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I went through bankruptcy with about $500k in IRS debt last year. Few things to keep in mind: 1) Make sure you file all required returns before bankruptcy. Any unfiled returns will definitely not be dischargeable. 2) Be careful about any transfers of assets in the years leading up to bankruptcy - the court looks back several years and can claw back anything they consider inappropriate. 3) Document EVERYTHING about your current financial situation very thoroughly. The courts are more skeptical when large tax debts are involved. 4) The IRS will scrutinize your case much more closely than a typical bankruptcy. They may send their own attorneys to challenge the discharge of tax debt. 5) Your trading accounts and history will be examined closely. Be prepared to explain any large withdrawals. Good luck! It's a stressful process but there is light at the end of the tunnel.
Thanks for sharing your experience! How long did the whole process take from filing to discharge? And if you don't mind sharing, were you able to get all of your tax debt discharged or just a portion?
The entire process took about 9 months from filing to discharge, which is longer than typical bankruptcies. The tax components definitely slow things down because the IRS reviews everything carefully. I was able to get about 80% of my tax debt discharged. The remaining 20% wasn't dischargeable because those taxes were from a year where I filed late and hadn't yet hit the 2-year mark from filing date. I ended up on a payment plan for that portion, but having 80% wiped out made that manageable.
Don't overlook the emotional toll this will take. Bankruptcy with the IRS involved is WAY more stressful than regular bankruptcy. I went thru this in 2022 and spent almost every night unable to sleep. Get some support - therapist, support group, whatever. The stress can be unbearable especially when ur young and feel like ur life is ruined. Also prepare for after bankruptcy. Trading might be harder without capital. Have a backup plan for income. The discharge feels amazing but then reality hits that you need to rebuild completely.
This is so true. I went through tax bankruptcy last year and the emotional side was the hardest part. Did you find that lenders were especially harsh because it was tax debt rather than credit cards or medical bills? I've been struggling to rebuild my credit because it seems like lenders see tax bankruptcy as a bigger red flag.
A big thing you need to figure out is your cost basis. Since you inherited the stock, your basis should be the fair market value on the date of death (or alternate valuation date if the executor chose that). This is called a "stepped-up basis." For a large inheritance like that, there should be estate documents that show the valuation. Make sure you have those before filing, because using the wrong basis could cost you thousands in deductions.
What happens if you can't find documentation of the exact value on date of death? My dad left me some stocks but passed away during COVID and everything's a mess with paperwork.
If you can't find the documentation, you can try to reconstruct it. You'll need to determine the date of death and then research what the stock was trading for on that day - most financial websites have historical price data. Get the closing price on that date and multiply by the number of shares. If it was a significant inheritance, the estate may have filed an estate tax return (Form 706) which would have the valuation. You can request a copy from the IRS with Form 4506. Another option is to contact the broker who handled the account - they often have historical valuations on record.
Everyone is talking about tax benefits, but has anyone considered that some of these failed bank stocks might actually recover some value? After Washington Mutual collapsed in 2008, the worthless stock (WAMUQ) actually traded up to about 50 cents from nearly zero as speculators bet on leftover assets.
As a former IRS employee, I strongly recommend looking into the Taxpayer Advocate Service as mentioned above. But also consider calling the direct number for the auditor assigned to your case (should be on your audit letter). They can often work with you directly if you're upfront about your situation. Also, you might qualify for audit reconsideration if you have new information or documentation that wasn't previously considered. This can be done without representation. The key is staying organized and responding to all IRS communications promptly. Many audits get worse simply because people avoid dealing with them out of fear.
Thanks for the insider perspective! My audit letter does have a specific person's name and number. I've tried calling a few times but always get voicemail. Is it better to keep trying that direct line or go through the main IRS number?
Definitely keep trying the direct line to your assigned auditor. Leave detailed but brief voicemails with your name, tax ID number (last 4 digits only for security), and the best time to reach you. Most auditors handle multiple cases and check messages regularly, even if they don't answer calls immediately. The main IRS line will just put you in the general queue and whoever answers likely won't have immediate access to your specific case details. Your assigned auditor already knows your file and has the authority to make decisions on your case. Persistence is key - try calling at different times of the day, especially early morning right when offices open.
I went through an audit last year and found that my local H&R Block office offered audit representation services for about $850, which was way less than what tax relief companies quoted me. Also check with any tax preparer who may have done your original return - they sometimes include audit protection for returns they prepared, even from previous years.
Don't forget about HSA contributions if you have a high-deductible health plan! This is often overlooked but is one of the best AGI reducers available. For 2023, you can contribute up to $3,850 (self-only) or $7,750 (family), plus an extra $1,000 if you're 55+. The great thing is you can still make 2023 contributions until April 15, 2024. It's triple tax-advantaged: reduces your AGI now, grows tax-free, and withdrawals for medical expenses are tax-free. Even if you didn't have an HSA-eligible plan all year, you can prorate your contribution based on how many months you were eligible.
If I open an HSA account now in 2024, can I still make a contribution that counts for 2023? My employer offered a high-deductible plan that I was enrolled in all of 2023, but I never set up the HSA. Would really help if I could still get that AGI reduction.
Yes, you absolutely can! As long as you were enrolled in a qualified high-deductible health plan (HDHP) during 2023, you can open an HSA now and make contributions for the 2023 tax year until the tax filing deadline (April 15, 2024). Since you were enrolled in the HDHP for the entire year, you can contribute the full amount - $3,850 for individual coverage or $7,750 for family coverage. Just make sure to designate it as a 2023 contribution when you make it. This will reduce your 2023 AGI by the full contribution amount. It's one of the few retroactive tax moves you can still make this year to affect last year's taxes.
Has anyone used the qualified business income deduction (Section 199A) to reduce their AGI? I have a small side business that made about $12k last year but I'm confused if this counts as an AGI reducer or if it comes after AGI is calculated.
The Qualified Business Income Deduction (Section 199A) is a bit confusing position-wise. Technically, it doesn't reduce your AGI - it's actually taken after your AGI is calculated but before your taxable income is determined. It's similar to the standard or itemized deduction in that regard. So while it's an amazing deduction that can reduce your taxable income by up to 20% of your qualified business income, it unfortunately won't help lower your AGI for things that are AGI-dependent. Focus instead on retirement contributions, HSA, and other above-the-line deductions to reduce your actual AGI.
Aiden Chen
Something nobody's mentioned yet - make sure your mom doesn't claim herself as independent on her own tax return if she files one for her part-time job. You'll both get flagged if she claims herself and you also claim her as a dependent.
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Zoey Bianchi
ā¢This! My brother and I got audited because my mom filed her own taxes claiming herself while my brother also claimed her. What a nightmare that was to sort out.
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Christopher Morgan
One other thing I learned when claiming my parent - if your mom has medical expenses that you pay, you can include those when you itemize deductions on your return. Helped me get above the standard deduction threshold last year and saved some money.
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