I am trying to prevent a work item from transitioning to a waiting for approval status unless a 8 or more attachments are attached, I am also trying to apply this rule to 2 status transitions. I have a team that requires a number of forms completed before they can start working on a task.
I have tried using the workflow rule 'Restrict to when a field is a specific value.'
For this field Attachment
Review its value as A number and Check if it Is less than
This value 8
Even though I meet the requirement I have set, of 8 or more attachments the transition to 'waiting for approval' does not become available. I have tried attaching the attachments prior to ticket submission and after ticket submission and I run into the issue in both scenarios. I do also have a Jira form attached, so I'm unsure if that would affect anything.

