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The question's been asked before elsewhere, but for lack of an authoritative answer:

If a character has a sufficiently small constitution score, it's conceivable that, when they use a hit die to heal during a short rest, that the roll might not be enough to offset the penalty.

The PHB doesn't have a lot to say on the matter (page 186):

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.

For example, given a character with constitution 4 (a modifier of -3) who rolls a 1 on their hit die, so the total is -2.

I could think of a few ways to handle this situation, and arguments for each:

  • have the character lose two hit points, that's what the numbers say
  • have the character neither gain nor lose a hit point, the rules only mention "regaining hit points" with a hit die, not losing.
  • have the character gain a hit point, they did spend an entire hit die
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You regain zero hit points.

Jeremy Crawford said on Twitter:

You regain no hit points if you spend a Hit Die and your Constitution modifier reduces the total to 0 or lower.

This ruling was made official in the 2017 Errata to the PHB:

Short Rest (p. 186). After applying your Constitution modifier to a Hit Die roll, you regain a minimum of 0 hit points (6th printing).

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It appears that there is no minimum result for a die roll.

However, in this case, you are rolling for the number of hit points that the character will regain. I think with this wording that any result lower than 0 would be treated as a 0. You can't regain a negative number.

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    \$\begingroup\$ Well, assuming you’ve lost HP before, you could “regain” an old wound... \$\endgroup\$ – MrHiTech Feb 17 '19 at 6:52
  • \$\begingroup\$ It looks like a parenthetical note was added to set a minimum of 0 HP regained as of the 2017 PHB errata: media.wizards.com/2017/dnd/downloads/PH-Errata.pdf \$\endgroup\$ – V2Blast Feb 18 '19 at 22:48
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According to D&D Beyond, PHB, Chapter 8 (Adventuring), Resting section, Short Resting subsection:

....For each Hit Dice 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).

I don't know if the printed PHB does not state this, but that is the listed minimum I found.

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    \$\begingroup\$ The printed PHB is missing the parenthetical "(minimum of 0)" \$\endgroup\$ – rampion Feb 18 '19 at 22:07
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    \$\begingroup\$ @rampion: It was changed as of the 2017 PHB errata, and the Basic Rules were updated in 2018 to match. \$\endgroup\$ – V2Blast Feb 18 '19 at 22:44

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