I might be the minority here but I actually prefer doing my backdoor Roth in December and January of the same tax year to avoid this exact reporting confusion. Contribute to Traditional in early December, then convert to Roth before December 31st. That way everything happens in the same tax year and you get the 1099-R in time for filing season.

Just want to add one more thing that might help others in this situation - when you do file your 2024 taxes with Form 8606 to report the non-deductible contribution, make sure to keep a copy of that return AND the 8606 form in your tax records. You'll need to reference it next year when filing your 2025 taxes to show the IRS your basis calculation for the conversion. I learned this the hard way when I couldn't find my old 8606 and had to reconstruct the numbers. The IRS can get confused about basis if you don't have clean documentation showing the progression from contribution to conversion across tax years.

@Nina Fitzgerald I actually went through this exact same situation a few months ago! The phone number everyone's mentioning (1-800-830-5084) is definitely your best bet. I'd recommend calling right when they open at 7 AM - I got through in about 15 minutes that way. One thing I learned: make sure you actually NEED to cancel vs. just reschedule. If you still need identity verification but just can't make that specific time, rescheduling might be easier than starting the whole process over. The agent will ask you why you're canceling, so be ready to explain. Also, don't stress too much about it - the IRS agents are usually pretty understanding about appointment changes. Just have your SSN and the appointment confirmation info ready when you call. You got this! 👍

I've been through this process recently and it's definitely frustrating! The phone route is really your only option since there's no online cancellation system (which is honestly ridiculous in 2024). A few things that helped me: - Call 1-800-830-5084 as others mentioned - Have your appointment confirmation number ready along with your SSN - If you get disconnected or can't get through, don't give up - it took me 3 tries over 2 days - Ask for a cancellation confirmation number or email if possible One important thing to consider: Are you canceling because you no longer need identity verification, or just because of scheduling conflicts? If it's the latter, rescheduling might be easier than starting over if you still need to complete the verification process eventually. The whole system is outdated but the agents are generally helpful once you get through. Hang in there! 💪

Has anyone used their betting app's year-end summary as documentation for losses? My FanDuel account has a tax document that shows my total deposit, withdrawals, winnings and losses. Wondering if that's enough for the IRS?

I went through this exact same situation last year with my Venmo 1099-K from sports betting. The stress was real! Here's what I learned after consulting with a tax professional: 1. Yes, you do have to report the full $7300 as gambling income on your tax return, even though it includes your original deposits. 2. You can deduct your gambling losses (the $4700 you put in) but ONLY if you itemize deductions on Schedule A. This means you can't take the standard deduction. 3. The key decision is whether itemizing saves you more money overall than taking the standard deduction. For 2024, the standard deduction is $14,600 for single filers. If your gambling losses plus other itemizable deductions (mortgage interest, state taxes, charitable donations, etc.) exceed that amount, then itemizing makes sense. 4. Keep ALL your records - bank statements showing transfers, screenshots of betting account activity, and any year-end statements from your betting apps. The unfortunate reality is that if itemizing doesn't benefit you, you could end up paying taxes on the full $7300 rather than just your $2600 profit. This is a common frustration for casual gamblers. Consider talking to a tax pro if the numbers are significant - sometimes the consultation fee is worth it for peace of mind and making sure you're handling everything correctly.

One thing to consider with mortgage payoffs before a 1031 exchange that nobody's mentioned yet - if your existing mortgage has a prepayment penalty, that penalty is NOT considered part of your exchange basis. I found this out the hard way and ended up with a $3,800 penalty that I couldn't roll into the 1031. Check your mortgage terms carefully!

This is a really thorough discussion! Just wanted to add one more consideration that might be relevant - the timing of when you actually pay off the mortgage versus when you start the 1031 exchange process. I'm dealing with a similar situation right now and my qualified intermediary advised me to coordinate the mortgage payoff timing carefully with the exchange timeline. If you pay off the mortgage too far in advance of listing the property, it could raise questions about your intent to do a 1031 exchange from the beginning. The IRS likes to see that your 1031 exchange was planned as part of an investment strategy, not something you decided to do after the fact. So while paying off the mortgage before the exchange is totally fine from a tax perspective (as others have confirmed), just make sure you can document that the 1031 was always part of your plan. My QI suggested keeping records showing I was researching replacement properties and consulting with them before paying off the mortgage, just to establish the timeline clearly. Probably overkill, but better safe than sorry with the IRS!

When I had a similar W2c issue, TurboTax had a specific section for entering W2c information. Is anyone using a particular tax software that handles this well? My accountant charged me extra last year because of all the corrected forms and I'm trying to DIY this year.

I went through this exact same situation two years ago! The key thing to remember is that the W2c completely replaces the information on your original W2. You should only use the corrected information when filing - so yes, use code W with the $13,340 amount. The reason for the code change makes total sense too. Code D is for your own 401(k) deferrals (money taken out of your paycheck), while code W is for employer HSA contributions (money your company puts into your HSA account). Your payroll department probably miscoded it initially. One thing that helped me was calling my HR department to confirm what actually happened. In my case, they had incorrectly categorized the employer's HSA contribution as a 401(k) deferral on the original W2. The good news is that employer HSA contributions (code W) are generally more favorable tax-wise since they don't count as taxable income at all. Make sure whatever tax software you're using has an option for entering W2c information specifically - don't just manually change the numbers from your original W2 entry.