Force comments when changing a status

When using boards for re-ocurring items, I need a way to force a commentary update from the person changing the status.
This needs to be differtn each time so cannot be a static ‘update’ which the system auto creates - needs to be a free text update. It’s needs to be strict enough that the status will not change without a commentary being added.

I dont mind where this commentary goes (i.e. another text column or into the updates page (speech bubble area)), but it must be a mandatory requirement.