Originally Posted by Poco
While you do book individual segments, they show up (in my flight wallet at least) grouped together into trips. I then need to select which trip I want which then pulls up the segments that make up that trip. I make my original bookings through my corporate travel agent, so that may affect how the flights get organized in the wallet. I've never had trouble upgrading the first segment, it's the return (or second) segment that causes problems. I haven't tried a trip that has more than two segments yet.
Interesting. The city pass I used (granted, it finished last summer and things might have changed, and I had no TA involved) just let me pick individual segments. Did not arrange them into "trips."