the fact that you used 2 lengths (or 7 or 15) is irrelevant - you tied him up once.

He only gets one shot to escape and one shot to break each

Your DM was unfair; he was inducing Rolling to failure. The NPC can only attempt to escape from each binding once and only attempt to break each binding once. If he fails he is not agile/strong enough to do it trying again won't make him so unless circumstances change.

Allowing the NPC to do this means that he will succeed eventually (always assuming that it is possible for him to do so) thanks to how "rolling to failure" works out mechanically.

How I would rule it

The manacles have a DC20 Strength check to break and a DC20 Dexterity check to escape. The rope has a DC17 Strength check to break and a are an opposed check between his Dexterity and your Dexterity (Slight of Hand) [Sage Advice]. If you were wise, you would get someone to Help you tie him up to get Advantage.

Being tied up, I would give him Disadvantage on all of these because he is under the restrained condition. (See Appendix A).

So that's 2 chances to get out of each and he has to get out of both to escape.

  • 1
    \$\begingroup\$ I would think there would be some kind of reset, such as 1/day (assuming they never let him out of the restraints while travelling). If it were a PC trying this, I know they'd want more than one or two dice over the course of being dragged across the land. \$\endgroup\$ Commented Feb 14, 2018 at 13:26
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    \$\begingroup\$ +1 for the rolling to failure (success) reference. This was definitely a mistake on the DM's part. \$\endgroup\$ Commented Feb 14, 2018 at 13:52
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    \$\begingroup\$ @Ifusaso: I would not let a PC attempt another check unless as Dale said "circumstances change". There has to be a reason to give them another check. \$\endgroup\$ Commented Feb 14, 2018 at 13:54
  • \$\begingroup\$ Right... I would consider a new day circumstances changing... the character is rested and ready to try again. Personally. \$\endgroup\$ Commented Feb 14, 2018 at 16:03
  • \$\begingroup\$ Is "He only gets one shot to escape and one shot to break each" how you would rule? \$\endgroup\$ Commented Jan 31, 2020 at 3:37

There are no critical successes on skill checks in D&D 5e (See Chapter 7). The problem here is that your DM allowed a creature with -1 strength modification to pass a DC 20 Strength check to break the manacles.
A natural 20 is not an automatic success.
Two checks per day to get out of the rope, with great luck, is reasonable.
You're right that it would be unfair for your DM to allow the NPC to make check after check after check, but two per day while traveling is reasonable!

  • 1
    \$\begingroup\$ Welcome to RPGSE. I made an edit to put some formatting in. You could improve your answer by referring to the DMG's optional rule about critical successes - it is an optional rule, but if the DM is going to apply it they ought to let Players know. Beyond that, please have a look at the tour, help center, How to Ask and How to Answer for how to get the most out of an SE site. \$\endgroup\$ Commented Jan 13, 2021 at 14:08

The DM determines the DC, advantage/disadvantage, and any limitations on retries

Manacles require a DC 20 strength check to break. However in this case a character is not trying to break out of manacles, they are trying to break out of manacles tied with 100ft of rope. How high a DC is required to break out of that is up to the DM, but clearly it should be higher than 20.

Considering the target is bound tightly and gagged, and spending multiple days in this condition, I would expect this constitutes disadvantage if not exhaustion.

Retries are purely up to the DM

While there are no rules preventing making unlimited retries as fast as you can (once ever 6 seconds in combat, more or less often outside of combat depending on the task), there are various factors you should consider.

In many situations there is only 1 opportunity for attempts. If you are trying to spot a lie and fail, you can hardly ask the person to repeat what they just said. If you are trying to pickpocket someone and fail, then they might be on to you.

In some other situations attempts may prevent subsequent retries. If you try to pick a lock and fail your tools may foul the lock or become stuck inside. If you try to forge a signature and fail, you can't just erase the ink.

In this situation the target is sitting there, manacled and tied up. They have plenty of opportunities to attempt to break out. Failing to break out does not prevent future break outs.

But, After minutes if not hours of attempts the target is surely exhausted, the DM may start stacking on exhaustion levels. How long can you stand there trying to tear a piece of rope apart while bound?

Being tied up doesn't exist in a vacuum

So how can you keep someone tied up if they can retry many many times when the only penalty is perhaps getting tired?

Well, there's no need to be narrow minded. As you experienced, those are not the only possible penalties. When the target did manage to partially succeed you managed to restrain them further. You could also threaten to beat them, harass them, or threaten someone or something they care about. These threats are what keeps the target from making attempts.

The DM may decide that the target may also be conserving strength or thinking of another plan. NPCs are smart after all.


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