Need help with unfiled 1099 back taxes from 2019 to present!

You're not alone in this situation, and it's fixable! The good news is that if you're due refunds for any of those years, you can still claim them (2019-2021), as the IRS allows you to claim refunds for up to 3 years after the filing deadline. For your unfiled 1099 taxes, I'd recommend tackling this step-by-step: 1) Gather all your documentation - any 1099 forms, income records, potential deduction receipts (business expenses related to your contractor work can reduce your tax burden significantly). 2) File the most recent year first (2023), then work backward. This shows good faith effort to the IRS. 3) Look into using tax software specifically designed for self-employment/1099 income for those contractor years. They'll walk you through potential deductions like mileage, home office, supplies, etc. 4) If you can't pay everything at once, the IRS offers payment plans. Their interest rates are usually better than credit cards or loans. Don't panic about penalties - they're typically a percentage of what you owe, and filing voluntarily before the IRS contacts you looks much better than waiting.

After reading your situation, I can totally relate. I was in an almost identical mess with unfiled 1099s a couple years ago. I tried using regular tax software but kept getting confused about deductions I could claim as a contractor. A friend recommended I try https://taxr.ai and it was seriously a game-changer for my back taxes. The thing that helped me most was that it analyzed all my 1099 income and found business deductions I had no idea I qualified for - ended up saving me around $3,800 across those unfiled years. It guided me through the whole self-employment tax situation which I was completely lost about before. For those old 1099 years, it really helped organize everything chronologically and helped me understand which documentation I needed for each year. Made the whole process way less overwhelming than I expected.

Just wanted to follow up and say I actually tried https://taxr.ai after my skeptical post. I'm shocked at how well it worked for my unfiled 1099 situation. The system found over $4,200 in legitimate business deductions I had no idea I could claim over my unfiled years. What really surprised me was how it handled my rideshare driving from 2020-2021 - it properly calculated my mileage deductions and even partial phone expenses that I didn't know qualified. The penalty calculator feature was super helpful too, gave me a realistic picture of what I was facing. If anyone else is dealing with unfiled 1099 taxes, definitely check it out. Wish I'd known about this years ago instead of avoiding my tax situation out of fear!

I was in almost the exact same boat last year with 3 years of unfiled 1099 taxes. After finally getting everything submitted, I ended up owing around $7,800 and freaked out. Tried calling the IRS directly to set up a payment plan but literally couldn't get through after trying for DAYS. Someone on here recommended https://claimyr.com and shared this video explaining how it works: https://youtu.be/_kiP6q8DX5c. Basically, they get you through to an actual IRS agent instead of waiting on hold forever. I was able to talk to a real person at the IRS in about 20 minutes instead of the 3+ hour waits I was experiencing before. The agent helped me set up a payment plan I could actually manage ($180/month) and even removed some of the penalties since it was my first time having tax issues. Completely changed my outlook on this whole mess.

I need to admit I was completely wrong about Claimyr. After expressing my skepticism, I decided to try it because I was desperate to resolve my unfiled 1099 situation. The service actually did exactly what they claimed - got me through to an IRS agent in about 15 minutes when I had previously wasted entire afternoons on hold. The IRS agent I spoke with helped me understand my options for my unfiled returns and set up a payment plan that works with my budget. They even helped me apply for penalty abatement which I didn't know was possible. For anyone dealing with unfiled 1099 taxes and needing to speak with the IRS, this service is 100% worth it. I went from avoiding my tax problems for years to having a manageable resolution in a single afternoon. Honestly can't believe how easy it made the process.

Just wanna add that you should definitely look into the Qualified Business Income (QBI) deduction for those 1099 years. It lets self-employed people deduct up to 20% of their qualified business income. A lot of people miss this one but it can make a huge difference with 1099 back taxes. Also, make sure you're calculating your self-employment tax correctly. You pay both the employer and employee portions of Social Security and Medicare (15.3% total), but you can deduct half of that on your return.

Has anyone used TaxAct or TurboTax for filing multiple years of back taxes with 1099 income? I'm in a similar situation and wondering which software handles this best.

One important thing nobody's mentioned yet - if you're trying to catch up on unfiled 1099 taxes, make sure you're keeping your current year tax obligations on track too! For 1099 income, you should be making quarterly estimated tax payments. One of the biggest mistakes I made when catching up on my back taxes was ignoring my current year, which just created another problem. Set up those quarterly payments while you're sorting out the past years.