That's really good advice. I'm definitely going to make copies of everything. Do you know if I should be including my original tax returns with the response or just the supporting documentation for the head of household status?

Just include the supporting documentation for Head of Household status, not your entire original returns. The IRS already has your returns in their system. Focus on providing proof that you provided more than half the support for your mom and sister and that they lived with you. Include a copy of the notice they sent you with your response. Write your Social Security number on every page you send them. And definitely use certified mail with return receipt - that saved me when they tried claiming they never received my documents.

Yes, I filed Form 1040X for the amendment, but looking back at my copy, I see I checked the "Single" box on line 4 again. I was so focused on adding the dependents and credits that I completely missed changing the filing status. Rookie mistake I guess.

That explains exactly what happened then. When you amend a return, you need to check the correct filing status for your situation on Form 1040X, even if you're not changing your filing status from the original return. Since you were adding dependents, you should have updated to Head of Household. The good news is this is fixable. As others have mentioned, respond to the notice with proof that you qualified for Head of Household (provided more than half support, they lived with you more than half the year). The IRS will recalculate your taxes based on the correct filing status.

Where exactly is this override option? I'm staring at the error screen right now and don't see anything like that. Is it only in certain versions of TurboTax?

It's not always obvious - look for small text links near the bottom of the error message that say something like "I want to continue anyway" or "Override this warning." Sometimes you have to click on "Why am I seeing this?" first, and then the override option appears. If you're using the downloadable version, it might be under "Tools" → "Options" → "Error checking" where you can adjust the sensitivity level. For the online version, sometimes you need to click on a "More options" or "What should I do?" link that expands additional choices.

This!! I had the same issue. Check if you accidentally entered a 1099 or W-2 twice in the state section. TurboTax's interface makes this so easy to do by accident.

This is actually really helpful - I had no idea about the quarterly thing. How do I figure out how much to pay each quarter if my income isn't consistent? My construction projects vary a lot month to month.

You have a couple of options for calculating your estimated payments. The safest method is paying 100% of your previous year's tax (or 110% if your income was over $150,000). This gives you a "safe harbor" from penalties even if you end up owing more. If your income fluctuates, you can use the "annualized income installment method" using Form 2210. This lets you make payments based on what you actually earned in each period rather than 25% each quarter. Most construction businesses have seasonal fluctuations, so this might work better for you. A good tax software or accountant can help you run these calculations.

Completely agree - especially for construction. My brother's construction company got hammered in an audit because they hadn't structured things correctly. Not worth the risk when you're dealing with this kind of money. A good tax attorney will save you way more than they cost.

How long does Currently Not Collectible status typically last? Will interest and penalties continue to add up during that time?

Currently Not Collectible status doesn't have a fixed duration - it lasts until your financial situation improves. The IRS will periodically review your case, typically every 1-2 years, to see if your income has increased enough to resume payments. Some people remain in CNC status for many years if their financial hardship continues. Yes, unfortunately, interest and penalties do continue to accrue while you're in CNC status. The debt isn't forgiven - collection activity is just paused. However, there's an important benefit: the 10-year statute of limitations on collecting the tax debt continues to run during this time. So if your boyfriend's financial situation doesn't improve significantly for several years, some or all of the debt might expire before the IRS can collect it.

This is really good advice. The IRS takes worker misclassification seriously. I had a "contractor" job years ago where I was clearly an employee - set hours, company equipment, direct supervision. Filed SS-8 and got about half my tax bill wiped out!

Do you need to track every single trip? Like what if I sometimes stop at the office supply store on my way home from something else? That seems like a lot of record keeping.

You should track every business trip to maximize your deduction and protect yourself in case of an audit. For mixed-purpose trips like stopping at an office supply store on your way home, you can deduct the extra mileage if the stop was necessary for business. Apps like MileIQ or Everlance make tracking much easier - they run in the background on your phone and let you swipe trips as business or personal. The few seconds it takes to log each trip can save you hundreds or thousands in deductions. I learned this the hard way after missing out on substantial deductions my first year because my records weren't detailed enough.

I've used it for about 2 years for my consulting business. The automatic transaction categorization and receipt scanning saves me tons of time. The mileage tracker alone is worth it. And it makes tax time way less stressful - it generates reports for Schedule C that you can just hand to your accountant or transfer to TurboTax. Definitely worth the cost for the headaches it prevents.