Salesforce Service Cloud Milestones Not Re-Evaluated When Case Ownership Changes

In Salesforce Service Cloud, Milestones that are part of an Entitlement Process are not automatically re-evaluated when a Case owner is changed through the standard UI. This is working as designed because Case transfer does not invoke Entitlement recalculation. The following sections explain the known scenarios and how to address this limitation.

Known Scenarios Where Milestones Are Not Re-Evaluated

The following actions do not trigger Entitlement Milestone re-evaluation:

• Changing the Case owner through the UI (clicking Change next to the record owner's name)
• Field updates performed as a Milestone action or a Workflow action

Example scenario: A Case owner is changed through the UI, which also triggers a Process Builder that runs a Flow. The Flow updates a field used in the Milestone criteria (e.g., "Value1" = Milestone1, "Value2" = Milestone2). Even though the criteria field is updated, the Milestone is not re-evaluated. However, if a checkbox field that performs the same action is used instead of changing the owner, both the criteria field and the Milestone are updated correctly.
Similarly, creating an Apex trigger on Case to update the checkbox produces the same issue: owner changes trigger the Apex, which updates the checkbox, which runs the Flow — but the Milestone is still not updated because the root trigger is a Case transfer.

Available Workarounds

• Edit and save the Case: After changing the Case owner, manually edit and save the Case. This triggers Milestone re-evaluation and removes the Milestone if the criteria is no longer met.
• Use an Apex @future method: Create an Apex @future method that performs a Case update after ownership transfer. The Milestone will be re-evaluated when the @future update runs.
• Use a different Milestone criteria: Redesign the Milestone criteria to avoid conditions that depend on Case ownership if real-time re-evaluation is critical.