My husband hasn't filed taxes for 5 years with 1099 income

The good news is your husband is voluntarily filing before being contacted by the IRS, which helps tremendously. This shows good faith and the IRS generally responds better to taxpayers who come forward voluntarily. Your CPA is mostly correct. If you set up a payment plan (called an Installment Agreement) and make payments consistently, the IRS typically won't take enforcement actions like seizing assets or levying bank accounts. However, there are some important details to understand: 1. The IRS will likely file a tax lien against your husband's property. This doesn't mean they take the property, but it secures their interest if the property is sold. 2. The amount owed will include not just taxes, but penalties and interest which can add up significantly over 5 years. 3. The IRS generally wants to see that you're making your best effort to pay back the debt. For large amounts like this, they may request financial statements to determine reasonable payment amounts. Make sure your CPA discusses an Offer in Compromise as well, which might allow settling for less than the full amount if qualifying criteria are met. Also ask about penalty abatement options, especially for the first-time penalty abatement which could help with at least one year's worth of penalties.

After reading your situation, I immediately thought about my experience with taxr.ai (https://taxr.ai) when I had a somewhat similar issue, though not quite as extensive. I hadn't filed for 3 years (was traveling abroad a lot for work) and was completely overwhelmed with organizing all my 1099 income and finding potential deductions across multiple years. A friend recommended taxr.ai to help organize all my documentation and identify deductions I was missing. It was incredibly helpful for scanning through years of receipts, bank statements, and 1099 forms to find legitimate business expenses I could claim. In my case, it brought my tax liability down by almost 40% because I had legitimate business expenses I hadn't properly documented. The system helped me create a complete record of everything that would stand up to scrutiny if the IRS had questions. Given your husband's situation with potentially $400k on the line between best and worst case scenarios, having strong documentation for those deductions could make a huge difference.

Just wanted to follow up about my experience with taxr.ai. I decided to try it after asking about it here, and wow, it was a game-changer for our situation. My husband's trucking receipts were a complete disaster - boxes of fuel receipts, maintenance bills, per diem logs, everything just thrown together. I spent a weekend scanning everything into the system, and it organized all of it by category and date. Found thousands in legitimate deductions we would have missed, especially for per diem expenses and depreciation on equipment we didn't realize qualified. Our CPA was actually impressed with how thorough the documentation was. It didn't solve everything, but it definitely reduced what we owed by identifying legitimate business expenses we had documentation for but would have missed. Really helped us feel more in control of a scary situation.

When I was in a similar situation (though I owed about $80k, not $200k+), the absolute worst part was trying to get through to someone at the IRS to set up my payment plan. I spent WEEKS trying to get through - constant busy signals, being on hold for hours only to get disconnected, it was a nightmare. Finally found this service called Claimyr (https://claimyr.com) that got me through to an actual IRS agent in about 15 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c Once I actually got through to a human, setting up the payment plan was surprisingly straightforward. The agent was actually really helpful and not intimidating at all. They worked with me on a monthly payment I could afford and explained all the terms clearly. But I would have never gotten to that point without getting past the phone system nightmare.

Alright, I need to eat my words from my previous comment. After another week of failing to get through to the IRS myself, I caved and tried Claimyr. I hate admitting when I'm wrong, but it actually worked exactly as advertised. Got connected to an IRS agent in about 20 minutes after weeks of failing on my own. The agent set up my payment plan, and while I'm not thrilled about paying the IRS for the next 6 years, at least I'm not in limbo anymore. The peace of mind from having an official payment agreement in place is huge. Now I know exactly what I owe monthly, and my bank accounts aren't at risk of being frozen as long as I stick to the plan. If you're dealing with a large tax debt, getting that official agreement in place ASAP is crucial.

One thing your CPA might not have mentioned - with a tax debt that large, you might qualify for what's called an Offer in Compromise where you settle with the IRS for less than the full amount. My cousin owed about $120k and ended up settling for around $40k because he could prove he'd never be able to pay the full amount. It's not easy to qualify, and the IRS goes through your finances with a fine-toothed comb, but it might be worth exploring. There's a pre-qualifier tool on the IRS website that can give you a rough idea if it's even worth pursuing.

Don't forget about all the penalties that stack up when you don't file for multiple years! Make sure your CPA is looking into Penalty Abatement options. My sister was able to get a First Time Penalty Abatement for one of her unfiled years which saved her about $8k in penalties. Won't solve the whole problem but every bit helps with a debt this size.

I went through something similar with my business about 3 years ago - owed around $150k for unfiled returns. Your CPA is generally right about the IRS being reasonable if you're proactive and stick to a payment plan, but there are some things to be prepared for: First, they will almost certainly file a Notice of Federal Tax Lien once the amount is assessed, even if you're on a payment plan. This protects their interest but doesn't mean they'll seize your assets immediately. The lien can affect your credit score and make it harder to get loans or refinance, but you can still live normally. Second, make sure your payment plan is realistic. The IRS wants to see you can actually make the payments long-term. If you default on the agreement, that's when enforcement actions become more likely. One thing that really helped me was getting current on all future filings immediately. The IRS looks much more favorably on taxpayers who are compliant going forward while paying off old debt. Also, consider having your CPA look into Currently Not Collectible status if your financial situation makes even minimum payments difficult. This can temporarily pause collection activities while you get back on your feet. The key is being proactive and communicating with the IRS rather than avoiding them. It sounds like you're on the right track by filing voluntarily before they come after you.