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Is there a way to track who changed a permission set assignment on a user, and when — there doesn't seem to be an obvious History Log setting or event trigger point for this.

Answer

Activate History Log logging on the FND_USER_ROLE_TAB table — it may not be visible/enabled by default, so make sure the option to show the Foundation1 component is turned on wherever you're configuring History Log so this table shows up as a selectable option. Once logging is active on it, every modification to a user's permission-set/role assignments gets tracked the same way History Log tracks changes on any other logged table.

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