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I have a group of SLA Processes that are working, they are using a custom date field as a base for the Milestone timeline; however, I need that under a special set of circumstances, a change in the custom date can trigger a change on the Timeline; but I can't apply a trigger directly on the Milestone to achieve that and I can't seem to be able to reset the SLA Process and make it execute again.

Any suggestions?

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I suspect you'll find the key to the solution to your problem in the following link: https://success.salesforce.com/ideaView?id=08730000000JTEg. If one wants to update the SLA minutes on a milestone, the process first has to be removed from Entitlement records. Salesforce is considering adding versioning to the Entitlement Process which would avoid this issue. As a workaround, you can copy a process to make changes and then associate the new process to any entitlements.

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