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I am a new DM, trying to understand the magic of the Portable Hole. I've read through as many previous posts on Portable Hole shenanigans as I could, but none seem to answer my questions. One of my players has managed to find a Portable Hole, thanks to the random loot tables. He's familiar with them due to having played earlier versions of D&D. I, having never played these versions, am not as familiar. We find ourselves at odds on just how this item works. In order to keep this post short, I won't post my interpretation of the rules, though suffice to say I disagree with the following.

  1. The Portable Hole can be opened by two people, holding it open like a sheet.

  2. If even the smallest portion of the cloth is opened, the portal is opened and the character can reach into the extra dimensional space.

  3. The Portable Hole can be thrown upwards, and unfold on its way back down, therefore opening the portal.

Do the rules shed any light on these complicated questions?

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  • \$\begingroup\$ It is possible that the player may be inspired by how the Forgotten Realms character, Jarlaxle makes use of the one he stores in his hat. \$\endgroup\$ Commented Sep 26, 2023 at 20:52

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RAW rules indicate the negative for all of those possibilities

The Portable Hole can be opened by two people, holding it open like a sheet.

No, it can not. The portable hole(DMG, 185) states with my emphasis:

You can use an action to unfold a portable hole and place it on or against a solid surface, whereupon the portable hole creates an extradimensional hole 10 feet deep.

Only one person can open the portable hole, whoever has it must use their action. It's also important to note that the second part of the sentence dictates that the extradimensional space doesn't open until it's been unfolded and placed on or against the surface.

If even the smallest portion of the cloth is opened, the portal is opened and the character can reach into the extra dimensional space.

This question also suggests a means of opening the hole that isn't listed in the description. The only RAW way to use the portable hole is for a single character to use their action to unfold it completely on or against a solid surface.

The Portable Hole can be thrown upwards, and unfold on its way back down, therefore opening the portal.

For your final question, please refer back to the original quote on the portable hole mechanics in that the item must be placed on or against a solid surface. Throwing it up in the air is not placing it on or against a surface. Yeah, it'll eventually maybe fall down and land on one, but that's not placing it. It also doesn't turn into the access to the extradimensional plane until it's unfolded and on or against the surface.

A note on clever uses

None of the above means the players can't figure out ways to be clever with this, including asking to use Help so that more than one person opens the Hole - it just means they need to try and be clever within the constraints of how to use it.

Of course, you as DM may opt for more freedom in how to use it, but if you're asking about the RAW constraints, these are what we've got.

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    \$\begingroup\$ Things I have used a portable hole for... had a portable lab set up, one of my players had one as a garage to store his cart, another had a platoon of skeletons stacked in one, one completely filled with water \$\endgroup\$
    – Slagmoth
    Commented May 5, 2020 at 2:44
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    \$\begingroup\$ Regardless of if two people can open it together, holding it open like a sheet is definitely not how it works per RAW. The extradimensional space does not appear until the hole is placed on or against a solid surface (and at least one person would have needed to use an action to do so). \$\endgroup\$
    – smbailey
    Commented Sep 26, 2023 at 23:22
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RAW prohibit nearly all of those possibilities

NotArch's answer is great, and clearly demonstrates why nearly all of the claims made by OP's player are incorrect. However, there is one point on which I think it has overreached.

OP's player states that "The Portable Hole can be opened by two people, holding it open like a sheet," whereas the description of the portable hole says:

You can use an action to unfold a portable hole and place it on or against a solid surface, whereupon the portable hole creates an extradimensional hole 10 feet deep.

NotArch correctly states that "It's also important to note that the second part of the sentence dictates that the extradimensional space doesn't open until it's been unfolded and placed on or against the surface." However, their answer also says "Only one person can open the portable hole, whoever has it must use their action."

When the portable hole description says that one person can open the hole, this is not the same as saying that only one person can open the hole. RAW the hole must be opened by at least one person, and that minimum person must use their action to do so. But nothing in the rules either permits or prohibits two (or more) people from opening a hole. Lest this point be considered mere pedantry, consider that some of the most fundamental actions in the game, attacks and ability checks, have rules describing them in terms of one person making an attempt, but are also subject to the assistance of a second person through the Help action.

The second person assist

In Making an Attack we can read:

When you make an attack, your attack roll determines whether the attack hits or misses.

But in Help we also see that:

Alternatively, you can aid a friendly creature in attacking a creature within 5 feet of you. You feint, distract the target, or in some other way team up to make your ally's attack more effective. If your ally attacks the target before your next turn, the first attack roll is made with advantage.

Making attack uses the same (singular) 'you' language as the hole - and yet your attack can be assisted by another person.

Similarly, making an ability check is described as something that a singular character does:

An ability check tests a character's or monster's innate talent and training in an effort to overcome a challenge.

But in Help we also see that:

You can lend your aid to another creature in the completion of a task. When you take the Help action, the creature you aid gains advantage on the next ability check it makes to perform the task you are helping with, provided that it makes the check before the start of your next turn.

And in Working Together we find:

Sometimes two or more characters team up to attempt a task. The character who's leading the effort--or the one with the highest ability modifier--can make an ability check with advantage, reflecting the help provided by the other characters.

It is clear that even though the rules describe actions as being performed by a single character, as a general feature those same actions can be assisted by other characters. The rules for opening a portable hole say only that one character opens the hole, and must spend their action to do so; the hole rules neither permit nor prohibit another character from assisting in that process. DM's should certainly be cautious of 'the rules don't say I can't, so I can' arguments. But in this case, the 5e rules generally provide ways for a second character to assist a first in some action, and it is a reasonable assumption that a second character could assist the first in opening the hole, so long as all of the explicit rules of the opening the hole are met.

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