Originally Posted by
CollegeFlyer
And as long as all segments clear before check-in, you only get charged for the distance from your origin to your final destination. But if your segments clear at the gate, then you will get charged for the distance of each separate segment when it clears.
This is the key piece of the puzzle as to why the OP was charged the extra 500 milers. I was confirmed in F in advance on EWR-ORD-SAN using 5 500 milers. EWR-ORD was delayed and I got re-booked ORD-SAN on the next flight that same day. I was charged 2 500s for EWR-ORD and 4 for ORD-SAN. When I called M+ the agent explained that it was because the entire itinerary had not cleared ahead of time which technically is a correct statement as to how 500 milers work, and as to what happened with my itin. I didn't get the one 500 miler back