So I guess I am in the same situation. As a gold member, used miles from my account to upgrade on a DCA-IAH-SJU flight this Thursday 07 MAY. The IAH-SJU flight #1753 cleared right away, but I was placed on the "waitlist" for the DCA-IAH segment (flight #259). I know its a highly trafficked elite route and have watched as First class fills up.

As I understand it, those getting upgraded (excluding people buying B-up fares / first class tickets) should only be Plat's on mileage upgrades or Gold/Silvers on mileage upgrades waitlisted before me and not EUA's, correct?

The DCA-IAH flight departs at 12:20pm Thursday so at 12:21pm Wednesday EUA's kick in and my mileage upgrade is no longer a priority until at the airport and the standby list is used, is that also correct?

Seeing as the San Juan flight is relatively still wide open, I could assume a EUA for that segment would have cleared and I wouldn't have had to use the 15k miles, especially when there is a good chance it wont clear on the DCA-IAH leg. (The only reason I used miles was to ensure the upgrade a month ago in order to sit with my friend on a reward ticket since we are all going to San Juan for his bachelor party- I'm a groomsman)

Anyway, my question is if the mileage upgrade doesn't buy you anything in the 24hr & 3hr mark, what's the point of using miles if I will just be put behind the EUA's- Platinums and Golds on higher fares as I'm on a L fare, if I could stand to get my own EUA on the IAH-SJU flight. Basically why burn 15k if I could have gotten the IAH-SJU portion for free, besides peace of mind of course and is there any sense to just canceling the Series 0 upgrade and letting the EUA's run their course? And is there a fee for Gold's to do that- sadly I'll be back to Plat after this flight...

Thanks for your thoughts!