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.

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.

This is really helpful! I didn't know about this grouping election at all. Where exactly do I make this election? Is it something I need to file separately or is it part of the regular tax forms?

You make the grouping election by attaching a statement to your tax return in the year you want to start the grouping. The statement should identify the properties you're grouping together and state that you're treating them as a single activity for passive activity purposes under Regulation 1.469-4(c). Once you make this election, it's binding for future years unless your facts and circumstances change significantly. The statement doesn't have a specific form - it's just a written declaration attached to your return. Many tax software programs don't prompt you for this, so you may need to create it separately and attach it as a PDF if filing electronically.

What tax software did you use when you got audited? I'm wondering if some programs flag these deductions more than others.

I used TurboTax when I got audited. I don't think it was the software that triggered the audit though - from what the auditor told me, it was more that claiming real estate professional status with significant losses is just a common audit trigger, especially with higher household income. The auditor specifically looked for contemporaneous documentation - meaning records created at the time I did the work, not reconstructed later. They were suspicious of round numbers (like exactly 4.0 hours) and wanted to see variation in my time logs to make them seem more authentic. My recommendation: keep a daily log using a time-tracking app or detailed calendar entries.

7 I had a similar issue and found my W-2 in my Paycor account even though my employer said they "weren't ready yet." How would the original poster know if they have access? Is there a standard login page or something?

4 Yes, Paycor has a standard employee self-service portal at secure.paycor.com where employees can log in. If your employer set it up, you would have received an email invitation at some point to create your account. Even former employees typically retain access to their documents for a period after leaving. If you never set up an account, you can try the "forgot password" option using your work email, or call Paycor's employee support line at 800-381-0053 and ask if you have an account associated with your employer. Sometimes they can help reset access if you can verify your identity.

14 I reported a former employer two years ago. Called the IRS W-2 complaint line, gave all the details, and about 2 weeks later the employer suddenly emailed W-2s to everyone with a very apologetic note. Heard through a friend still working there that they got hit with some decent fines. Definitely worth reporting!

Thanks so much for breaking this down! This makes way more sense now. I found my tax return and my AGI was actually $48,500, so my adjustments were about $7,500 and then the standard deduction took me down to the $35k taxable income. Do you know what the income limits are for those education credits? I'm hoping to qualify next year.

For 2025 (taxes you'll file in 2026), the American Opportunity Credit begins to phase out at $80,000 MAGI for single filers and $160,000 for married filing jointly. It's completely phased out at $90,000/$180,000. The Lifetime Learning Credit has the same phaseout ranges. With your AGI around $48,500, you should be well within the limits to claim either credit as long as your income doesn't increase dramatically. The American Opportunity Credit is worth up to $2,500 but can only be claimed for the first 4 years of undergraduate education. The Lifetime Learning Credit is worth up to $2,000 and can be used for any level of education, including graduate courses or professional development.

Mortgage lenders will almost always look at your gross income (before any deductions) and sometimes specifically at your AGI, not your taxable income. They want to know your actual earnings capacity, not the number after all your deductions. They'll typically ask for 2 years of tax returns and recent pay stubs to verify your income.