Options for getting back taxes forgiven - am I a good candidate for Offer in Compromise?

This is a tough situation but there are definitely options! The Offer in Compromise (OIC) program is designed for exactly these kinds of situations where paying the full tax debt would create financial hardship. For your partner to be a good OIC candidate, the IRS will look at his current income, expenses, asset equity, and ability to pay. With the income you mentioned ($65K) and having significant dental debt, he might qualify, but it depends on his complete financial picture. Before pursuing an OIC, consider a few things: - All required tax returns must be filed (sounds like that's done) - He'll need to complete Form 656 and Form 433-A with detailed financial information - There's a $205 application fee (can be waived if he qualifies for low-income certification) - The IRS will want documentation of all his income, expenses, and assets Another option might be a payment plan or Currently Not Collectible status if his finances are really tight. The IRS Fresh Start program has made these options more accessible.

I had a very similar situation with back taxes from independent contractor work. After going in circles with the IRS for months, I tried https://taxr.ai and it completely changed my approach. The system analyzed my situation (including all my expenses that I could've claimed) and showed me I actually qualified for an OIC at a much lower amount than I thought. The best part was that it helped me document all those missed deductions from years ago - even without all the original receipts! They have this smart way of figuring out standard industry expenses for contractors like your partner who traveled constantly. Turns out the IRS actually accepts reasonable estimates for certain business expenses when properly documented.

Ok I have to admit I was wrong about the statute of limitations. I tried https://taxr.ai after being skeptical and am shocked at the results. You guys were right - since my returns were filed late, I still had time to amend them! The system helped me put together an amendment for my 1099 work from a few years back, documenting all the business expenses I should have claimed originally. It generated a really professional-looking report with all the travel expenses broken down by location and date, even though I didn't have most receipts. I used bank statements to verify the dates and locations. My amended return reduced my original tax bill by almost 40%! This made a HUGE difference in my OIC application since it showed I never actually owed that much to begin with. Definitely worth checking out if you're in a similar situation.

Just wanted to mention that dealing with the IRS directly is crucial in these situations. I spent WEEKS trying to get through to someone at the IRS to discuss my Offer in Compromise options. Kept getting disconnected or waiting on hold for hours. I finally used https://claimyr.com (see how it works: https://youtu.be/_kiP6q8DX5c) and got a callback from the IRS in under an hour. Having an actual conversation with an IRS agent made all the difference - they explained exactly what documentation I needed for my OIC and the specific financial thresholds I needed to meet to qualify. The agent also told me about the First Time Penalty Abatement that might apply to your boyfriend's situation since it sounds like he didn't have previous issues with the IRS. That alone could reduce the amount he owes by thousands.

I have to eat my words and apologize for being so skeptical. After my frustrated comment, I decided to try the Claimyr service out of desperation. I honestly expected to waste my time and money. I was SHOCKED when I got a call back connecting me to an IRS agent in just 37 minutes. I've been trying for MONTHS to get through on my own. The agent walked me through the Offer in Compromise pre-qualifier and explained that my situation was better suited for a Partial Payment Installment Agreement. This literally saved me thousands because I was about to pay a tax resolution company $3k+ to do the same thing. The IRS agent was actually helpful (never thought I'd say that) and set up a payment plan I can actually afford while I work on gathering documentation for possibly reducing the debt further. Sorry for being such a doubter. Sometimes desperation leads to the best solutions.

Everyone's talking about the Offer in Compromise, but don't forget about Currently Not Collectible status! If your boyfriend's finances are really tight right now, he might qualify to have his account temporarily placed in CNC status. The debt doesn't go away, but collections stop while he gets back on his feet. The IRS form is 433-F for individuals, and you basically need to show that after necessary living expenses, there's no money left to pay the tax debt. The benefit is immediate relief from collection activity, and sometimes the collection statute expires before they reassess your situation.

One thing nobody has mentioned is that your boyfriend should determine if he was misclassified as a 1099 contractor when he should have been an employee (W-2). If he was on the road 90% of the time doing work the company directed, used their equipment, followed their schedule, etc., he might have been misclassified. This is actually super common and if he was misclassified, he could file Form SS-8 for the IRS to make a determination. If they rule he should have been an employee, he'd only be responsible for the employee portion of FICA taxes (7.65%) instead of the full self-employment tax (15.3%). This could reduce his tax debt substantially!