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I have a field on the Case object which when updated to true needs to trigger the assignment rule. It seems that an inline edit does not trigger the rules so I think of writing a custom detail page button which updates a field in my case, and I need the case assignment rules to be evaluated as a result of this record update. What is the best way to achieve that?

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You need a trigger for this. See here for a sample on how to do this.

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