> Those would never be taxable, as you paid for the miles Good point. > If I flew for work for a decade and accrued a bunch of miles and redeemed them only la

> Those would never be taxable, as you paid for the miles Good point. > If I flew for work for a decade and accrued a bunch of miles and redeemed them only later, in what year would they be taxable? The year you redeem them I would think. Just like you don't recognize typically recognize investment gains until you actually sell and receive those gains. It'd be nonsensical to tax me on fake airline bucks for an airline that might be out of business later this year, or might devalue their points. The (as I would see it) taxable benefit occurs when I successfully redeem those fake airline bucks for a real, valuable service. > If I mixed personal and business travel in earning miles, what portions would be taxable and when? Seems like you'd need to maintain separate accounts, so when you redeem them you say, "yeah I'm using 20k points from my personal account and 30k from my employer-paid perk account, knowing I'll be taxed on the current value of the 30k taxable points". Overall it does seem like a PITA, it's just funny to me because "this is too much of a pain to deal with so let's ignore it" doesn't seem like something the IRS usually says. I suppose overall the issue must be (as another commenter put it) "small potatoes" to the IRS.