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This might sound obvious, but have you tried using the "Where's My Refund" tool on the IRS website specifically for your 2022 return? My sister had a similar issue and it turned out her 2022 return needed additional verification, but she never received the letter they supposedly sent. Also check if your address changed between 2022 and 2023 - sometimes correspondence gets lost if you moved and the IRS is still using your old address.

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NightOwl42

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Yes, I've been checking "Where's My Refund" for months for my 2022 return. It just says "Your tax return is still being processed" with no other information. I did move in late 2022, but I updated my address with USPS. Do I need to update my address directly with the IRS too?

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Yes, you absolutely need to update your address directly with the IRS. The USPS mail forwarding doesn't automatically notify the IRS of your new address. This could definitely explain why you might have missed important letters about your 2022 return! You can update your address with the IRS by submitting Form 8822 (Change of Address). In the meantime, I'd recommend using one of the methods others suggested to contact the IRS directly about your 2022 return - especially now that we know you moved, there's a good chance they've been sending verification requests or other important notices to your old address.

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Paolo Romano

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Has anyone actually received a 2022 refund after filing their 2023 taxes? I'm in the exact same boat - still waiting on 2022 money while my 2023 return is already accepted. Getting really worried the IRS will just "forget" about the older refund.

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Amina Diop

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Yes! I received my very delayed 2022 refund about 3 weeks after filing my 2023 taxes. The two systems operate independently so one doesn't affect the other. My 2022 return had some issues with education credits that needed manual review, but they eventually sorted it out without me having to call.

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Val Rossi

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Just to add another perspective - I've been a delivery subcontractor for 5 years now. You definitely want to track EVERYTHING. Beyond just gas, make sure you're deducting: 1. Any portion of insurance you pay 2. Parking and tolls (like mentioned above) 3. Car washes (if you pay for them) 4. Any required safety equipment or uniforms 5. Your cell phone percentage used for work 6. Meals during long shifts (50% deductible) My accountant catches stuff I would never think about. The actual expense method can actually work out better than mileage sometimes depending on your situation.

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Eve Freeman

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Isn't there a risk of getting audited if you claim too many expenses? I'm a new subcontractor and nervous about deducting too much.

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Val Rossi

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There's always a small audit risk with any business deductions, but it's not about claiming "too many" expenses - it's about claiming legitimate business expenses and having proper documentation. Keep good records of everything - receipts, logs, payment statements. The IRS understands that businesses have expenses. As long as they're legitimate and you can back them up if questioned, you shouldn't be worried. It's your right to take all legal deductions you're entitled to! Just don't make things up or inflate numbers, and you'll be fine.

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Quick question - does anyone use any specific apps to track their expenses as a subcontractor? I'm doing delivery work too and trying to stay organized for next year's taxes.

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Caden Turner

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I've been using Stride for the past couple years. It's free and lets you track mileage with GPS plus all your other expenses. You can take photos of receipts right in the app. Really helpful at tax time because you can categorize everything properly for Schedule C.

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Olivia Clark

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Just to add some additional info here - if you have ANY earned income from early 2023 before your disability prevented you from working, that counts toward the $2,500 threshold. Some people forget about jobs they had just for a month or two at the beginning of the year. Also, if your disability is approved retroactively and you get a lump sum payment later, that won't help for the earned income requirement, but you'll want to file Form 915 to potentially exclude some of that lump sum from taxation in the year you receive it.

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Thanks for mentioning this! I actually did work in January 2023 very briefly before my condition worsened, but it was only about $1,200 in earnings. Is there any way that partial amount would help me qualify even though it's below the $2,500 threshold?

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Olivia Clark

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That $1,200 in earnings would count toward the $2,500 threshold, but unfortunately you'd still be short of the minimum needed to qualify for the refundable portion of the Child Tax Credit. You'd need to reach at least $2,500 in earned income to start qualifying. However, it's still important to file a tax return showing this income, especially if you had any withholdings that might be refundable. Plus, having filed returns consistently will help when your disability is approved, as it creates a clearer picture of your work history and the onset of your inability to work.

