Has anyone used Free File Fillable Forms to handle this? I'm trying to do my own taxes with backdoor Roth for the first time and I'm completely lost on how to properly report everything.

I went through this exact same situation last year and want to share what I learned! You're absolutely right to be concerned - taking the deduction when doing a Backdoor Roth creates a tax mess. Here's what happened in your case: You deducted the Traditional IRA contribution (getting a tax benefit now), but then converted that pre-tax money to a Roth IRA. The IRS sees this conversion as taxable income since you're moving pre-tax dollars into an after-tax account. If you didn't report the conversion as income on your return, you definitely need to amend. You have two paths forward: 1. Keep the deduction and add the conversion as taxable income on an amended return 2. Remove the deduction, file Form 8606 for a non-deductible contribution, and the conversion won't be taxable For future reference, the classic Backdoor Roth strategy uses option 2 - make non-deductible contributions specifically so the conversion isn't a taxable event. Since you were eligible for the deduction (no employer plan), you had to actively choose NOT to take it. I'd recommend consulting with a tax professional before amending, as they can run the numbers to see which option saves you more in taxes. The timing matters too since amended returns take months to process.

Has anyone successfully used a GRAT with cryptocurrency? I've got a client with substantial ETH holdings who's interested in using a GRAT to transfer future appreciation to his kids, but I'm concerned about the valuation challenges and volatility issues.

This is such a timely discussion! I'm a tax attorney who's been working with GRATs for about 8 years, and I've seen their popularity absolutely explode since interest rates dropped. One thing I'd add to the excellent technical discussion here is that GRATs work particularly well in today's environment because the IRS 7520 rate (currently around 5.2%) is still relatively favorable for wealth transfer strategies. When you can reasonably expect assets to appreciate faster than that rate, the math becomes very compelling. For anyone considering a GRAT, I always recommend thinking about it as part of a broader wealth transfer strategy. We often pair them with sales to intentionally defective grantor trusts (IDGTs) or charitable lead annuity trusts (CLATs) depending on the client's goals. Also worth noting - while the Biden administration proposals haven't moved forward yet, there's still political appetite for GRAT reform. If you're on the fence about implementing one, the current rules might not be around forever. The proposed 10-year minimum term and minimum remainder value requirements would significantly reduce their effectiveness. Has anyone here dealt with IRS audits of GRAT valuations? I'm curious about others' experiences with the Service challenging initial asset valuations, especially for hard-to-value assets like private company interests.

Has anyone here successfully claimed a refund for Social Security taxes that were incorrectly withheld during their first two years on a J1? My university withheld FICA taxes from my first paycheck in 2023 all the way through 2024, and I only recently learned I shouldn't have been paying these taxes during that time. I've heard you can file Form 843 "Claim for Refund and Request for Abatement" along with a statement from your employer, but I'm wondering if anyone has actually gone through this process successfully.

I went through this exact same situation last year! I'm a J1 research scholar from India, and my university started withholding Social Security taxes in January 2024 after I had been exempt for my first two calendar years (2022-2023). What really helped me understand the timing was learning that the IRS counts any part of a calendar year as a full year for the exemption. So even though you only arrived in September 2023, that counts as your first year, 2024 as your second, and now 2025 is when the exemption ends. One thing to double-check is whether India and the US have a totalization agreement that might affect your situation. India doesn't have one with the US, so I definitely had to start paying once my exemption period ended. But since you mentioned you're from Brazil, and I saw in the comments that Brazil does have a totalization agreement, you might want to look into whether you can get a certificate of coverage from Brazilian social security authorities. Also, make sure your university is correctly calculating this. Some payroll departments make mistakes with international employees. I'd recommend getting a written explanation from them about why they're starting the withholding now, just to have it documented.

Quick question - I'm also in Denver and planning to sell a rental soon. Does anyone know if 1031 exchanges are harder to complete now with the tight real estate market? My concern is finding a replacement property in time.

Based on what everyone has shared here, it sounds like you're getting good advice from your accountant. The $187k gain will definitely impact your AGI, which could affect various tax credits and deductions you currently qualify for. One thing I'd add that hasn't been mentioned yet - make sure you're accounting for any improvements you made to the rental property over the years. Those can be added to your cost basis and reduce your taxable gain. Things like new roof, HVAC system, flooring, kitchen renovations, etc. Many people forget to include these when calculating their capital gains. Also, since you mentioned you've owned since 2017, don't forget about depreciation recapture if you've been claiming depreciation on the property. That portion gets taxed at 25% rather than the regular capital gains rates. Given the complexity and the large amount involved, it might be worth paying for a consultation with a tax professional who specializes in real estate transactions before you finalize the sale. They can run the numbers on different scenarios and help you understand exactly what credits you might lose and whether any timing strategies make sense for your situation.

Anybody else notice the Where's My Refund tool is basically useless these days?

Just want to add that if you're approaching day 21 and getting nervous, check if you claimed any credits like EITC, CTC, or AOTC. Those automatically add extra processing time (usually takes the full 21 days minimum). Also make sure your bank info is correct - a lot of delays happen because of wrong account numbers or closed accounts.