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Ask the community...

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Yara Nassar

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Just wanted to add that CashApp Tax actually handles 1099-Rs pretty well in my experience. I had several last year - some taxable, some not. Make sure you carefully select the correct type of account (Roth IRA in your case) when entering each form. The software will then guide you through the process. One thing to watch for: if you enter the gross distribution in Box 1 but Box 2a is blank (which happens with non-taxable Roth distributions), CashApp Tax might ask you to confirm that the taxable amount is zero. Don't skip this step! Confirming the zero taxable amount ensures your tax-free distributions are reported correctly.

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Dylan Hughes

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Thanks for the tip about confirming the zero amount! I just started entering my forms and noticed CashApp Tax did ask me about this. So that's normal then? And one more thing - should I be concerned about any penalties on the newer account since I'm 42 and took money out of a retirement account?

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Yara Nassar

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Yes, that confirmation step is completely normal! CashApp Tax is double-checking that you're telling it the distribution is non-taxable, which is correct for qualified Roth distributions. Regarding the newer account, since you're under 59½, you might face a 10% early withdrawal penalty on the earnings portion (but not on your contributions). However, there are exceptions to this penalty - like using the money for a first-time home purchase, certain education expenses, or if you have unreimbursed medical expenses exceeding a certain percentage of your income. The distribution code in Box 7 (you mentioned code J) suggests it's an early distribution, so CashApp Tax should calculate any applicable penalties automatically when you enter the form correctly. If you're eligible for an exception, make sure to indicate that when prompted by the software.

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StarGazer101

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I switched from TurboTax to CashApp Tax this year and had to enter multiple 1099-Rs too. One thing that tripped me up was Box 7 distribution codes - make SURE you enter these exactly as they appear on your form. I accidentally selected the wrong code initially and it completely changed my tax calculation. Also, did your 1099-Rs have anything checked in Box 2b? That "Taxable amount not determined" box can affect how the software handles the entry.

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This is such a good point! I made the exact same mistake last year with distribution codes and ended up having to file an amended return because it showed my qualified Roth distribution as taxable when it shouldn't have been. Those tiny codes make a huge difference in the tax treatment.

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3 Don't want to complicate things further, but don

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17 Which states actually have these lower estate tax thresholds? Is there a simple list somewhere? My parents have property in multiple states and I'm trying to figure out if this is something we need to worry about.

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3 As of 2023, the states with estate taxes are: Connecticut, Hawaii, Illinois, Maine, Maryland, Massachusetts, Minnesota, New York, Oregon, Rhode Island, Vermont, Washington, and the District of Columbia. The exemption thresholds range from around $1 million (Massachusetts, Oregon) to $9.1 million (Connecticut). Some states also have inheritance taxes, which are different - they're based on who receives the assets rather than the total estate value. Those states are Iowa, Kentucky, Maryland, Nebraska, New Jersey, and Pennsylvania. Maryland actually has both types of taxes! If your parents have property in multiple states, you definitely need to look into each state's rules. The concept of "domicile" becomes really important in determining which state's laws apply.

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14 Question for anyone who knows: If I'm the executor of an estate AND a beneficiary of an IRA, am I personally liable if I distribute the IRA to myself (as the beneficiary) before paying the estate taxes? This is keeping me up at night.

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8 Yes, you would be personally liable in two ways. First, as the executor, you have a fiduciary duty to handle the estate properly, which includes paying taxes before distributions. Second, as a beneficiary receiving assets from a taxable estate, you have transferee liability for your proportionate share of estate taxes. The IRS can come after you both as the executor who failed to ensure taxes were paid and as the beneficiary who received assets that should have been used to pay taxes. I strongly recommend getting professional help with this situation to avoid serious personal liability.

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Ethan Scott

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Just want to add something important about Head of Household that nobody mentioned yet. If your sister is still claiming your niece as a dependent, you should make sure she actually legally CAN claim her. The IRS has a "residency test" for claiming a qualifying child - generally, the child must live with the parent/guardian for more than half the year. If your niece lives with you full-time for 9+ months, your sister technically might not be eligible to claim her anymore. The IRS would consider you to have the stronger claim since the child lives with you. This isn't just about who "gets" to claim the dependent - filing incorrectly could trigger audits for both of you.

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That's a really good point I hadn't considered. So you're saying that based on the residency test, my sister might not actually be eligible to claim my niece anymore since she's been living with me for most of the year? I definitely don't want either of us to get audited. Do you know if there's any exception to this residency test? Like if there's some kind of temporary arrangement or something? We didn't really think about the tax implications when my niece came to stay with me.

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Ethan Scott

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Yes, that's exactly what I'm saying. The residency test is pretty clear - a qualifying child must live with the taxpayer for more than half the year. With your niece living with you for 9+ months, your sister likely doesn't meet this requirement anymore. There are some exceptions to the residency test, but they're limited to specific situations like temporary absences (medical care, education, vacation, etc.), children of divorced or separated parents with a formal agreement, or kidnapped children. From what you've described, it doesn't sound like any of these exceptions would apply in your situation. I'd recommend having an honest conversation with your sister about the tax situation. The IRS would consider you to have the stronger claim to be the qualifying taxpayer for your niece based on the residency test.

