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I have a wizard who has a Pearl of Power. According to the rules, it looks like he should be able to, on each day, take a short rest to attune to it, use it to recover a spell slot, then take a short rest to re-attune to his usual other magic item. This seems to me kind of a weasel workaround to effectively get attunement to 4 magic items, but looks legal. Is there any reason (other than time management) that this doesn't work?

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Well, it'll take four short rests, not two, but otherwise, yes, this works.

An item can be attuned to only one creature at a time, and a creature can be attuned to no more than three magic items at a time. Any attempt to attune to a fourth item fails; the creature must end its attunement to an item first.

So at the start of the day, the wizard has to end his attunement to one of his other items before he can attune to the Pearl of Power. Similarly, after using the Pearl, the wizard can't just attune to the other item; he has to end his attunement to the Pearl first.

A creature’s attunement to an item ends if the creature no longer satisfies the prerequisites for attunement, if the item has been more than 100 feet away for at least 24 hours, if the creature dies, or if another creature attunes to the item. A creature can also voluntarily end attunement by spending another short rest focused on the item, unless the item is cursed.

And in order to end his attunement, he has to:

  • Not be a spellcaster, which is basically impossible.
  • Keep it more than 100 feet away for 24 hours, which breaks the point of this.
  • Die (Yikes!)
  • Have another creature attune to the item in question. This could work, but it'd require them to spend a short rest, so he'd have to wait 1 hour and then take his short rest to attune to the other item.
  • Take a short rest himself.
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  • \$\begingroup\$ I think it might be possible for 1 player to attune to another's item and that player to attune to a new item during the same short rest, depending on how the DM rules on the exact timing of (1) number of attuned items check and (2) attunement completion. If (1) and (2) happen at the same time, the other player can start their attunement 1 min earlier so that as the attunement comes to an end, they have just been reduced to 3 items (so 2 rests). Although, since this is a little on the abusive, but legal side of things, I am okay the idea that it should be the harder option when ambiguous. \$\endgroup\$ – Nick Brown Dec 6 '17 at 15:58
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It is completely legal. He could even use several pearls of power every day.

The limiter is the availability of 1-hour intervals where he can do the attunement.

Adventurers often don't have the luxury of choosing their schedule. This particular DM not-so-often pulls quantum ogres from his hat to derail the R&R of the party. An adventure should keep the adventurers on their toes.

And he needs an extra 1-hour interval to de-attune before reatunning with another item.

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