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My ship was being boarded specifically from the ship's back by grappling hooks, and then pirates started to climb up ropes to get up to our ship. I asked my DM if I could cast the grease spell on the ropes to make the pirates fall prone, falling into the water. My DM ruled that it did not work.

Should my plan to cast grease on the ropes to make the pirates fall work as I intended?

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Rules-As-Written: Nothing happens

The rules for the spell state that the ground is covered in a slippery substance, and that it confers Saving Throws against falling prone for creatures in the area. It doesn't say anything about being applied to objects or, per your example, ropes used for climbing, nor does potentially being knocked prone have an effect on creatures who are clinging to a rope.

Slick grease covers the ground in a 10-foot square centered on a point within range and turns it into difficult terrain for the duration.

When the grease appears, each creature standing in its area must succeed on a Dexterity saving throw or fall prone. A creature that enters the area or ends its turn there must also succeed on a Dexterity saving throw or fall prone.

Grease, Player's Handbook, pg. 246

It's probably necessary for the DM come up with an explanation of what should happen in this situation

Personally, as DM, I don't think I would approve of simply saying "nothing happens". This is a clever use of a spell in a manner that the rules aren't designed to accommodate, so I think it's appropriate to allow it to have some kind of effect. In this context, I would likely allow 10' of rope to be covered in grease, and for creatures that try to climb across it, I would force them to make Dexterity Saving Throws to stay affixed to the rope.

But that is, ultimately, a DM's call, and there's no twisting of the game's rules-as-written to permit this kind of use.

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    \$\begingroup\$ For the sake of argument, the Grease spell says it make the terrain difficult. In PREVIOUS edition, it used to make 'victims' fall down, but not anymore. Then, there is a very clear rule for climbing ... basically, every movement done while climbing (or swimming and crawling) cost double, or triple if it is in difficult terrain. In other words, they would not fall down if using RAW while allowing grease on a rope, it would just make it so it takes a longer to climb. \$\endgroup\$ – Catar4 Jul 25 at 20:37
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The description of the Grease spell is very specific about the area of effect:

Slick grease covers the ground in a 10-foot square centered on a point within range and turns it into difficult terrain for the duration.

It covers the ground. A DM sticking to RAW would tell you that you cannot cast it on a rope or other object, you can only target the ground.

Me as a DM, would personally allow it to target one object such as a rope.

So what should happen is that no matter what your DM decides to do, you should respect his/her decision.

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