I'm sure this has been hashed out many times but I was unable to find an answer in my quick search. To settle a discussion with a co worker, here's the scenario: Single pilot operating under 135.265 with over 10 hours rest prior to starting the trip. The route is two legs, scheduled for 7.5 hours of flight time. The first leg is scheduled for 5.0 hours but encounters heinous headwinds and takes 6.0 hours. The next leg is scheduled for 2.5 hours. Can the pilot depart on the second leg knowing they will exceed 8 hours flight time?