How much is the difference in cost between the cheapest economy and the upgradeable fare, typically?

So this has nothing to do with the TSP, but whether it's ethical to buy a more expensive, upgradeable ticket.

I'm sure no one's done that before, right?

This is slightly worse than usual, because there is a specific financial incentive to take the bucketshop fare, which he is undermining by booking a (semi-)flexible ticket.

Assuming that he is authorized to travel on paid J, anything that doesn't cost the company more than that should be fine.

An example: J ticket is $6000, the cheapest Y is $1500, and upgradable Y is $3000. Options include:
1) Buy J at $6000 - allowed by company policy, director arrives at destination more rested and ready to be productive than he would in Y. No ethical question.
2) Buy $3000 ticket, upgrade with SWU, take $1500 TSP payment = $4500, company saves $1500, director arrives at destination more rested and ready to be productive than he would in Y. I see no problem with this, but this seems to be where the difference of opinion here lies.
3) Buy $1500 ticket, sit in the back, take $1500 TSP payment = $3000, company saves $3000, director arrives at destination more travel weary than he would have in J. No ethical question.

I guess you could argue that, but I'd say it's a moot distinction because both have a financial incentive to book the economy fare. That's why the program exists.

I so no ethical shaky ground. I am assuming the OP has a travel policy that entitles him to fly first/bus on flights over a certain distance, but if he is willing to forgo that entitled seat for one in coach, he gets a bonus. If he books a coach ticket and upgrades with his own points, I think it is fine.
He is on the same moral ground as I am.

I fly only domestically, and am never allowed to book anything other than coach, if I book a higher fare to get myself on the upgrade list, then we have an ethical breach.

There is no issue with me using miles or being automatically upgraded (depending on if I am flying AA or CO).

I think the OP is ethically correct as long as he buys the cheapest applicable coach seat.

Typically, unrestricted Y is much more expensive than the cheapest biz class fare. Depending on the route, there can be a several hundred dollar difference between the cheapest coach fare and an upgradeable coach fare. If the OP books an upgradeable fare but only seeks reimbursement for the lowest available fare at the time he/she booked, then there is no ethical issue (in my view). However, if he/she seeks reimbursement for the more expensive coach fare simply to get the chance to upgrade, that would be an ethical violation and likely would violate the company's travel and/or business conduct policy.

Here's another wrinkle: the flier takes the $1500 payment, and is prepared to fly economy. On the day of departure, upon checking in at the airport, a sign at the counter is offering one-way cash upgrades for $500.

If he/she purchases the upgrade (ostensibly using the funds from the payment), is any "violation of ethics" mitigated?

I think it is okay as one is paying the upgrade with personal funds. The total cost to the company is only for Y class.

I used to work for a company that gave you back a portion of the savings if you stayed with friends instead of in a hotel, etc. I always thought that was a good idea.

Mike

It seems to me that as long as the Y ticket plus $1500 is still less than the business class ticket you are entitled to, there is no harm no foul regardless of if you then use any instrument to upgrade. The company is still paying less than they would if you simply booked in business.

That's a different situation and most companies (that I know of, anyways) do this.

Mine does as well, but it is only $100 per occassion. I have a month long assignment and I can stay with relatives, however considering how little this I am not. I even tried to get the amount negotiated, but to no avail.

My company has well-defined rules on what booking classes we can use for travel, so there's no wiggle room. However, they do make allowances for employees who have to book refundable tickets because of the need for flexibility (and it's simply cheaper to have a refundable ticket than to deal with the change fees). I've also gotten upfront approval to purchase a higher fare class for the purposes of upgrading from my manager (and, his manager) when budgets were cut and we couldn't book business class any more.

Booking a more expensive ticket than necessary for personal reasons does seem to be shaky ground. I would err on the side of avoiding any appearance of impropriety and ask Finance to clarify the rules.

The payout stipend waives the employee's right to require the company pay for the C-class seat he is eligible for. The payout stipend is not for the employee's promise to sit in a big seat in front.

Therefore, no ethics problem.

Similarly, my company pays $40 per diem. Whether I actually spend $40
to eat, or pocket the $40 and eat TV dinners using my hotel room microwave, is irrelevant to the company. They know that each day I am travelling for them is $40 out of the company's funds. It's not important whose pocket that $40 ends up in....mine or some restaurant's.

I used to work for a company in Southern California. One Friday, they told me I had to be in Las Vegas on Monday for a huge week-long convention. All flights were sold out; they finally found a Y-class ticket for $677 round trip. The usual fare is $78.

I kept the Y-ticket and drove there myself (300 miles one way). The Saturday following the convention, I drove myself back.

Later I applied the full-fare ticket (as good as cash) to several personal trips.

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On another occasion, I needed to report to OKC on Monday for a job interview. A Y-ticket was sent to me. Again, I kept the Y-ticket, found a M-class ticket (requiring Sat overnight) to DFW. On Sat, I flew to DFW, hung around DFW eating delicious BBQ, and got in my self-paid rental car and drove to OKC Sunday night. I turned in my bargain National car, and picked up the Hertz car that was already waiting for me. Monday night, I turned in the Hertz car, got into another rental car and drove to DFW for my flight home. Even after the additional hotel, car rent, and BBQ charges, I came out ahead.