This might be a stupid question but how much is the penalty for early withdrawal if I don't qualify for a waiver? I took out about $7,000 from my IRA last year but I can't figure out if it's worth going through all this hassle with Form 5329 or if I should just pay the penalty.

I had a similar TurboTax nightmare last year with Form 5329! The software definitely has bugs with the hardship waiver sections. One thing that worked for me was manually preparing Form 5329 using the PDF version from the IRS website and filing it separately. It's actually pretty straightforward once you have the paper form in front of you - just fill in Part I with your distribution amount and check the appropriate exception code for medical hardship. For the hardship explanation, attach a separate statement with details about your medical situation and any supporting documentation you have (medical bills, doctor's notes, etc.). The IRS instructions say to "attach an explanation" so a typed letter works fine. Since you're close to the deadline, I'd recommend filing your 1040 now to get your refund, then send the Form 5329 separately within the next few days. Just make sure to sign it, date it, and include your SSN at the top. If you owe additional tax from the form, include payment or use IRS Direct Pay online. Don't let the software hold up your entire return - the separate filing option exists exactly for situations like this!

10 Quick question - does anyone know if student loan debt counts as a liability for the insolvency calculation? I have about $45k in federal student loans that were in deferment when my debt was canceled.

This is really helpful information! I'm dealing with a similar situation where the IRS is claiming I owe taxes on discharged debt from a few years ago. Your insolvency calculation looks solid - the fact that your liabilities exceeded your assets by $20,000 when the $15,500 debt was canceled should definitely qualify you for the full exclusion. One thing I learned from my tax preparer is to make sure you're using fair market values for your assets, not what you originally paid. So for your home and car, use the actual market value on the date the debt was canceled, not the purchase price. Also double-check that you included ALL liabilities - credit cards, student loans, any outstanding bills, etc. The documentation is key. I'd recommend creating a detailed spreadsheet showing every asset and liability with supporting documentation. The IRS loves paper trails, so bank statements, property records, loan statements - anything that backs up your numbers will help your case.

Hey, are you using TurboTax by any chance? I ran into that EXACT SAME ISSUE last week. The solution was to go to Forms Mode (you can search for it in the search bar at the top), then find Form 2210, and there's a checkbox that says "I didn't file this form last year" - check that and the software will stop asking for the missing info! Also, just a heads up that when you switch from MFJ to MFS, some of your deductions will be different. Make sure both of you don't claim the same credits for the kids. And double check your student loan interest deduction - when filing MFS, you usually can't claim that deduction (though the payment benefits might still make MFS worth it).

I had this exact same issue when I switched from MFJ to MFS three years ago! The tax software kept insisting I needed Form 2210 data from the previous year even though we'd never filed one. Here's what worked for me: First, double-check your 2022 return by searching the PDF for "2210" like others mentioned. If it's not there, you're good. Then in your tax software, look for an "interview mode" or "easy step" option and switch it OFF - go to the more detailed/advanced mode instead. This usually gives you more control over these yes/no questions. In the advanced mode, when it asks about Form 2210, there should be a clear "No, I did not file this form" option rather than just trying to skip past it. If you're still stuck, try starting a completely fresh return in the software and being very deliberate about answering "No" to the Form 2210 question the first time it appears. One more tip - make sure you're entering your 2022 AGI correctly from your actual tax return (not from memory). Sometimes the software gets confused if there's a mismatch and starts asking for forms you didn't file. Good luck finishing up before your extension deadline!

After reading all this, I'm genuinely curious - has anyone successfully used the 65-day rule to reduce trust taxes? My accountant mentioned it but wasn't sure if it was worth the effort for our situation.

This is incredibly helpful information! I'm dealing with a similar trust situation for my nephew and had no idea about the 65-day rule or the DNI calculations. One question - when you pay the taxes from the trust accounts, do you need any special documentation for the investment companies? I'm worried about how to properly record the tax payments as trust expenses versus personal expenses when I'm writing checks from the trust account. Also, has anyone dealt with estimated quarterly payments for trusts? I'm wondering if I should be making those going forward since we'll likely have similar investment income each year.

I went through this exact same situation last year and can confirm what others have said. The IRS publications really are confusing on this point, but the key is understanding that "space within the living area" gets special treatment. Here's what I did based on advice from a tax attorney: 1. **Form 8949**: Reported the entire house sale here, claimed my $250k primary residence exclusion 2. **Schedule 1, Line 8z**: Reported all depreciation I had claimed over the 8 years I rented out two bedrooms The depreciation recapture was about $18,000 in my case, which got taxed as ordinary income at 25%. What surprised me was that I could still claim the full primary residence exclusion on the remaining gain, even though I had been renting out rooms. One thing I wish I had known earlier - if you made any capital improvements specifically to the rented rooms (like adding a bathroom or upgrading flooring just for those rooms), you might be able to add those to your basis calculations. It's worth reviewing your records for any room-specific improvements. Also, double-check that you've been consistently using the same percentage for depreciation each year. The IRS will expect your recapture calculation to match what you actually claimed on your Schedule E forms.

I'm dealing with a very similar situation right now - sold my primary residence last year after renting out a basement apartment for 6 years. The confusion around Publication 523 is real! What helped me understand it was realizing that the IRS is trying to simplify things for homeowners who rent space within their primary residence. You don't have to do the complex allocation between personal and rental use that you'd need for a separate rental property. Here's my understanding based on research and consultation with a CPA: **For your situation (rooms within the house):** - Report entire sale on Form 8949/Schedule D - Claim your $250k primary residence exclusion - Report depreciation recapture on Schedule 1, Line 8z as ordinary income **Key point:** The depreciation recapture can't be excluded under Section 121, so you'll pay ordinary income tax on that portion (maxed at 25%). One thing I learned is to make sure you have good documentation showing exactly how you calculated the rental percentage each year. I used square footage, but some people use room count or other methods. Just be consistent. The good news is that even with the depreciation recapture, you still get to use the primary residence exclusion on the rest of your gain, which can save thousands in taxes compared to treating it as a pure rental property sale.