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Lola Perez

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I went through this EXACT situation with my younger brother! Here's what I learned: For Head of Household, you need: 1) Be unmarried on Dec 31 2) Pay more than half of keeping up your home 3) Have a qualifying person live with you more than half the year The key is that "qualifying person" part. Since ur sister still claims your niece as a dependent, you can't use her to qualify for HOH. Its not just about who lives with who, but who can legally claim who as a dependent. My advice: talk to ur sister. If the kid lives with you full time, YOU should probably be the one claiming her as a dependent, not your sister. Then you'd qualify for HOH plus child tax credits. Would make more sense tax-wise given the actual living arrangement.

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This is the right answer! The residency test is super important for determining who can claim a dependent. If the niece lives with OP for most of the year, the sister technically shouldn't be claiming her unless there's a special exception. In my experience, the tax benefits for the person who has the child living with them (HOH status + child tax credits) are usually much better than just claiming a dependent who doesn't live with you. Might be worth both sisters calculating their taxes both ways to see what makes the most financial sense for the family as a whole.

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Juan Moreno

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Something nobody's mentioned yet - if you're renting the garage to your own business, you need to be careful about the rental amount. The IRS will look for fair market value, especially in related party transactions. If you charge your business significantly above market rate for the garage space, that could trigger scrutiny regardless of the Augusta Rule situation. Have you considered having the business purchase the garage outright through a partial property sale? That might be cleaner from a tax perspective, though it comes with its own complications regarding property division.

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Justin Trejo

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That's a really good point about the fair market value. I've been researching comparable workshop spaces in my area to make sure I'm charging a reasonable amount. Would you recommend getting some kind of formal appraisal to document the fair market rental value? I hadn't considered selling the garage space to the business - that seems complicated since it's on the same property lot. Wouldn't that create zoning issues or require subdividing the property?

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Juan Moreno

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A formal appraisal would be ideal for documentation, but even gathering 3-5 comparable rental listings from your area can serve as reasonable support for your rental rate. Save screenshots or printouts of similar workspace rentals to keep with your tax records. You're absolutely right about the complications with selling just the garage. Unless your property is already zoned for mixed use, you'd likely face zoning issues. Subdividing residential property to sell a portion to a business entity is possible but extremely complex and might trigger reassessment of property taxes or other consequences. The rental approach you're considering is likely simpler from a practical standpoint.

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Amy Fleming

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Quick question - would converting the garage into legal living space (adding bathroom, kitchen, etc.) change this situation at all? I'm in a similar spot but was thinking of making my garage into an ADU that I could rent to my business partners when they visit for quarterly meetings.

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Alice Pierce

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If you convert it to a legal ADU with living facilities, it would likely be considered a separate dwelling unit entirely. This could actually work in your favor for the Augusta Rule because each dwelling unit gets its own 14-day exemption. Just make sure the conversion is permitted and up to code, otherwise you could have issues with both the IRS and local authorities.

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Are you sure you didn't receive a 1099-K as well from Uber? Starting in 2022, many states required platforms to issue 1099-Ks for earnings over $600 (instead of the old $20k threshold). The 1099-NEC might just be showing bonuses or incentives, while the bulk of your driving earnings could be on a separate 1099-K or in your yearly tax summary. Check your Uber driver dashboard under "Tax Information" - there should be a complete tax summary there that will clarify what's what. My partner drives for Uber and had a similar confusion last year.

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GalaxyGazer

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You might be right! I just checked my email spam folder and found another message from Uber with a tax summary PDF. It shows the full $4000+ broken down as: customer payments, Uber fees, and then the promotions (which match the $600 on the 1099-NEC). So it sounds like I was supposed to report all of it, but the 1099-NEC only covers a small portion?

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That's exactly it! The tax summary shows your complete picture. The customer payments minus Uber's fees is your actual service income that needs to be reported on Schedule C. The promotions on the 1099-NEC are also income but are being reported separately by Uber. So on your amended return, you'll need to make sure you're reporting the full amount from the tax summary, but be careful not to double-count the promotion amount that's on both the tax summary and the 1099-NEC. You're actually not that far off in what you filed if you reported the full $4000+ already - you just need to make sure it's allocated correctly on your Schedule C.

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Omar Hassan

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Wait, I'm confused about something. If the OP reported MORE income than was on the 1099 ($3000+ vs $600), wouldn't that mean they OVERPAID their taxes? Why would the IRS come after them for an audit when they paid more tax than required?

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The issue isn't necessarily about paying too little tax, but about information not matching up. When your reported income doesn't match what the IRS gets from third parties (like Uber), it raises flags in their system regardless of which direction the discrepancy goes. The IRS automated systems look for matches, not just underpayments.

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