The Taxpayer Advocate Service sounds interesting - do you know how long it typically takes to get help from them? And would they be able to help with e-filing specifically or just general tax issues?

The Taxpayer Advocate Service typically takes 2-4 weeks to get assigned to your case, but they're absolutely able to help with e-filing issues, especially when there are technical barriers preventing you from filing correctly. They're particularly helpful in situations like yours where you're actively trying to comply with tax obligations but facing system limitations. For faster assistance, I'd recommend trying the solutions others mentioned first (different software or calling the IRS directly). The Taxpayer Advocate is great as a backup option if those routes don't work out. They can sometimes expedite processing of paper-filed amended returns in cases where e-filing isn't possible.

This is the correct answer! The IRS systems require a value for prior year AGI even if you didn't file. Using $0 is the standard workaround.

Does that QCD strategy help if you're not taking RMDs yet? I'm only 42 but I do donate about $3,000 a year to my church.

Unfortunately, the QCD strategy only works if you're at least 70.5 years old and are withdrawing from IRAs. At 42, your charitable donations would be itemized deductions rather than AGI reducers, and they go on Schedule A rather than directly reducing line 11. However, there is a strategy that might work for you - if you have a small business or freelance income, you might be able to structure some of your charitable giving as business sponsorships, which could be business expenses that reduce your AGI. This only works if there's a legitimate business purpose though, like advertising or promotion for your business.

Yes! I did this last year. If you're self-employed and not eligible for coverage through an employer (yours or spouse's), you can deduct 100% of your premiums. For me that was about $14,000 for my family plan! It's an adjustment to income on Schedule 1, so it directly reduces AGI.

I've always been told box 5 > box 1 = taxable income. Are you saying that's not necessarily true? I'm now wondering if I've been overpaying my taxes all these years by reporting scholarship income that maybe wasn't actually taxable.

Does the IRS actually audit people over unreported scholarship income? I'm not trying to avoid paying what I owe, but I'm in a similar situation to OP and now worried about the past 4 years.

I've had good experiences with FreeTaxUSA for scholarship situations. It asks specific questions about how the scholarship money was used rather than just comparing box numbers. Much better than TurboTax for this specific situation, and it's way cheaper too.

Thanks for the recommendation! I'll definitely give FreeTaxUSA a try next year. It's frustrating that TurboTax couldn't handle this properly - especially since we paid for their "premium" version specifically because my son had education tax forms. Appreciate you sharing your experience!

Thank you for mentioning this option. I had no idea tax debt could be discharged through bankruptcy. Is that something that applies to all types of tax debt or just income tax? And did it affect your credit score as badly as people say?

Bankruptcy can only discharge income tax debt, not payroll taxes, fraud penalties, or certain other types. The debt needs to be from a return that was due at least 3 years ago, filed at least 2 years ago, and assessed by the IRS at least 240 days ago. Yes, bankruptcy did impact my credit score - it dropped about 150 points initially. However, it's already started recovering, and the relief of not having that massive tax debt hanging over me was worth it. I've been able to start rebuilding my credit, and some lenders actually see me as a better risk now because my debt-to-income ratio is so much better without the tax debt. I recommend at least having a consultation with a bankruptcy attorney who specializes in tax issues. Many offer free initial consultations, and they can tell you exactly which portions of your tax debt might be dischargeable.

Were you able to get your penalties reduced too? I've heard the IRS sometimes gives "first time abatement" but wasn't sure if that applies when you've already been on payment plans.

This is such an important distinction! I messed this up one year and it was a nightmare to fix. Quick question - if you have access to both an HSA and FSA (limited purpose FSA), can you contribute to both in the same year? My benefits coordinator gave me conflicting info.

Yes, you can contribute to both an HSA and a Limited Purpose FSA in the same year. The key is that it must be a "Limited Purpose" FSA that only covers dental and vision expenses, not a regular medical FSA that covers all healthcare expenses. Regular medical FSAs would make you ineligible for HSA contributions, but the Limited Purpose FSAs are specifically designed to work alongside HSAs. This combination actually gives you the most tax advantages, as you can use the Limited Purpose FSA for immediate dental/vision needs while letting your HSA investments grow for future medical expenses.

The limits for 2024 are higher just fyi: - $4,150 for individual coverage - $8,300 for family coverage Plus still the +$1,000 for 55+ folks

Is the contribution limit per calendar year or plan year? My company's health plan runs July-June but taxes are Jan-Dec. Always confuses me when figuring the max I can contribute.