How would you rule on removing worn items from a target?

[kbob]

So I was running a one shot over the weekend and the players were fighting a demon that could fly. One of the players had boots of flying. Having Int in the upper teens and being a demon (and old) I thought it was appropriate for him to surmise that the flying, half-orc Ranger was flying based on his boots. So after the Ranger flew up to attack and damage the demon (which he did a pretty good job on), the demon decided to “disarm” the boots. I used the disarm action from the DMG. Once removing a boot (both must be worn to work) the player dropped. I should state that I had no doubt in the players overcoming this challenge with no casualties. They eventually killed it and felt accomplished. That said, afterwards, I think I was too liberal on that ruling. I just did so on the fly as I wasn’t planning on the demon taking such an action. No one complained or seemed to be jilted. The player kinda shrugged and nodded that it made sense for the demon to do so and went with the disarm rule. However, I think maybe he should’ve had the Ranger at least grappled first and maybe even do a disarm attempt with disadvantage. Looking back, that makes more sense to me. I may do this going fed if an occasion arises. Also, not allowing attempts to remove worn items from targets larger than self. What are your thoughts?

[Naanomi]

I usually use the grappling system for anything not held, requiring a successful grapple established to try (though I would play around with this when trying to say... Strip a ring off a giant or something) and then further checks (with advantage/Disadvantage depending on how well it is attached and other factors) to actually remove it

[quindraco]

So I was running a one shot over the weekend and the players were fighting a demon that could fly. One of the players had boots of flying. Having Int in the upper teens and being a demon (and old) I thought it was appropriate for him to surmise that the flying, half-orc Ranger was flying based on his boots. So after the Ranger flew up to attack and damage the demon (which he did a pretty good job on), the demon decided to “disarm” the boots. I used the disarm action from the DMG. Once removing a boot (both must be worn to work) the player dropped. I should state that I had no doubt in the players overcoming this challenge with no casualties. They eventually killed it and felt accomplished. That said, afterwards, I think I was too liberal on that ruling. I just did so on the fly as I wasn’t planning on the demon taking such an action. No one complained or seemed to be jilted. The player kinda shrugged and nodded that it made sense for the demon to do so and went with the disarm rule. However, I think maybe he should’ve had the Ranger at least grappled first and maybe even do a disarm attempt with disadvantage. Looking back, that makes more sense to me. I may do this going fed if an occasion arises. Also, not allowing attempts to remove worn items from targets larger than self. What are your thoughts?

1) I wouldn't let the demon realize the boots were doing the flying without detect magic or similar - in general, there are myriad ways to fly, including myriad ways to fly magically. That half-orc ranger could have have a Genie dip, for example.
2) Disarm has disadvantage from holding something in two hands, let alone being actually worn. I would say you can only remove someone's boots with Disarm if you knock them prone first, and then you have Disadvantage on the disarm attack regardless of your target being Prone.

[kbob]

1) I wouldn't let the demon realize the boots were doing the flying without detect magic or similar - in general, there are myriad ways to fly, including myriad ways to fly magically. That half-orc ranger could have have a Genie dip, for example.
2) Disarm has disadvantage from holding something in two hands, let alone being actually worn. I would say you can only remove someone's boots with Disarm if you knock them prone first, and then you have Disadvantage on the disarm attack regardless of your target being Prone.

I omitted some of how he came to that conclusion for brevity sake. The Boots have wings on them and are certainly the most flashy item he has besides his weapons. So I did an arcana roll that I thought was appropriate. He’s not stupid and it made sense. It’s very probable he can even across something like that in his centuries of life.

That said, I hear your point about being prone. This is something I can chew on and think about.

[noob]

I omitted some of how he came to that conclusion for brevity sake. The Boots have wings on them and are certainly the most flashy item he has besides his weapons. So I did an arcana roll that I thought was appropriate. He’s not stupid and it made sense. It’s very probable he can even across something like that in his centuries of life.

That said, I hear your point about being prone. This is something I can chew on and think about.

Would the demon have tried to steal the boots had they been identical looking but not magical and that the fighter had been flying another way?

[kbob]

Would the demon have tried to steal the boots had they been identical looking but not magical and that the fighter had been flying another way?

Probably yes. I mean wing boots are uncommon magic items. So it’s not like they are extremely rare to find. Also If he had boots with wings on them and he was flying somehow, and If I knew nothing about DnD games or even if I was in a real fantasy world setting that would be my first guess.

Regardless that has little to do with the intent of my post.

[noob]

How hard would it be to dismember a foot therefore removing the boot with it?

[Temperjoke]

It sounds like a reasonable assumption for the demon to make, given what you've described. I might have gone with grappling, as someone else mentioned, given that boots are typically more securely fastened than a held weapon.

[Valmark]

The ruling was likely the correct choice (or one of them) since the players had fun regardless- that said I probably would've gone with grappling too. Mostly because Disarm seems meant for held stuff.

Maybe make it two Athletics checks- one to grapple and one to remove the boots. I'd let a creature with multiple attacks to substitute two attacks to make them in a single round.

On another note that seems completely reasonable for the devil to assume- wings on shoes for a flying character? It would be suspicious if a character wasn't flying even!

[kbob]

Thank y’all for the replies. I think in the future grappling would certainly need to be part of it.