Does anyone know if TurboTax handles this better than FreeTaxUSA? I'm in the same boat with about 50 transactions and a couple wash sales. Would switching tax software make this easier?

I've been dealing with this exact same issue! For what it's worth, I called my brokerage (Charles Schwab) directly and they were able to provide me with a supplemental report that breaks down exactly which transactions had wash sales applied. It turns out most brokerages can generate this detail if you ask - it's just not included in the standard 1099-B. Once I had that breakdown, I was able to use the summary method for about 80% of my transactions and only had to list the specific wash sale transactions individually with code W. Saved me hours of data entry and I felt confident I was reporting everything correctly according to IRS rules. If your brokerage can't provide this detail, you might want to consider keeping better records next year or using a portfolio tracker that identifies wash sales in real-time as you trade.

Double check that the TIN (taxpayer identification number) on your 1042-S matches exactly what's on your 1040NR. I had a case where my university had an old ITIN for me on the 1042-S but I had since gotten an SSN and used that on my tax return. The IRS couldn't match them up even though all the dollar amounts were correct.

I've been through this exact situation and it's absolutely maddening! The good news is that these 1042-S matching issues are usually resolvable, but they do require some patience. A few things to check immediately: 1) Make sure your SSN/ITIN on the 1042-S matches exactly what you used on your 1040NR. Even if you recently switched from ITIN to SSN, if your withholding agent still has your old number on file, that could be the culprit. 2) Since you mentioned getting a reissued 1042-S, there's a real possibility that your withholding agent accidentally submitted BOTH versions to the IRS - the original and the corrected one. This would show up as duplicate reporting and could trigger the discrepancy notice. 3) When you contact your withholding agent, ask them specifically to verify: a) What version they submitted to the IRS, b) The exact dollar amount in box 7, c) Your name spelling and TIN as it appears on their submission. The IRS notice should include a phone number for questions about the discrepancy. While their phone lines are notoriously difficult to reach, if you can get through, they can tell you exactly what 1042-S information they have on file for you. This eliminates the guesswork about what went wrong. Don't panic - I've seen these resolved in the taxpayer's favor more often than not, especially when the amounts actually do match correctly like in your case.

Let me take a wild guess... student loans? That's what happened to me too. If it's federal student loans, look into getting on an income-driven repayment plan. That might be better than just paying the offset amount, especially if you qualify for the new SAVE plan. Most people don't realize you have options beyond just paying what they demand.

This exact thing happened to my brother-in-law last year! The timing issue between IRS refund processing and the Treasury Offset Program is surprisingly common. What basically happened is your refund got processed and sent out before the offset could be applied - it's like two different computer systems that don't talk to each other very well. You're absolutely doing the right thing by being proactive and calling TOP to set up a payment plan. From what I've seen, they'll usually send you a formal notice within 30-60 days demanding payment for the amount that should have been offset. The key is to not ignore it when it comes. One thing to keep in mind - if this is federal student loan debt, you might want to look into getting back on a regular payment plan or income-driven repayment plan with your loan servicer rather than just paying the offset amount as a one-time thing. That way you're actually addressing the underlying debt and potentially avoiding future offsets. Keep all your documentation from the calls you make and any letters you receive. This kind of bureaucratic mix-up can sometimes lead to confusion down the road, so having good records will save you headaches later.

Another perspective - consider whether it might actually work out better without the 83b in some scenarios. If your company's valuation tanks or grows very slowly, you might actually be better off without having made the election since you'd only be taxed on the actual value at vesting (which could be lower than projected). I've seen people rush to file 83b elections, prepay taxes on high valuations, then watch their companies fail and end up with worthless stock they already paid taxes on. Without the 83b, you're only taxed as value is realized through vesting. Not saying this helps with your current situation, but maybe a silver lining perspective if the company doesn't skyrocket as expected.

I hate to be the bearer of bad news, but the 30-day deadline for 83b elections is unfortunately set in stone. The IRS has been extremely consistent on this - there's no "reasonable cause" exception, no extensions, and no retroactive filings allowed. I've seen people try everything from medical emergencies to natural disasters as justification, and the IRS doesn't budge. Your situation is definitely frustrating, but you're not alone - this happens to a lot of startup employees who get caught up in the excitement of a new role. The good news is that while you can't undo the missed deadline, you can still manage the tax impact going forward. Start by getting a clear picture of your vesting schedule and the company's current valuation. You'll need to recognize ordinary income tax on the spread between your exercise price and fair market value at each vesting date. This means setting aside cash for taxes as shares vest - don't wait until year-end to deal with this. Consider making estimated quarterly tax payments to avoid underpayment penalties, especially if the tax hit will be significant. Also, keep detailed records of everything related to your equity grant - grant date, exercise price, vesting dates, and company valuations. You'll need this documentation for proper tax reporting. While missing the 83b election stings now, remember that it's only beneficial if the company value increases substantially. If growth slows or the company struggles, you might actually end up better off without having prepaid taxes on potentially overvalued equity.

Don't forget about state taxes too! Your 1099-B might not be taxable for federal purposes as a nonresident alien, but some states have different rules. For example, I'm in California and they consider certain capital gains taxable for nonresidents even when the feds don't. Check your state's rules or you might get a surprise tax bill later.

Just wanted to add another perspective as someone who went through this exact situation two years ago. The key thing that helped me understand was realizing that as a nonresident alien student, you're essentially in a "protected" category for most investment income. The IRS generally doesn't want to tax casual investment gains from nonresident students because you're not here permanently and aren't engaged in a U.S. trade or business. However, you still need to be careful about a few things: 1. Keep detailed records of your days in the US each year - this becomes crucial for both the substantial presence test and the special capital gains 183-day rule that Liam mentioned. 2. Don't forget about the FBAR (Foreign Bank Account Report) if you have foreign accounts with more than $10,000 aggregate balance at any time during the year. 3. Even if your capital gains aren't taxable, you might still want to attach a statement to your 1040NR explaining why you're not reporting them - this can prevent IRS questions later. The good news is that most F-1 students in their first few years don't have to worry about capital gains taxes, but the rules can get tricky if you stay longer or have substantial trading activity.