StopJetLag analyses and responds to all of these factors before formulating its Plan for you. Don't settle for anything less.
When your answer is yes, this indicates that you will not be able to sleep on your upcoming destination time during your flight.
When your answer is yes and you are going east, this also indicates that you will not be able to get enough sleep on your destination time during your flight.
Generally speaking a connection that entails changing planes will force you to stay awake and therefore it is not a possible time to sleep on either departure or destination time during the time between connections. Possible sleep times are therefore evaluated for other sections of your trip.
For most trips (especially afternoon and evening flights) the answer to this question is that it is not possible (and/or desirable) to change to destination time before departure. Your StopJetLag Plan does allow this choice to be made.