Has anyone been able to add in a workflow validator between statuses to only fire if a checkbox is null?
Yes, this is built in, no app needed. On a company-managed workflow, open the workflow, click the transition between the two statuses, and under Validators add a Field Required Validator pointing at your checkbox field. It blocks the transition whenever that field is empty, and for a multi-select checkbox "empty" means no option ticked, so that's your null case.
The thing that catches people out is the field has to be on the transition screen, otherwise the user can't set it and the transition just always fails. So add a screen to that transition with the checkbox on it.
If it turns out to be a team-managed project, there's no field-required validator there, so you'd lean on Restrict transition or the Remind people to update fields rule, though the reminder only nudges rather than enforces.
Best, Gabriela
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