I've been lurking for a while now, but finally have a question I can't seem to find a good answer for and I know you folks can help. So, this is my first post, please be kind

I am returning home this friday (4/24) from CID to RIC via ORD (UA7165 and then UA174). Both flights are upgradeable and I have 2 e500s I need to use.

Here is where it gets confusing (to me). As I understand the what I have read here and on the wiki, if I upgrade the whole itinerary (196 miles + 642 miles), it should take the 2 certificates because the total is under 1000 miles (838 to be exact). However, when I try to do so on .bomb, it says that I need 3 (as if I was doing each segment independently).

So I called the 2P desk and they said it should only take 2 e500s. Great! I had them put the request in. I guess I should be happy, but I am not the most trusting of folks and I half expect that if the upgrades clear, I will be asked for 3 e500s.

Am I correct to be paranoid, or should I just chill?

Thanks for helping a newbie.