Upgrade on international award ticket
 

I'm 1K (and a Million Mile Flyer) but United tells me that if i book an international flight with miles, I can't be upgraded either complementary or with Plus Points. I also tried doing it on the website but was blocked there too. Apparently if it was domestic, I could be upgraded if i paid the taxes and fees with a Chase card. Not sure what's more ridiculous - that paying the tiny amount with a Chase card changes the result or that its only for domestic. Does anybody know a way around this?

Welcome to FT!, lfinger

correct
correct, you can waitlist at least, no guarantee of upgrades
Become a GS, they can -- but just GS mileage tickets

You may be offered a cash upgrade opportunity and you can waitlist for IN mileage award.

lfinger, welcome to FT; stick around!!

UA does not offer complimentary upgrades (CPU) on the long-haul flights you're talking about. The fact that you're using an award ticket neither helps nor hurts you as far as that goes.

For CPU-eligible flights, I don't think you actually have to pay the taxes with a Chase card; I think it's enough just to be a cardholder. But you still have to have Premier status to get upgraded; the card merely lets you receive those CPUs, based on your status, on award tickets also.

GS can buy awards and upgrade with PP - but both the miles and PP must come from a GS account - every now and then you hear than some agent use GS PP to upgrade an award from a non GS account but it is very rare and probably a mistake.
I do this when my wife flies with me - Company pays for my ticket, i buy her a saver award in economy with my miles and upgrade her with PP - IMO - One of the best perks for GS.

Minor nuance - certain international flights are eligible for CPUs but they are short-hauls (Canada, Mexico, etc).
And some domestics are ineligible (east coast to/from HNL, ps, etc).

It USED to be the best perk of GS when you could call and upgrade an entire itinerary but now that its one segment, one direction, its honestly not much value to me. When my spouse and I travel together internationally, we want to have seat assignments together in the same cabin. No way I'm playing upgrade roulette on a long intl trip. So instead of paying the currently exorbitant J prices on UA and gambling on an upgrade clearing one-segment for her, I'm paying cash for two J seats on other airlines instead, getting what I want (including better service) and paying less money.

I was just looking at reservations for January to San Juan PR. The flights within the Continental US are displaying "Complimentary Premier Upgrade Requested" but the flights to/from SJU are not. It looks like UA may be becoming more restrictive as to which flights will be CPU eligible.

Don't mistake UA IT failures for policy changes. There are more of the former than the latter.

I have cpu requested showing on a -SJU flight.