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I can only tell you how it works from SFDC, which might help (or not!).
Sync to SFDC: Auto Assignment only assigns the first time the lead syncs. SFDC needs a special trigger or a Change Owner to re-assign the lead to someone else.
Usually I sync all leads to Queues, where they wait until MQL and then get reassigned. I do this (usually) by setting Lead Status or Lifecycle Stage=MQL which triggers SFDC to run the assignment rules again.
This flow action does not have an error unless the lead is missing required creation data.
Is there a way to have MSD do something similar? Could you use Change Owner with Choice Steps?
Josh, what flow action do you use to Change Owner? That's what I was hoping to do - similar to what we do today within the "Sync Lead to Microsoft" flow step (where we have a series of choice steps based on country value) - but there is no such flow action available.
I guess MSD doesn't have a Change Owner action then. With SFDC integration, it is called Change Owner.
Maybe check with Support?