Well it is clear to must that United upgrade system is broken. Matthew posted about this a week or so ago. I’m also like Matthew and this UA knows they have problems and the fix it to make it harder to passengers to see “R” space on UA flights. “R” is the booking class that represents upgrade space from Economy to the next cabin level. If there is R space at time of booking and you try to upgrade it should clear right away, from what I can tell this works. BUT if there is no R space open when you request an upgrade you will be placed on a wait-list. The way it should work is, when R space opens up and you are on a wait list the upgrades should clear based on your booking class and status with UA. However it is clear that when R space opens up, the system is not clearing people on the wait-list and will let new request trump people waiting on the list. Here is a good example a friend is flying from IAD to MUC on Friday, here was wait-listed at time of booking. You can see “upgrade requested”
Today when checking "R" space for him because of the known issues I found that there was spaces open. One way to check for upgrade space it act like you are making a new booking on United.com and click "advanced search then after entering the date and route you are checking, click the box next to “MileagePlus Upgrade Award”, then search. You will see if the flight has “R” space like shown here.
It clearly shows if I wanted to book and upgrade I would get the open R space but clearly my friend is on the wait-list. So I quickly called United and get a lady who just kept saying you are still wait listed. I told here I see “R” space online, click put on hold.. I was on hold for about 5 min and said “you are now upgraded” I asked, why did it not clear automatically? She said, “Sir if I knew why the system did half the things it did I would be in management”. I chuckled and thanked her.
So the only way to make sure you get your upgrade when waitlisted is to check online all the time. What a pain, I know! When you see R space call right away and tell the agent you see "R" space and ask them to clear the upgrade. The thing is when they do this if you are not at the top of the wait list you will just take the R space and if anyone else was ahead of you on the list, you just took their space. So it is a game for sure, if you know how to play this UNITED upgrade game you could be a big winner. Good Luck!