Unlike a long rest, after which a character automatically regains all lost hit points, a short rest is reliant on characters choosing to roll hit dice and regain hit points based on the rolls. When taking a short rest, it is up to the player to roll hit dice until they're satisfied. D&D Beyond allows you to check these rolled dice off (to keep track of how many you have left), but you must manually heal the amount that you would otherwise heal from spending hit dice during the rest.
In addition to Halfwing’s comment, a note for anyone who uses or plans to use the the checkboxes to track how many hit dice have been spent.
When it comes to short rests and spending Hit Dice, RAW is that a player rolls a single Hit Die, adds their Con mod to the roll and regains that total number of HP. At which point the player can choose to spend another hit die, repeating the process until the player is satisfied with the number of HP their character has regained, or the character runs out of hit dice. The advantage to this method is that a player cannot accidentally “waste” either the hit dice or the opportunity. By choosing to spend dice on an individual basis the player can can make the decision to either spend or reserve the resource on an individual basis.
However, when we hit the Short Rest button, the character sheet requires us to declare the number of Hit Dice are spent all at once and cannot be changed without taking another short rest.
What I suggest to my players is that they individually spend the desired number of hit dice first. Afterwords they can hit [Short Rest] so they already know the total number spent that rest before having to check the boxes to track them.
Just wondering if I'm doing anything wrong, are we supposed to go roll manually?
Unlike a long rest, after which a character automatically regains all lost hit points, a short rest is reliant on characters choosing to roll hit dice and regain hit points based on the rolls. When taking a short rest, it is up to the player to roll hit dice until they're satisfied. D&D Beyond allows you to check these rolled dice off (to keep track of how many you have left), but you must manually heal the amount that you would otherwise heal from spending hit dice during the rest.
In addition to Halfwing’s comment, a note for anyone who uses or plans to use the the checkboxes to track how many hit dice have been spent.
When it comes to short rests and spending Hit Dice, RAW is that a player rolls a single Hit Die, adds their Con mod to the roll and regains that total number of HP. At which point the player can choose to spend another hit die, repeating the process until the player is satisfied with the number of HP their character has regained, or the character runs out of hit dice. The advantage to this method is that a player cannot accidentally “waste” either the hit dice or the opportunity. By choosing to spend dice on an individual basis the player can can make the decision to either spend or reserve the resource on an individual basis.
However, when we hit the Short Rest button, the character sheet requires us to declare the number of Hit Dice are spent all at once and cannot be changed without taking another short rest.
What I suggest to my players is that they individually spend the desired number of hit dice first. Afterwords they can hit [Short Rest] so they already know the total number spent that rest before having to check the boxes to track them.
Creating Epic Boons on DDB
DDB Buyers' Guide
Hardcovers, DDB & You
Content Troubleshooting