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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.
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Dylan Baskin
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.
Lauren Wood
ā¢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.
Dylan Baskin
ā¢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.
Ellie Lopez
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.
That's actually a good point. I was holding onto some Lehman Brothers shares after they went bankrupt thinking they might bounce back, but in the end I would have been better off just taking the tax loss. The shares did briefly spike to about 20 cents though.
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Just wanted to mention that if you're only filing a few 1099-NECs, you can file them for free directly on the IRS website through the FIRE system. No need to buy forms or pay for services if you're comfortable navigating the government website.
Andre Dupont
ā¢I tried using the IRS site but got super confused. Is there a specific tutorial you followed to figure it out?
The IRS site is definitely not the most user-friendly, I'll admit. I found their tutorial in Publication 1220, but it's pretty technical. Here's what worked for me: create an account first, then go to the "Filing Information Returns Electronically" (FIRE) section. For simpler guidance, I actually ended up watching a YouTube tutorial someone made that walked through the process step by step. Just search "how to file 1099-NEC on IRS FIRE system" and you'll find several helpful videos that are much clearer than the official instructions.
Hey I went through this exact thing last month! I only had one contractor but got the 3-up form. I just filled out the top section and left the rest blank. Mailed it in and everything was fine. Don't overthink it!
ThunderBolt7
ā¢Did you also e-file with the IRS or just mail the paper form? I'm trying to figure out the easiest way.
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StarSailor}
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?
StarSailor}
ā¢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.
Miguel Silva
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.
How did that work out for you? Did they manage to reduce what you owed? I've heard mixed things about H&R Block's representation services.
Sean Doyle
Have you tried looking into tax attorneys who offer consultation services? I had a similar situation last year when I was starting a small business but wanted to handle the ongoing tax work myself. I found a tax attorney who charged me for a 2-hour consultation where I brought all my questions. She answered everything, gave me some resources to reference, and didn't try to sell me on recurring services. It wasn't cheap (about $400 for the session), but the advice saved me probably thousands in potential mistakes.
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Ravi Gupta
ā¢That's an interesting approach. Did you just search for "tax attorney consultation" or how did you find someone willing to do this?
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Sean Doyle
ā¢I actually found her through my state's bar association website. They have a referral service where you can search for attorneys by specialty and many list whether they offer consultation services. I called a few and specifically asked about a one-time paid consultation. A good approach is to be very clear upfront about what you want - I literally said "I'm looking for a one-time paid consultation to get answers to specific tax questions as I'll be handling my own filing." Some weren't interested, but others were perfectly happy with this arrangement.
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Zara Rashid
Don't overlook the free resources! I know you said you're willing to pay, but I've had great experiences with VITA (Volunteer Income Tax Assistance) volunteers. If your income is under $60k, they offer free tax help. Even if you don't qualify for their free filing help, many of the volunteers are really knowledgeable and can answer questions. The same goes for Tax-Aide from AARP - they focus on seniors but often help others too.
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Luca Romano
ā¢Can confirm this! I volunteered with VITA for 3 years and we regularly had people come in just to ask questions about their tax situation. As long as it's not during the busiest parts of tax season, most volunteers are happy to help even if you're not having them prepare your return.
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