When did it not reroll? Halfling luck only works on attack rolls, ability checks and saving throws. So not damage dice for instance.
I noticed this on one of my player's sheets. I unticked and then re-ticked the box and it seemed to start working again.
Dear Patrick, I know it only works on attack rolls, ability check and saving throws.
The issue is, when you hover the mouse over the roll you can see if it has rerolled a 1 - my players did an athletic check and rolled 1 and it said "1d20" rolled nothing else.
I re-ticked the box and everyting but nothing worked and that's why I posted this to see if others had problems. :)
I have figured it out - It's a Charactermancer glitch.
All characters created with Charactermance automatically has the box checked but the sheet does not regocnize this.
Solution: Uncheck the box then re-check it and all your saving throws, ability checks and attack rolls should start with: "1d20<ro1 + ..."
This appears to be a common issue with this sheet: requiring manual activation over programmatic. this should be reported to the D&D 5th Edition by Roll20 thread.
For the record, insight is a skill check, not an ability check. Halfling luck doesn’t work on skill checks.