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Based on this question: Does the Aspect of the Moon Eldritch Invocation effectively allow for unending Wild Shape?

In that question the OP is wanting to know if they could keep regaining use of wildshape to stay in wildshape for a week of downtime. Perpetual state of resting to me means that each hour of downtime would count as the end of a short rest or each 8 hours spent in downtime as the end of a long rest.

Is it possible to be in a perpetual state of short/long rest whether during downtime or not for the purpose of regaining class/racial features?

In other words: Can a PC use 16 short rests then an 8 hour long rest each day and continuously regain features that replenish on short rests?

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Long Rest - One per Day.

The question was restated to articulate you didn't mean long resting all day, but I will leave this here for other searches.

The rules for a long rest state that you can only benifit once per day. That means that while you don't need to sleep you still can only long rest once.

A character can't benefit from more than one long rest in a 24-hour period, and a character must have at least 1 hit point at the start of the rest to gain its benefits.

Short Rests - Yes, But Why?

I suppose, as long as you only do "light activity" which is defined as:

nothing more strenuous than eating, drinking, reading, and tending to wounds

you could spend the downtime chilling in bed -- binge watching the midevil fantasy world equivalent of NetFlix, or reading. But, what does that get you?

A character can spend one or more Hit Dice at the end of a short rest, up to the character's maximum number of Hit Dice, which is equal to the character's level. For each Hit Die spent in this way, the player rolls the die and adds the character's Constitution modifier to it. The character regains hit points equal to the total (minimum of 0). The player can decide to spend an additional Hit Die after each roll. A character regains some spent Hit Dice upon finishing a long rest, as explained below.

After the hit dice are spent, or you're at max health, and spell slots replenished, what is to be gained? You could cast all your spells, and begin resting again I suppose.

The DM Can Stop You

The DM has final say at everything at the table. They can say, "Your rest is interupted by a noisy person in the room next door," or simply "No." The DM might see this kind of hack as an abuse of the rules, and can either amend or ignore the rule to keep balance at the table.

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    \$\begingroup\$ But that edit works for me. +1 It's also unclear as to whether or no the adventuring short rest/long rest mechanics are active during downtime. \$\endgroup\$ – NautArch Mar 4 '20 at 17:48
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You can be in a perpetual state of resting, but you can't be adventuring during that time. Presumably the reason you're playing D&D is so that you can go adventuring, so perpetual-resting is impractical except in theorycrafting.

Also, please note that an eight-hour long rest would mean no regaining wild shapes for eight hours. So you'd need to be an eighth-level druid to maintain wild shape for the full long rest (four hours per wild shape). If you're an eighth-level druid, then you could just take a short rest once per eight hours and you'd also be able to maintain wild shape indefinitely.

See also this question about the theoretical "coffeelock" character which gains spell slots by short-resting.

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