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Ask the community...

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Amina Diop

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One thing to consider is taking out a loan to pay the taxes if the interest rate would be lower than IRS penalties. I had a similar issue (owed about $18k) and took out a personal loan at 8.9% to pay it off, which was better than the combined IRS penalties and interest. Credit unions sometimes offer decent rates for this kind of thing, or you might qualify for a 0% intro APR credit card that could buy you 12-15 months to sort things out.

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Wouldn't a HELOC be even better if they own a home? The rates are usually much lower than personal loans.

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Amina Diop

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Yes, a HELOC would definitely be better if you own a home with sufficient equity. The rates are typically much lower than personal loans, often in the 4-6% range currently. Plus the interest might be tax-deductible if you use it for home improvements (though not for paying taxes). I suggested a personal loan because many traders who get caught in this situation are younger and might not own property yet. But you're absolutely right that a HELOC is a better option if available.

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Has anyone mentioned Form 9465? That's the Installment Agreement Request. You can setup a plan for up to 72 months.

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Form 9465 is exactly what I used when I owed $15k a few years back. Super straightforward. Just know that if you owe over $10k they'll probably file a tax lien which can affect your credit.

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Can anyone check if my Forms 8606 and 5327 for 2023 are correctly filled out for my 2022 Roth IRA recharacterization?

I've been pulling my hair out trying to get this situation entered correctly into tax software, and I'm hoping someone can check if I did it right. **The Situation** In 2022, my income unexpectedly went over the Roth IRA limit. So in January 2023, I had to recharacterize about $390 of my Roth contribution and basically do a backdoor Roth conversion. Got some great advice here last year! Then in 2023, I did a standard backdoor Roth conversion of $8,500 (no gains before conversion). Now for my 2023 taxes, I have two 1099-Rs from my Roth provider: - 1099-R #1: $9,058.00 - 1099-R #2: $390.00 - Total: $9,448.00 **2022 Form 5329** - Line 24 (Total excess contributions): $390 - Line 25 (Additional tax): $23 **2022 Form 8606** - Line 16 (net converted from traditional IRAs to Roth IRAs): $390 - Line 17 (basis in amount on line 16): $390 - Line 18 (Taxable amount): $0 **2023 Form 5329** - Line 22 (Prior year excess contributions): $390 - Line 24 (Total excess contributions): $390 - Line 25 (Additional tax): $23 **2023 Form 8606** - Line 16 (amount converted from traditional IRAs to Roths): $9,448 - Line 17 (basis in amount on line 16): $9,448 - Line 18 (Taxable amount): $0 - Line 25c (Taxable amount to include on Form 1040): $0 I'm confused about the $9,058 1099-R, but I think the math is: 1. Amount recharacterized from 2022: $390 2. Amount from standard backdoor conversion in 2023: $8,500 3. And line 25 ($23) of my 2023 Form 5329 is the additional tax from 2022. I had to do some weird workarounds in both cash app and TurboTax, but I think this is correct? Also, why am I paying this $23 tax again? Do I need to take additional steps with my Roth to finally close this out?

Maya Diaz

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One thing nobody's mentioned yet - if you contributed to a Roth when you were over the income limit, you probably also need to account for any earnings on that excess contribution. The 6% penalty applies to both the excess contribution AND its earnings. Did your custodian provide a breakdown of how much of that recharacterized amount was principal vs. earnings? This might explain why your numbers don't perfectly align.

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My custodian did break it down - there were about $78 in earnings on the excess amount. Does that change how I should handle the forms? So confused about why I'm still paying penalties even after doing what I thought was the right thing.

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Maya Diaz

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That explains it! When you recharacterize, both the contribution and earnings get moved. But for the 6% penalty calculation, you're still considered to have made an excess contribution until you properly "use up" that contribution amount. You need to either: 1) reduce your 2024 Roth contribution by the $390 excess amount, or 2) remove the $390 from your retirement accounts entirely. The earnings situation is properly handled through the recharacterization, but the "slot" of contribution is what's creating the ongoing penalty. Form 5329 has a specific line where you can claim a "credit" for addressing the prior year's excess. Make sure to complete that for 2024 once you've taken one of these steps, and you'll stop the penalty cycle.

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Tami Morgan

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Question for people who've dealt with this: Does tax software automatically handle these forms correctly or do we need to manually override things? I'm using H&R Block software and it seems confused by my recharacterization.

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Rami Samuels

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In my experience, NO tax software handles Roth recharacterizations correctly, especially when they span multiple tax years. I had to manually override several fields in TurboTax last year. The biggest issue is that the tax software interview questions don't properly distinguish between recharacterization vs conversion, and they don't track your basis correctly across tax years. I'd strongly recommend either getting professional help or at minimum running your completed forms by a tool that specializes in these situations before filing.

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Tami Morgan

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Thank you! That's really helpful. I think I'll have to do some manual overrides then. I was worried I was doing something wrong but it sounds like the software itself just doesn't handle these complex situations well.

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Why were my 2022-2023 taxes so much worse as a self-employed person?

I need some genuine insight here about my tax situation. Had a conversation with friends recently about why my taxes were so much higher in 2022 and 2023, but everyone just started blaming political figures instead of giving real answers. I'm trying to understand what actually happened from a tax perspective. I've been self-employed since 2009 and have consistently increased my profits each year. Up until 2022-2023, I never had issues covering my quarterly estimated payments - I'd just write the checks without even checking my balance because I knew the money would be there. But these last two tax years hit me HARD. For the first time since starting my business, I didn't have enough in my business checking to comfortably cover both my year-end payment and 1st quarterly payment. What's weird is I'm doing roughly the same amount of business as before, but after expenses, the money just isn't stretching as far for tax payments. I'm in the process of switching to an S-Corp structure which I think will help, but I'm curious if others experienced similar issues in 2022-2023. I've talked to other self-employed friends, including a developer who said he was completely shocked by his 2023 tax bill and thought his accountant made a mistake. But it's hard to separate legitimate tax concerns from political opinions. I'm not looking to blame any political party or candidate - just trying to understand if this is a common experience for self-employed people at my income level during those specific years or if there were actual tax changes that caused this spike. Can anyone point me to legitimate information about what might have happened?