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Also consider looking into whether you might qualify for the Credit for Other Dependents, which is a non-refundable credit of up to $500 per dependent who doesn't qualify for the Child Tax Credit. Even without income, establishing a filing history can be important for future benefits.

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This is actually not great advice for someone with zero income. Non-refundable credits can only reduce tax liability, and with no income there's no tax liability to reduce. So the Credit for Other Dependents wouldn't help in this specific situation.

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As someone who works in tax resolution, here's my advice: Get your IRS transcripts first. You can request them online at IRS.gov or by filing Form 4506-T. This will show what information the IRS has about your income for those years. For the Boston area, try contacting the Boston Tax Help Coalition - they provide free tax preparation for low to moderate income taxpayers and might be able to help with your situation or at least point you in the right direction.

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Does it matter if some of the unfiled years included illegal income? Not asking for a friend...seriously wondering how that affects the process.

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Regarding income from illegal activities, it technically should be reported on tax returns (yes, seriously - the IRS requires reporting of all income regardless of source). However, in practice, most people in this situation report it as "other income" without specifying the source. The Fifth Amendment can protect you from having to disclose the specific illegal source, but not from paying taxes on the income itself. That said, this is definitely an area where having professional representation is crucial - ideally an attorney with tax expertise who can maintain attorney-client privilege.

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Has anyone used the IRS Fresh Start Program? I heard it helps with penalties but not sure if it applies to cases with this many unfiled years?

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LongPeri

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I used it after being behind 7 years. It helped me avoid some penalties, but you have to file all required returns first before you can access most of the benefits. The installment agreements were surprisingly reasonable tho.

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Structuring the Acquisition of an Agent's Business with Debt Owed to Our Company

Our company is preparing a proposal to acquire an agent's struggling commission-based business (essentially their book of business). The agent currently owes our company approximately $750,000, and we're trying to find the optimal way to structure this transaction. We want to remove this accounts receivable from our books without recording it as bad debt, while also avoiding hitting the agent with a massive cancellation of debt (COD) income tax bill. What's the most efficient way to structure the purchase of this business in exchange for the value of the debt they currently owe us? I've considered several approaches: 1. Extending a loan to the agent for the $750k, having them pay down the original debt, then buying their business for a nominal amount ($1). We could establish a 10-year payment plan for the new loan, or create an earnout structure that gradually eliminates the debt if certain business targets are achieved. 2. Structuring the purchase explicitly as an exchange for debt cancellation. However, this would trigger COD income for the agent. Is there a way to structure this so the debt cancellation occurs gradually over several years to spread out their tax impact? 3. A hybrid approach where we loan them money to clear the current debt, purchase the business with no down payment, but set up a payment plan that provides them money over several years which they can use to repay the loan. Our CFO and legal team just asked for my thoughts on this situation, and I'm feeling a bit out of my depth on proposing the optimal purchase structure. Any insights would be greatly appreciated!

You mentioned the agent owes about $750k. Have you considered a Section 338(h)(10) election if they're a corporation? This lets you treat a stock sale as an asset sale for tax purposes. The key benefit is you get a stepped-up basis in the assets while the seller can use losses to offset gains. We did this last year when acquiring a struggling insurance agency. Their debt to us was about $500k, and this structure worked well to minimize immediate tax impacts while getting their book of business.

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Layla Mendes

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I'm not entirely sure of their business structure, but that's definitely something I'll look into. How complicated was the paperwork for this approach? Did you need specialized legal help?

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The paperwork is definitely more complex than a straightforward asset purchase. We needed both our tax attorney and accountant involved to structure it properly. The election itself is made on Form 8023, but the agreement needs very specific language to support it. The biggest challenge was agreeing on the asset allocation with the seller since this impacts the tax consequences for both sides. We ended up allocating more value to assets that gave us better depreciation/amortization treatment while minimizing their gain recognition. It took about 6 weeks to finalize all the details, but the tax savings made it worthwhile.

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Drake

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Has anyone considered the implications if the agent files bankruptcy before completing this transaction? I nearly got burned by this exact scenario.

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Sarah Jones

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Great point. If bankruptcy is filed within 90 days of any payment or transfer, it could potentially be clawed back as a preferential transfer. I'd recommend doing a solvency analysis as part of your due diligence.

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