Has anyone used TurboTax to file back taxes? I'm in this exact situation and wondering if the regular tax software works for previous years or if I need something special.

Don't beat yourself up about this - you're definitely not alone! I work as a tax preparer and see this situation all the time, especially after the past few years with all the economic uncertainty. Here's what I always tell my clients in your situation: Yes, there will be penalties and interest, but the IRS is actually pretty reasonable when you're proactive about fixing things. The failure-to-file penalty is much worse than the failure-to-pay penalty, so getting those returns submitted should be your absolute top priority even if you can't pay everything right away. A few practical tips: Start with gathering your documents for both years. If you're missing W-2s or 1099s, you can request wage and income transcripts from the IRS website for free. Once you file, you can absolutely set up a payment plan - the IRS offers installment agreements up to 72 months for balances under $50,000, and the setup fee is pretty reasonable. Also, don't assume you owe exactly what you calculated. You might be missing deductions or credits that could reduce what you owe. I've had clients who thought they owed thousands but ended up owing much less (or sometimes even getting refunds) once we properly prepared their returns. The key is just to start the process. Every day you wait, the penalties and interest keep adding up. You've got this!

This thread has been incredibly helpful! I'm dealing with a similar Box 18/19/20 issue and wanted to share what worked for me after trying several of the suggestions mentioned here. I ended up using a combination of approaches: first, I checked my state's Department of Revenue website to find the official locality naming format (as Kelsey suggested), then cross-referenced it with my physical work location. For my situation in Cook County, Illinois, I needed to use "COOK COUNTY" rather than just "Cook County" - the all-caps format made all the difference in getting my tax software to accept it. What really sealed the deal was calling my local tax office directly (thanks Victoria for that tip!). They confirmed that my employer should have been withholding local taxes, so Box 19 being empty was indeed an error. They also walked me through exactly what to enter in my tax software while I waited for a corrected W-2. For anyone still struggling with this: don't be afraid to make that call to your local tax office. I was dreading it, thinking I'd be on hold forever, but I actually got through in about 15 minutes and the person was super knowledgeable about these W-2 formatting issues. The key lesson I learned is that Box 18/19/20 problems are way more common than I thought, and there are definitely people out there who can help you figure it out. Don't suffer in silence with confusing tax software error messages!

This has been such an educational thread! I'm a newcomer here but have been lurking and dealing with a very similar W-2 issue. Reading through all these responses has been incredibly reassuring - I had no idea how common Box 18/19/20 problems actually are. What I found most helpful was the multiple approaches people shared: checking state Department of Revenue websites for official locality formats, calling local tax offices directly, trying different tax software if one isn't working, and considering the VITA program for free help. It's great to see a community where people share practical solutions instead of just complaining about the problem. One thing I'm taking away from this discussion is that it's really worth the effort to get a corrected W-2 if your employer made an error, especially if you're looking at owing a significant amount in local taxes that should have been withheld. The extension route seems like a smart approach if you have the time to wait for the correction. Thanks to everyone who contributed - this thread should be bookmarked for anyone dealing with W-2 local tax issues!

Have you considered what might happen if you make financial plans based on receiving the full amount? The transcript shows what the IRS has approved, but have you verified what will actually reach your bank account? Many taxpayers are surprised when their deposit is smaller than expected due to this exact situation. Could you contact your state's child support enforcement agency directly to confirm the offset amount? They often have this information before it appears in any federal system and might give you a more accurate picture of what to expect.

I experienced this exact same situation two years ago and it was incredibly confusing at first! Your transcript is showing the full amount because that's what the IRS processed and approved - but here's the key thing everyone's touching on: the child support offset happens at the Treasury level, not the IRS level. What I learned is that you should definitely NOT count on receiving the full amount shown on your transcript. The Treasury Offset Program will intercept whatever you owe for back child support before the money reaches your bank account. The frustrating part is that this offset won't show up on your IRS transcript because it's handled by a completely different agency (Bureau of Fiscal Service). My advice? Contact your state's child support enforcement office directly - they can usually tell you exactly how much will be offset before you even receive your deposit. That way you can plan accordingly instead of being surprised when a smaller amount hits your account. The offset notice from Treasury typically arrives after your deposit, which doesn't help with planning!

Don't forget about the primary residence exclusion! If this was your brother's primary residence for at least 2 of the 5 years before the sale, he might qualify to exclude up to $250,000 of gain from his income (or $500,000 if married filing jointly). Based on what you described, he lived there for about 2 years before moving out 2 years ago, so he might just barely qualify if the timing works out exactly. This could potentially eliminate any tax liability from the sale, even if he has to report it.

This is definitely a tricky situation that requires careful documentation. From what you've described, your brother needs to report the sale even though he didn't receive proceeds from the actual sale, because he was still legally on the deed. The key is treating this as a two-part transaction: (1) the original buyout he received when they split up, and (2) the formal sale that just happened. On Schedule D, he should report the sale with his cost basis being the original purchase price plus improvements, and his proceeds being only the buyout amount he received years ago (not the recent sale proceeds). You'll definitely want to include a detailed explanation with the return describing the situation. Also, try to get documentation of the original buyout agreement if possible - this will support your position if the IRS has questions. One important thing to check: make sure you understand whether he received a 1099-S form. If he did, the IRS will be expecting to see this sale reported. If the ex-girlfriend also reports part of the sale, you want to make sure there's no double-reporting of the same income.

Has anyone tried the IRS's W-4 calculator? I think it's free and supposedly helps you figure out proper withholding based on multiple jobs. Wondering if it would solve part of your problem at least for the W2 portion?

I've been dealing with a similar situation - multiple income streams including S-corp income can really mess with your withholding calculations! One tool that's worked well for me is FreeTaxUSA's TaxCaster. It's free and handles S-corp salary vs distribution scenarios better than most consumer tools I've tried. The key thing I learned is that you need to track your S-corp salary as regular W-2 income for withholding purposes, but then account for the self-employment tax savings compared to if that income was straight 1099. Most calculators miss this nuance. Also, don't sleep on making quarterly estimated payments - even if your withholding is close, having that extra buffer from estimated payments can save you from underpayment penalties. I set up automatic transfers to a separate "tax savings" account so the money is there when quarterly dates roll around. The IRS safe harbor rule is your friend too - if you pay 100% of last year's tax liability through withholding + estimated payments (110% if your AGI was over $150k), you won't owe penalties even if you end up owing more at filing time.