Given your setup, the path should start at 8:00 AM, get to the middle stop a short while later and then depart at 9:00 AM and end the path at the third stop around 9:03 AM.
So can you double check that the ending time on the third stop is 9:03 and not 8:03
Also, can you bring up the properties of the middle stop and check that the time windows start and end are set to 9:00 AM and 10:00 AM?
Jay Sandhu