Checklist Milestones will be skipped if an Exiting Milestone is overlapping with an Entering Milestone. With milestones, the checklist will convert the furthest option available when assigning new statuses for Candidates. To prevent an Exiting Milestone is be overlapped, The Entering Milestone will need to be modified.

To modify the Checklist:
  1. Navigate to onBoard
  2. Settings > Checklists
  3. Edit into the checklist in question
  4. Click Edit across from the Entering Milestone that follows the Exiting Milestone
  5. Change the Status Changes to "No Change" or "Exiting Milestone". (Note: If changing to Exiting Milestone, verify that the next step doesn't also include an Entering Milestone. This will cause the same overlap as previous)
  6. Change the Candidate Status if required to reflect continued status progression
  7. Click Save