Buying first-class vouchers?

Is it possible to buy an upgrade voucher for a given airline and apply it to any ticket that you buy? Someone mentioned that these are available on the gray market, but it sounds shady to me. Are these vouchers same-as-cash? Seems like they’d be tied to a given passenger, but maybe I’m just assuming airlines will be their usual panicky selves…

The ones I have here in my hand (for Air Canada) specifically state that only you or someone traveling with you can benefit from them. They have serial numbers, which are entered at check in time. They can be used on other Star Alliance airlines, and I would presume it’s safe to assume that most airlines use similar systems.

How did you get ahold of those vouchers?

I’ve been issued vouchers by my frequent flyer program (Star Alliance, Lufthansa) for flying X number of miles in one year (in my case 100k).

eBay is loaded with offers.

What’s the grey market?

I have not seen it defined but my understanding of “grey market” is where the sale is not illegal but the manufacturers or original suppliers don’t want the item sold in this way. An example would be where a supermarket chain are buying expensive perfume abroad and selling it in their shops. The manufacturer may want to keep its exclusive image by only selling through up-market outlets.

In this case the sale may or may not be illegal - vouchers like these are quite likely to say “Not for Resale”.

Is this what other people understand by the term?

So then, can anyone tell me the likelihood of an airline honoring these vouchers if procured via eBay?

You might want to contact the airline in question. However, I doubt you’ll get an honest answer. If you personally know a travel agent or someone in the airline industry you stand a better chance of finding out whether such vouchers are accepted or not. It’s more of a crapshoot than anything else.

For me, it’s a no brainer. They are not worth it. You run the risk of not making a flight (going or coming) and if the trip is that important but saving a few bucks on a gray market voucher is more important, I don’t understand the potential savings. Sure, it’s only an upgrade voucher but whose to say the airline won’t screw with you at checkin or even at the gate, even though all available information up to that point said you would be fine?