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If characters have been interrupted during a long rest, do they need to wait 24 hours before taking a long rest again? The rules specify that only one long rest is allowed in 24 hours but it also states they must start over. Which is it?

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No

"One long rest is allowed in 24 hours" isn't true. Characters can perform as many rests as they want. But benefits of a long rest are available only once per 24 hours (see Player's Handbook, Chapter 8, under "Resting"):

A character can't benefit from more than one long rest in a 24-hour period

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    \$\begingroup\$ It's worth noting directly that you get any and all benefits of the long rest only at the end of a successful one. \$\endgroup\$
    – Mołot
    Commented Sep 25, 2022 at 21:20
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    \$\begingroup\$ Even if "One long rest is allowed in 24 hours" was a rule, I think the answer to OP's question would still be the same, since an interrupted long rest is no long rest at all. After all, the long rest is considered to have happened only once it's been successfully completed. \$\endgroup\$
    – Kryomaani
    Commented Sep 25, 2022 at 23:22
  • \$\begingroup\$ I understand we probably aren't recommended to get this 'down into the weeds of minutia', but as I parse the question, it is also asking this... let's say a group starts a long rest at sundown, the LR is interrupted at midnight the same night. Does the group now have to wait until sundown the next evening to 'restart' LR, or once the interruption is finished after midnight, can the LR be restarted immediately? So, if it has to wait until day 2 sundown, then the benefits aren't available until day three sundown, or if the LR can restart early in the morning of day 2, then they would \$\endgroup\$
    – CGCampbell
    Commented Sep 26, 2022 at 11:34
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    \$\begingroup\$ @CGCampbell: The rules don't talk about calendar days, they talk about per 24 hours. As written, this would simply mean a rolling 24 hour basis. Arguably, this would mean you have to finish your rest at the same time or later each day (can't end at 0800 one day and 0759 the next), but most DMs I know of typically play it with a little flexibility there (I'd personally allow you to gain the benefits so long as long rest N+1 ends over 24 hours after long rest N began, which might be a little generous, but it still ensuring at least 16 hours between long rest benefits). \$\endgroup\$ Commented Sep 26, 2022 at 12:26
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    \$\begingroup\$ @CGCampbell: You didn't derive the benefits, so nope, no cost except the wasted time prior to the interruption. \$\endgroup\$ Commented Sep 26, 2022 at 15:40
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No

A character can't benefit from more than one long rest in a 24-hour period

They can take up to 3.

However, long rests are virtually impossible to interrupt (as opposed to being abandoned by the players):

If the rest is interrupted by a period of strenuous activity - at least 1 hour of …

It takes something massive to interrupt a long rest: dealing with an earthquake, a volcanic eruption, the ship the PCs are on sinking etc. combat encounters don’t interrupt a long rest because they last less than a minute typically.

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    \$\begingroup\$ @user28536 Examples after hypen are pretty normal as far as I know. \$\endgroup\$
    – Mołot
    Commented Sep 25, 2022 at 23:24
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    \$\begingroup\$ @user28536 the rules can be read this way. There is no solid consensus in the community, so your particular table should decide, how do you threat long rests. It's reasonable to assume that the answer depends on the game genre. \$\endgroup\$
    – enkryptor
    Commented Sep 26, 2022 at 10:27
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    \$\begingroup\$ Under your interpretation, you can't have long rest while inside a besieged castle... \$\endgroup\$
    – Trish
    Commented Sep 27, 2022 at 10:05
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    \$\begingroup\$ @Trish: That's not an unreasonable interpretation if the siege is of the active sort (not merely surrounding the castle and starving them out, but launching regular sorties). Historically, a fortification under constant attack would rotate out defenders so the defenders could rest; if there weren't enough to fully man the battlements while maintaining that rotating system, yep, people would go without sleep and become less and less functional over time. If anything that argues for enkryptor's interpretation; if the enemy can throw waves at you every few hours, you can't long rest. \$\endgroup\$ Commented Sep 27, 2022 at 19:59

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