One major factor I haven't seen mentioned yet is the inflation adjustment to tax brackets. In 2022-2023, inflation was running hot, but the IRS bracket adjustments are based on earlier data. So even though your nominal income went up, your real purchasing power might not have increased proportionally. This phenomenon is called "bracket creep" and it can definitely make your tax bill feel higher even when tax laws haven't changed. Also, if you received any forgiveness of PPP loans in earlier years, that created an artificially lower tax situation that has now normalized, making the current tax environment feel more painful by comparison.

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Can you explain bracket creep more simply? I kinda get it but not really. Does this mean we should expect the same thing to happen for 2024 taxes?

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Bracket creep happens when inflation pushes your income into higher tax brackets, even though your actual purchasing power hasn't increased. For example, if you made $100,000 in 2021 and $108,000 in 2022 (an 8% increase), you might think you're 8% richer. But if inflation was also 8%, your real purchasing power stayed the same - yet you might be paying taxes at a higher rate because you crossed into a higher bracket. For 2024, the brackets were adjusted by 7.1% for inflation, which is pretty substantial. This should help reduce bracket creep compared to 2022-2023. However, if your income grows faster than that adjustment, you could still experience some bracket creep effect. The key is to look at your effective tax rate (total tax divided by total income) rather than just the dollar amount to see if you're truly paying a higher percentage.

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Sayid Hassan

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Has anyone else noticed that the cost of health insurance premiums for self-employed people went way up in 2022 and 2023? That might also be contributing to the cash flow crunch. I know my premiums went up about 23% over those two years, which ate into my available funds even though it's technically deductible.

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Rachel Tao

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Absolutely this! My health insurance premiums jumped by almost 30% between 2021 and 2023. And while yes, we can deduct them, that deduction only helps on income tax, not self-employment tax. So we're still paying 15.3% SE tax on money that immediately goes out the door to health insurance.

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I'm a bookkeeper for several small businesses, and I see this 1099-NEC issue from the other side all the time. Sometimes the error happens because the accounting software counts all invoices created during the year, not just the ones that were paid. Another possibility: did you have any expenses that the client reimbursed you for? Some clients incorrectly include expense reimbursements in 1099 totals, which they shouldn't if those were legitimate business expense reimbursements. I'd suggest checking your invoices against the client's records. It might be that they're counting an invoice you sent in December that didn't actually get paid until January 2025, which would belong on next year's 1099.

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OMG you might be onto something with the reimbursements! I did have about $1,500 in travel expenses that they reimbursed me for when I had to fly to their headquarters for a big project. I didn't count those as income in my records because they were just covering my costs. Is that what's causing the discrepancy?

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That's almost certainly the issue then! The $1,500 in reimbursed expenses plus your $7,830 in actual income equals $9,330, which is very close to the $9,450 they reported (the remaining $120 difference could be a calculation error or another small reimbursement you're forgetting). Reimbursed expenses should NOT be included on your 1099-NEC if they were legitimate business expenses. The client should issue a corrected 1099-NEC showing only the $7,830 in actual service income. If they included the reimbursements, they're reporting it incorrectly. Take this explanation to your client and specifically point out that expense reimbursements shouldn't be on the 1099-NEC. Many small businesses don't realize this and their accountants might not catch it if they're just given total payment figures.

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Question about this situation - I have the opposite problem. My client UNDER-reported on my 1099-NEC by about $2,000. Should I just report my actual higher income on my Schedule C and not worry about getting a corrected 1099? Seems like paying more tax than the 1099 shows wouldn't trigger any IRS concerns?

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You're right that reporting MORE income than what's on your 1099-NEC won't trigger IRS concerns - they're generally more worried about underreporting. However, for your own protection and record-keeping, it's still best to request a corrected 1099-NEC that accurately reflects what you were paid. The reason is that your client is likely taking a tax deduction for what they paid you. If their records show they paid you $2,000 more than what they reported on your 1099-NEC, that discrepancy could potentially cause problems for them in an audit, which could circle back to questions about your income.

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Thanks for the advice! I'll reach out to them and request a corrected form. They've been pretty disorganized with their accounting (they're a startup) so I'm not surprised there was an error. Better to get everything aligned properly.

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Ravi Kapoor

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Something similar happened to me in 2023. Here's the form you need that nobody tells you about: Form 3911 "Taxpayer Statement Regarding Refund." This officially alerts the IRS that your refund is missing and starts a trace. You can download it from the IRS website. Also try contacting your local Taxpayer Advocate Service office - they can sometimes work miracles when normal channels fail.

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Amina Diop

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Thank you for mentioning Form 3911! Is there a waiting period before I should file this, or can I submit it now since it's been over 3 months since I mailed my return?

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Ravi Kapoor

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You can file Form 3911 now since it's been more than 8 weeks since you mailed your return. The IRS recomm

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Freya Larsen

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Just wondering if you filed an extension just in case? Even though you sent your return, if they truly lost it and you have no proof of mailing it (like certified mail), the IRS could potentially hit you with late filing penalties. Might be worth filing Form 4868 for an extension if you haven't already, just to cover yourself.

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This is actually bad advice. Filing an extension now would be pointless since we're past the original filing deadline. Extensions have to be filed BEFORE the due date. At this point OP needs to focus on getting the original return processed or filing a duplicate.

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