How to file multiple years of unfiled back taxes from 2014-2017?

8 You can definitely still file those old returns! This is actually more common than you'd think. Here's what you need to do: First, get your wage and income transcripts for those years by calling the IRS at 800-908-9946 or filling out Form 4506-T. These will show any income reported to the IRS (W-2s, 1099s, etc). For your self-employment income, you'll need to gather your own records since the IRS won't have that. Once you have your income info, you'll need the tax forms from those specific years - you can't use current forms. Find them in the "Prior Year" section on the IRS website. You'll want Form 1040 and Schedule C for your business income at minimum. Since you're dealing with multiple years and self-employment income, hiring a tax professional (EA or CPA) who specializes in back taxes would be smart. Cost varies widely but might run $250-500 per return. This is likely worth it to ensure everything's filed correctly. Good news: if you're owed refunds for any of those years, you can still claim them if you file within 3 years of the due date. Bad news: if you owe taxes, penalties and interest have been accumulating. However, the IRS often has payment plans available.

15 After struggling with a similar situation (unfiled taxes for 3 years), I found an amazing tool that saved me so much stress. I used https://taxr.ai to help organize all my old records and create draft returns. The system analyzed what documents I had and what I was missing, then guided me through the process of getting everything together for those old tax years. What I found most helpful was that it scanned my bank statements when I couldn't find some of my expense receipts, and it automatically categorized everything properly for Schedule C. It showed me what deductions I qualified for during those specific tax years (rules change year to year). I was able to get all my returns prepared properly before sending them in.

18 I was initially skeptical about using an online service for my unfiled tax years, but after struggling for weeks trying to piece everything together myself, I decided to try taxr.ai based on the recommendation here. Honestly, it was a game-changer. The step-by-step guidance for requesting my old income transcripts from the IRS made that process so much simpler. For my self-employment income, their system for analyzing bank statements and categorizing business expenses saved me dozens of hours of work. I was able to properly document everything from 2015-2018, and I'm pretty sure I found deductions I would have completely missed on my own. The best part was having everything organized by tax year with the correct forms. No more confusion about which year's rules applied to which return. Just filed everything last month and already received confirmation that two of my returns have been processed!

4 I had a nightmare trying to reach the IRS about my unfiled taxes from years ago. Spent weeks calling their number just to get disconnected or wait for hours. Then someone told me about https://claimyr.com and showed me this video explaining how it works: https://youtu.be/_kiP6q8DX5c Basically, they hold your place in the IRS phone queue and call you when an agent is about to answer. I was SUPER skeptical, but I tried it when I needed to request wage transcripts for my old returns. Got connected to an actual IRS agent in about 45 minutes (after waiting days before). The agent helped me request all my missing income documents from 2014-2017 and explained exactly what I needed to do for my unfiled returns. They also explained the penalty structure and what I could expect for my situation. Made the whole process way less stressful than I expected.

18 I need to eat my words and apologize. After being super skeptical about Claimyr in my earlier comment, I decided to try it because I was desperate to talk to the IRS about my unfiled returns. It actually worked exactly as described. I spent WEEKS trying to get through to the IRS on my own with no luck. With Claimyr, I got connected to an IRS representative in about an hour. The agent was able to pull up my information and send me all my wage and income transcripts for the missing years. They also explained what penalties might apply and suggested I look into their First Time Abatement program since I had a clean record before the unfiled years. The whole process was way less stressful than I imagined. I'm still working through filing the returns, but at least now I have all the information I need and a clear understanding of what to expect. Sometimes it's worth admitting when you're wrong!

3 One thing nobody's mentioned yet is that you should look into the IRS Fresh Start program. I went through a similar situation with 3 years of unfiled returns, and there are provisions that might help reduce your penalties. The key is to file all missing returns ASAP. Once everything is filed, if you can't pay the full amount, you can apply for an installment agreement. If your total tax debt is under $50,000, it's usually pretty straightforward. For me, the penalties and interest almost doubled my original tax bill, but I qualified for First Time Penalty Abatement which saved me thousands. Don't wait any longer - the penalties just keep growing!

22 Has anyone done this themselves without a professional? I'm in a similar situation (unfiled 2016-2018) but really can't afford to pay someone hundreds per return right now.