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I'm looking to transition when a Sales Order is fulfilled and goes from pending fulfillment to pending billing, I tried a transition on after submit status = pending billing but that did not work.  Any one do this before I spend hours trying different things?

You need a script on the transaction that triggers the status transition to trigger your workflow

or a scheduled workflow that looks at status and then checks a box and does whatever it needs to do on a 30 minute - day delay or whatever you deem appropriate

ok, thank you, I would have tried many things before releasing that.