I used TurboTax last year and it handled the 1099-B import fine, but it doesn't really explain wash sales well. It just takes whatever wash sale adjustment your broker reports. If you disagree with your broker's calculation (like OP's situation), TurboTax won't help you figure that out - you'd need to make manual adjustments. I switched to TaxAct this year and it seems to handle it a bit better with more explanations about the wash sale calculations.

Thanks for the info about TurboTax. I'm concerned about the imports because my broker (Fidelity) sometimes categorizes things differently than TurboTax expects. I hadn't considered TaxAct - might check that out instead. Really just want something that will handle the calculations correctly without me having to become a wash sale expert. The whole "substantially identical securities" thing gets really confusing especially with ETFs that have overlap.

Yes, buying in your IRA after selling at a loss in your taxable account does trigger a wash sale! This is a common misconception. If you sell a security at a loss in your taxable account and purchase the same or "substantially identical" security in your IRA (Roth or Traditional) within 30 days before or after, the wash sale rule applies. What makes this particularly painful is that when the loss is disallowed due to an IRA purchase, that loss is essentially lost forever since you can't adjust the cost basis in an IRA.

And if the food truck LLC has inventory, you might need to account for cost of goods sold on your Schedule C. This is super important for food businesses since your ingredients and supplies are considered inventory.

I did try contacting them first actually! Their payroll person said they'd "look into it" about two weeks ago but I still haven't received anything. That's why I'm trying to figure out how to work around it in TurboTax since the filing deadline is getting closer.

That's frustrating! If you've already tried contacting them, I'd recommend following up one more time with a deadline - something like "I need this corrected by next Friday to file my taxes on time." Sometimes that creates more urgency. In the meantime, the workaround suggested by others is your best bet. Enter it exactly as shown on the form (so dollar amounts match IRS records) but add detailed notes explaining the discrepancy. The total income reported is what matters most from a tax calculation perspective.

I work with taxes (not a professional, just at a community volunteer center) and see this kind of thing often. Generally, the IRS is concerned with whether all income is reported, not necessarily which box it appears in on a 1099. As long as you include the income and document the discrepancy, it rarely causes problems.

I tried the import option initially, but my broker (a smaller one) isn't supported for direct import. Plus I had some employee stock options that got reported weirdly. Would this still work in my situation or am I stuck with the mail-in option?

If your broker isn't supported for direct import, then unfortunately you're likely stuck with either manual entry or the summary/mail-in option. Employee stock options add another layer of complexity too. In your specific situation, I'd probably go with what you're doing - e-file the main return with the summary on Form 8949 and Schedule D, then mail Form 8453 with your detailed records. Just make sure to keep copies of everything you send. Next year, you might consider switching to a more widely-supported broker if electronic filing is important to you.

Does writing your SSN on every page actually matter? Seems excessive and kind of risky from a identity theft perspective.

7 That sounds terrifying! How long was his bankruptcy and how much extra time did it add to the collection period? I'm wondering because I did a Chapter 13 a few years ago and now I'm worried about my tax debts.

14 His bankruptcy added almost 3 years to the collection period. The CSED clock stops completely during the bankruptcy plus 6 months afterward. His Chapter 7 lasted about 8 months, but with the additional 6-month suspension, that's 14 months total that got added to his 10-year period. Chapter 13 bankruptcies typically last 3-5 years, so that could potentially add a substantial amount of time to your collection period. I'd definitely recommend getting your transcripts and having someone calculate your actual CSED dates taking the bankruptcy into account.

17 Yes, the IRS often becomes more aggressive with collection actions as the CSED approaches. Filing a Notice of Federal Tax Lien is definitely something they consider when the clock is running out. The important thing to understand is that even if they file a lien shortly before the CSED expires, the lien should self-release when the collection statute expires.