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I am doing a pretty huge edit right now.
For some reason, whenever I have an In Point (I) and Out Point (O) selected on the timeline, indicating that I want to play just that segment, PPro starts back at the starting point of the sequence instead of looping the IO segment.
Any ideas on how to fix this?
Check Preferences > Timeline.
If Premiere is acting weird
FAQ: How to reset (trash) preferences.