Just went through this with my tax guy and apparently it's super common for Box 7 to be unchecked, especially with loans that have been sold between servicers. My tax preparer said as long as you know it's your primary residence, you just check that box on Schedule A when entering your mortgage interest deduction and keep moving. The only time to worry is if you're trying to deduct interest on a property that isn't your primary or secondary residence, or if you're deducting interest on more than two properties. Then you might run into limitations or need to provide additional documentation.

Most major tax software like TurboTax, H&R Block, and TaxAct handle the Box 7 issue automatically when you input your mortgage interest information. You typically just enter the amount from Box 1 of your 1098, and the software assumes it's for a qualified residence unless you specify otherwise. If you're using TurboTax, it will ask you questions about the property (like "Is this your main home?") rather than specifically asking about Box 7. As long as you answer that it's your primary residence, the software will properly categorize the deduction regardless of what's checked on the form. The Box 7 checkbox is really more for the IRS's information processing than for your tax preparation. Your software cares about the actual facts of your situation, not what boxes the lender checked or didn't check on the form.

Quick question - I have a settlement coming up for a car accident. I'm getting about $31k for my injuries and the insurance is paying my lawyer directly (about $12k). My lawyer said I won't owe taxes, but the insurance company mentioned something about sending a 1099. Should I be worried?

Based on what you've described, you're in a good position tax-wise. Since your settlement is specifically for physical injuries and the attorney fees are being paid separately and directly to your lawyer (not through you), you likely won't owe taxes on either portion. The key factors working in your favor are: 1) Physical injury settlements are generally tax-free under IRC Section 104(a)(2), and 2) Attorney fees paid directly by the defendant to your attorney aren't considered income to you. However, I'd recommend keeping detailed records of everything - the settlement agreement showing the separate payment structure, any documentation showing the attorney fees went directly to your lawyer's firm, and confirmation that this was purely for physical injuries with no punitive damages or other taxable components. If you want absolute certainty, consider having a tax professional review your specific settlement documents before filing. Every case has unique details that could affect the tax treatment.

This is such great timing! I was just about to start working on my 2022 taxes and was dreading the cost of tax software. I have a pretty straightforward situation - just W-2 income and standard deduction - so Free Fillable Forms sounds perfect for me. I really appreciate everyone sharing their experiences here. The tips about saving frequently and double-checking all the numbers are exactly what I needed to know. And it's good to hear that it stays available through the deadline since I'm definitely more of a March filer than a February filer! One thing I'm curious about - for those who've used it multiple years, do you find it gets easier the second time around? I'm wondering if I'll remember the process better next year or if it's still going to feel like starting from scratch each time.

This is super helpful! I've been using TurboTax for years but my situation is pretty straightforward (W-2, some interest income, standard deduction) and I'm tired of paying $60+ every year for something I could probably do myself. The tip about making a list of needed forms from last year's return is brilliant - I never would have thought of that. And good to know about the math limitations, especially around the actual tax calculation. I'm comfortable with basic math so that shouldn't be a problem. Quick question for anyone who's made the switch from paid software - did you feel like you missed out on any deductions the first year you switched to Free Fillable Forms? That's my biggest worry about doing it myself.

Has anyone used TurboTax Business to file their single-member S corp return? Can it handle the K-1 generation properly? I'm trying to decide between doing it myself or paying my accountant $950 to file it all.

I went through this exact same situation when I formed my single-member S corp two years ago. Yes, you absolutely need to issue yourself a Schedule K-1 even though you're the only shareholder. The S corporation is a pass-through entity, so all income, deductions, and credits flow through to you as the owner via the K-1. Think of it this way: your W-2 shows the salary you earned as an employee of the corporation, while the K-1 shows your share of the business profits/losses as the owner. These are two different capacities - employee vs. shareholder - so you need both forms. The K-1 will report things like your share of ordinary business income, any rental income if you have it, business deductions that pass through to your personal return, and various credits. Make sure when you prepare the 1120-S that you're consistent between what's reported on the corporate return and what flows to your K-1. The IRS matches these up, so any discrepancies will trigger questions.

This is exactly the kind of situation where understanding the safe harbor rules can save you a lot of stress! You're absolutely right about the basic concept, but as others have mentioned, there's that important income threshold to consider. Since your 2024 AGI was well above $150k, you'll need to hit 110% of your prior year tax liability ($120,460) rather than 100%. The good news is that your projected withholdings of $148,557 put you well above that threshold, so you should be completely protected from underpayment penalties. One thing I'd suggest is documenting your safe harbor calculation and keeping a record of your withholding progression throughout the year. This way if there are ever any questions from the IRS, you have a clear paper trail showing you met the safe harbor requirements. Also, while you mentioned you're comfortable with the large tax bill in April, you might want to consider whether having that much cash tied up until tax time affects any other financial planning you're doing. Some people prefer to increase withholdings slightly to reduce that final bill, but it's totally a personal preference since you're already penalty-protected. Sounds like you've done your homework and are in great shape! It's always nice when the tax code actually works in your favor for once.

For documenting your safe harbor calculation, I'd recommend keeping these key records: 1. **Prior year tax return** - specifically line showing your total tax liability ($109,509 in your case) 2. **Safe harbor calculation worksheet** - showing the 110% calculation ($120,460) with your AGI confirmation from 2024 3. **Monthly withholding tracking** - I keep a simple spreadsheet with each pay period's federal withholding and running year-to-date total 4. **Final Form W-2s** - these will show your total withholdings for the year Regarding other IRS interactions with income jumps - you might see some automated notices if there's a big discrepancy between years, but they're usually just informational. The IRS computer systems sometimes flag large changes and send letters asking you to verify income or deductions, but as long as everything is legitimate and well-documented, it's not a problem. One heads up - if your income jump pushes you into AMT (Alternative Minimum Tax) territory, that can add complexity to your calculations. The safe harbor rules still apply, but your actual tax liability calculation becomes more involved. Might be worth having a tax professional review your situation if you haven't already, especially with income changes this significant. You're definitely on the right track though! Having $148k in withholdings against a $120k safe harbor requirement gives you great protection.