My husband is 1099. He’s a contractor. He hasn’t kept up with a single expense/ mileage etc in years. I’ve filed separate from him the last 4 years but he needs to file the last 6- he probably needs more (I’d guess he hasn’t filed in 10 years) but IRS needs last 6 to be compliance. We kind of just have to bite the bullet since he didn’t keep up with his expenses and just use basic mileage for his work only truck, phone, insurance and guess for some supplies. Monthly he uses roughly $800 for paint, tools, hardware etc. so we just plan to say that. (200 weekly on supplies)
He is now keeping up with all his mileage, hotels, expenses etc. but has NO proof for his past. He used a lot of cash. Do we need concrete proof if we are writing off for the tools, paint etc that $800 monthly?
My other question is. To tackle the other years would you do it all at once file 6 years at once or go ahead and file for 2025 and work my way back?
Would filing this year trigger the IRS to see his unified taxes in past years.
To be clean he has not made over 60k any years, so this is bad BUT not like he’s some big baller.
What’s the best game plan? Any advice?
Posted by No_Till4303
10 Comments
File in order of oldest years first, but file 2025 by the deadline.
You may be able to reconstruct some of the expenses from old bank statements. Banks will often export statements as .csv files which can be opened in Excel.
File 2025 immediately, then 2024, and 2023 since you can still claim your refund (if any). Then go back and file the oldest known not filed tax return. Then work your way up from there.
Have you received a notice from the IRS? Why are they asking for six years to be in compliance?
IANAL but you need to get one. Your story sounds really messy and you need one to help you straighten this out.
Don’t forget estimated tax payments for 2026 (due 4/25, 6/15, 9/15, 1/15)
Get a tax pro.. with. legal in the room.
You can and will pay for this but you are innocent spouse so protect yourself.
That sounds super frustrating.
Just FYI, the IRS doesn’t care about verbal agreements, it goes by who the child lived with more nights. So if she was with you more in 2025, you’d generally be the one who can claim HoH.
If you both file, the IRS will sort it out based on proof. But yeah, it really comes down to whether it’s worth the potential drama on the co-parenting side.
He will owe a fortune. 15.3% of his net income after expenses that he has receipts for just for self employment tax, plus fed and state income tax.
Probably need to hire a tax professional to work it all out. Maybe they can do something with at least his credit card charges. And, he needs to not use cash for business expenses.
Please work with a CPA to do this! They will definitely know exactly what to claim as far as expenses go and will be well worth the money.
Okay, this is fair amount to digest but I will try to lay it out the best I can. I am not a CPA this is just my advice.
1.) Do not allow the infield returns to continue, stop the bleeding. So, file tax year 2025 before or by midnight 04/15/26. Before this date is ALWAYS better for you. That includes paying before 04/15/26 or getting on a payment plan before or on that date.
2.) This is going to hurt to hear but for all 6 years your husband will have penalties & interest due to not filing & or paying if he owed. So, unfortunately, the return that is the oldest will have the most accrued penalties & interest.
3.) If I were in your shoes & all the unfolds returns were filed “correctly”, I would request an “offer in compromise” & request a for the penalties & interest to be waived. If you have the ability to full pay the balance(s) when filing or after the unfolded returns have processed, even better!
4.) I would STRONGLY suggest having 2020 through 2024 prepared professionally. 2025 needs to be filed, you can circle back to that with a CPA & amended it later on. This is definitely a situation I would recommend to talk over & work through with a professional. More than likely whomever you contact will determine if 2020 – 2024 can be filed all at once or will have to filed separately.
5.) More documentation/information is always better than less when it comes to taxes
6.) If you would prefer for your CPA be the sole communicator w/the IRS, there is route to go with that as well. Which I would recommend discussing with your CPA.
7.) Also, you can make payments now towards the infield returns, if you are waiting to hear back about a payment plan or waiting for them to process fully.
Good luck, hope that helped. 🤙