Issue Summary

After modifying a workflow to add an approval step in a Jira Cloud business project, existing work items in the affected status can bypass the approval requirement. 

Steps to Reproduce

Initial Workflow Simplification

1. Remove all transitions, approvals, and statuses except "To do", "In progress", and "Done".
2. Save the workflow.
3. Ensure there are work items (dummy issues) in each status.

Workflow Modification

1. Edit the workflow again.
2. Add a new status called "Pending".
3. Create transitions between all statuses.
4. Add an approval requirement to the transition from "Pending" to "Done".
5. Save the workflow.

Test Approval Behavior

1. Attempt to move work items that were already in the "Pending" status to "Done".
   • Observed: The approval transition is not triggered; items move freely to "Done".
2. Move a work item from "In Progress" to "Pending", then from "Pending" to "Done".
   • Observed: Approval is required as expected.

Attempt to Reproduce

1. Remove all modifications, revert to default statuses, and repeat the above steps.
   • Observed: The issue does not occur again; approval is enforced as expected.

Expected Results

• Approval should be required for all transitions from "Pending" to "Done", regardless of whether the work item was in "Pending" before the approval step was added.

Actual Results

• Existing work items in "Pending" can bypass the approval and move directly to "Done".
• Newly transitioned work items (e.g., from "In Progress" to "Pending" to "Done") correctly require approval.

Additional Information

• No workaround is currently known; reverting and reapplying the workflow seems to resolve the issue for subsequent attempts.

Workaround

• Re-transitioning those issues to the status they are in and it should trigger the approvals workflow. There's a nice summary of how you can do this with bulk issue transitions or moves in this community query.