Have a situation where my return flight from Australia is going to be changed due to a medical condition, and the insurance company is going to up for paid C.

Have already applied for a SWU to C on the current itinerary, via a sponsored instrument, but that will be changing (hopefully) to fly me home earlier, as soon as I'm medically cleared. The "Magic 21" upgrade window opens tomorrow on the original itinerary, and I'm guessing just to make this all more complicated, it will probably clear.

Because I will only believe the insurance company when I see it, I'm hesitant to remove the SWU from my current return, as if I have to reschedule or upgrade myself, don't want the sponsor to have to go through any further paperwork or rush to re-sign another bluey. I presume that, if all goes well through the insurer on rescheduling into paid C, the SWU will simply re-deposit back into his account? Of course, would follow up with him to be sure it really does appear, as we all know the stories where they go missing into the .bomb world.

Not to mention I might consider still using the SWU to put myself in F instead.

Anything else I should do? Another strategy I should consider instead?

Yes, in about a week. In your case, the original return will be canceled, whether you cancel it, or fail to use it. Unused and unexpired upgrades go back to the owner.

Even if this was your own SWU, you would not be likely to use it in this situation. As this is not your SWU, unless your sponsor has another SWU, you'll be riding in C.

Really? I thought the insurer was going to use my original PNR and upgrade the return one way to paid C, as that's a less-expensive alternative than purchasing a new one way C. If that's the case, wouldn't the SWU follow the booking?

I don't know how that is going to work. I'd think if there is any credit left on your return ticket, the return is going to be canceled and the credit, less change fee, used to purchase a one way in C.

If there is a way for a 3rd party to the take the 2nd party's ticket, and refare it to the next class of service with the 1st party, I'd like to know.

You can't upgrade something unless there is inventory, and since your SWU hasn't cleared there is no upgrade inventory. Your insurer might be telling you they can buy an upgrade for you now, but I've never heard of such a thing. If there is, I'd like to have the website or phone number that lets me do it.

But let's say I'm wrong and there is a way to buy this upgrade now and the SWU does not get automatically sent back to M+ for processing to be redeposited to your sponsor's account. That leaves one problem: UA does not allow double upgrades. Yes in this forum you'll read about the odd person who has pulled off the impossible, but as a matter of policy it isn't done.

Sorry if I mis-typed. I didn't mean to infer they are going to purchase me an "upgrade", but that my ticket would be upgraded (refared) to a C on the return, thus retaining the initial value toward the return portion. Not positive that's what they're doing, or if they can, but it's my suspicion, as they wouldn't be able to access the residual fare amount any other way, and that would be a very financially poor way of handling the situation.

Since I would then be on a paid C fare, the SWU wouldn't be a double upgrade. It would simply be upgrading the C fare.

Hope that makes more sense. I wasn't clear enough earlier.

WOW - what insurance company would spring for a C fare on SYD USA???? I want to get their insurance .

In any case, I hope you are feeling ok and enjoyed your time in SYD.

Upgrade != Re-fare.

Re-fare means new ticket. Means the SWU is lost, and sent back to M+ for re-processing to the owner's account.

As for financially poor, give the timing this will likely book into full fare business class, and it won't be cheap. If you can get another SWU, your odds of upgrading to F are extremely high; at worst it just means one less airline employee in F.

Actually, most US policies with "evacuation" coverage will if it's medically necessary. Since I suffered bilateral PEs (blood clots in both lungs) for the flight down, the docs want to ensure I can have my legs elevated and enough room to move around for the flight home. Since the docs put it on the form as medically necessary, the insurer pays for it. I actually offered to use the SWU if they could find NC space, as I don't believe in making the insurance company pay if not necessary, but we know how that is

It appears they are going to make the changes on the same PNR. I'll see what happens with the SWU after it's re-issued.

I am doing much better, and Sydney is a lovely city! Just wish my lungs had allowed me to explore more of it on foot, but the bus/ferry system has been great.