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Try this, Before modified record saved condition pre(owner)<>owner
Action: update boolean field='Y'
You need to work out where the issue is, add a task to your workflow, if the task works, the action is the issue, if the task doesn't work then your workflow formula is the issue.
The workflow should be on the trigger "Before Modified Record Saved".
The condition should be [<Owner>]<>Pre('<Owner>')
Action should be Update Field and select the boolean field.
Let me know if this helps.