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I am working with Milestones, and have setup a field update that checks a box on the case. I then went to Process builder and had the milestone close when that box is checked. If you manually check the box, it closes the appropriate milestone, but will not if I let the process run from

Milestone Workflow > Checkbox > Process builder.

Attached are screenshots of my configuration. Any help would be great!

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I assume that what you're saying is that the field update for when a Milestone is completed updates a field on Case, and then is not triggering the Case Process Builder to fire. If that's correct, then that is unfortunately expected. It's a known issue with no fix. Apex Triggers, however, will run on these field updates, so if you feel comfortable with it, then that's an option.

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  • The KI refers to WFR, not PB but SFDC is known to be somewhat loosey-goosey in terminology re: "workflow" - I don't doubt your answer; be interesting to see if an after save flow would execute
    – cropredy
    Commented May 14, 2021 at 22:09
  • @cropredy Yeah even though it only explicitly calls out Workflows, it's the same for Process Builders. I faced this issue myself. I didn't try an after save flow though.
    – Nicholas Savini
    Commented May 14, 2021 at 22:13
  • Thanks. I was afraid that this was the case @NicholasSavini. It's such a smooth process but was hoping that it would work that way. I am not familiar enough with Apex enough, so I was hoping that this would work out! What would an after-flow save look like? My mind goes there in terms of feeling as if the record is not invoked to be saved. I thought perhaps another change (status or something similar) would cause the record to save and milestone to close. I use this process by marking a date resolution time, & it will close it from within the case. But when setup from entitlements,it doesnt
    – Gabe Sanchez
    Commented May 19, 2021 at 8:54

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