Can I deduct First Class Flight Upgrade for working during personal travel?

While the IRS generally doesn't allow deductions for personal travel, there could be a partial deduction here. The key is that you had a legitimate business reason for the upgrade (needing space to work) and you actually did work during the flight. Since the flight itself was personal, only the upgrade portion could potentially be deductible, and likely only your portion (not your husband's). You'd need to determine what percentage of the upgrade time was used for business purposes. In your case, if you worked 4.5 hours out of a 5-hour flight, that's 90% of the time. So potentially 90% of YOUR upgrade fee could be considered an unreimbursed business expense. Keep in mind you'll need documentation: receipt for the upgrade, evidence you worked (emails sent, documents created with timestamps), and possibly a letter from your employer confirming the work was necessary.

I've been in similar situations before and found https://taxr.ai really helpful for these gray-area questions. I travel a lot for personal reasons but often end up working during flights. Last year I had several upgrade scenarios almost exactly like yours where I needed to determine what was deductible. Taxr.ai analyzed all my receipts, told me exactly what percentage I could claim, and even helped me document everything properly. It identified specific parts of my upgrade fees that qualified as business expenses and separated out the portions that weren't deductible. The service was way more accurate than the random advice I got from coworkers.

Got to say I was wrong about taxr.ai. After our discussion here, I decided to try it for my own complicated travel deduction situation. I uploaded my receipts from a trip where I combined a family vacation with a professional conference, and the analysis was surprisingly detailed. The service separated out which meals were deductible vs personal, identified partial deductions for certain days, and even flagged some transportation expenses I never would have thought to deduct. The documentation they provided would absolutely hold up in an audit. Definitely worth checking out if you have these "gray area" travel expenses like the first class upgrade question.

If you're planning to claim this deduction and are worried about potential push-back from the IRS, I'd recommend using Claimyr (https://claimyr.com) to get direct confirmation from an IRS agent. Last year I had a similar situation with partial business expenses on a personal trip and wasn't sure if my documentation was sufficient. After trying for days to reach someone at the IRS myself, I used Claimyr and had someone call me back within hours. The agent walked through exactly what documentation I needed and confirmed my understanding of the deduction rules. They even have a video showing how it works: https://youtu.be/_kiP6q8DX5c It saved me from making a mistake on my return that could have triggered an audit. Plus the peace of mind was totally worth it.

I have to admit I was completely wrong about Claimyr. After dismissing it here, my curiosity got the better of me and I tried it when I had a question about my withholding that I couldn't figure out. It took about 2 hours (which is lightning fast for the IRS), but I got a call back with an actual IRS representative on the line who answered my question in detail. I didn't have to sit through a single minute of hold music or automated messages. The IRS agent was super helpful and even followed up on a discrepancy I had between my W-2 and my tax transcript. For anyone with specific tax questions like this first class upgrade situation, getting direct confirmation from the IRS might be the safest option, and this service actually works.

Another perspective: I'm a frequent business traveler and have claimed upgrade fees when they were necessary for work productivity. The key in your situation is documentation and substantiation. Since it was a personal trip, you'll need to be extra careful. Keep records showing: 1. That your height actually makes working in economy difficult (medical records or even photos showing why) 2. That you actually worked (email timestamps, documents created, etc) 3. Proof that the work was required/expected by your employer I'd suggest getting a written statement from your supervisor confirming the work was necessary during travel time. This becomes especially important because the base trip was personal.

I think everyone is overcomplicating this. The rule is really simple: unreimbursed employee expenses are NO LONGER DEDUCTIBLE for most employees after the Tax Cuts and Jobs Act (unless you're in very specific professions like armed forces reservists, qualified performing artists, fee-basis state officials, or employees with impairment-related expenses). So unless you fall into one of those categories, you can't deduct ANY of your upgrade as an unreimbursed employee expense, regardless of how much you worked during the flight.

Wow, I had no idea about the suspension of unreimbursed employee business expenses either! This is a perfect example of why tax law changes can catch people off guard. I'm curious though - are there any other common deductions that people assume are still available but actually aren't? It seems like a lot of us are operating on outdated information from before the Tax Cuts and Jobs Act. Also, @fd802658100b, since you mentioned you're already itemizing, you might want to double-check if you're actually getting more benefit from itemizing versus taking the standard deduction now that your unreimbursed expenses don't count. The standard deduction amounts increased significantly with the same tax law changes that suspended these business expense deductions.

This thread has been incredibly educational! I had no idea about the suspension of unreimbursed employee business expenses through 2025. As someone who frequently travels for work (though my employer reimburses most expenses), I've been assuming the old rules were still in place. @fd802658100b, I'm sorry your upgrade isn't deductible, but at least you found out before filing! This is a great reminder for all of us to stay current on tax law changes. The TCJA really did reshape a lot of common deductions that people took for granted. One follow-up question for the group: if someone is self-employed or an independent contractor rather than a W-2 employee, would the upgrade fee potentially be deductible as a business expense on Schedule C? I'm thinking the rules might be different for business owners versus employees when it comes to mixed personal/business travel expenses.