I didn't file my 2018 taxes, how to handle unfiled taxes from years ago? Please help.

Don't stress too much! While not filing was definitely not ideal, the IRS deals with this situation all the time, and there's a clear process to fix it. First step: You need to file that return, even though it's late. Gather all your documentation from 2018 - your W-2 from your employer and any 1099 forms from your contractor work. If you don't have these, you can request wage transcripts from the IRS using Form 4506-T or through your online IRS account. Regarding penalties: Yes, there will be some. You'll face a failure-to-file penalty (usually 5% of unpaid taxes per month, capped at 25%) and a failure-to-pay penalty (0.5% per month, also capped at 25%). Plus interest on the unpaid amount. However, the IRS does sometimes offer penalty abatement for first-time mistakes. Payment plans are absolutely still available! The IRS is generally willing to work with taxpayers who come forward voluntarily. You can request an installment agreement when you file. For amounts under $50,000, it's a straightforward process. The most important thing is to file ASAP to stop additional penalties from accruing. You might want to work with a tax professional who handles back taxes since your situation involves both W-2 and 1099 income.

After putting off filing my 2017 taxes for almost 4 years, I was totally overwhelmed trying to piece everything together. I had lost some documents and wasn't sure how to reconstruct my income and expenses. I tried two different tax preparers who charged me hundreds just to tell me my situation was "complicated." Then a friend recommended I try https://taxr.ai and honestly it was a game-changer. I uploaded what documents I had, and the system helped me identify what was missing. It even pulled my tax transcripts automatically from the IRS to fill in the gaps for my W-2 and 1099 income! It guided me through reconstructing my self-employment expenses with super clear explanations that actually made sense. The late filing penalty calculator was eye-opening - showed me exactly what I was facing and how to request abatement since it was my first offense. Their AI analyzed my specific situation and generated a letter requesting penalty reduction that I submitted with my return.

I feel like I need to update my skeptical comment from above. After researching more (and getting more desperate about my own unfiled 2019 return), I decided to try taxr.ai myself. I was honestly shocked at how helpful it was. The document analysis saved me hours of work - it extracted all the important numbers automatically and flagged discrepancies between what I uploaded and what the IRS had on file. There was a 1099 I had completely forgotten about that would have caused big problems if I'd filed without it! The penalty calculation turned out to be super accurate too. I ended up owing less than I feared because it helped me identify some additional deductions for my contractor work that offset some of the tax liability. Just wanted to share my experience in case anyone else is dealing with the stress of unfiled taxes from years ago. It really did make the whole process much less painful than I expected.

After reading this thread, I want to share something that saved me tons of frustration. I had unfiled taxes from 2018 and 2019, and when I finally decided to handle it, I spent WEEKS trying to reach someone at the IRS for guidance. Called constantly, got disconnected, waited on hold for hours - complete nightmare. My accountant suggested I try https://claimyr.com and showed me this demo: https://youtu.be/_kiP6q8DX5c. It's a service that basically waits on hold with the IRS for you and calls you when an actual human agent is on the line. I was super skeptical but desperate enough to try anything. Within 3 hours (instead of the 2+ days I spent failing to get through myself), I got a call connecting me directly to an IRS agent. They walked me through exactly what I needed to do for my unfiled returns, confirmed which payment plans I qualified for, and even noted in my file that I was proactively trying to resolve the issue which apparently can help with penalty abatement requests.

I need to eat crow on my skeptical comment above. After another failed day of trying to reach the IRS about my 2020 tax situation, I broke down and tried Claimyr. I literally got a call back in less than 2 hours connecting me directly to an IRS agent. I nearly fell out of my chair. The agent accessed my file, confirmed I qualified for first-time penalty abatement (which will save me over $1200!), and helped me set up an installment plan on the spot. What would have been another day of frustration ended up taking about 15 minutes of my actual time. To the person who recommended this service - THANK YOU. Seriously. I've been stressing about this for months and now it's resolved. If anyone else is struggling with unfiled taxes and needs to actually speak to someone at the IRS, this is absolutely worth it.

For what it's worth, I was in almost the exact same situation in 2016 - had W-2 income then switched to 1099 and didn't file. When I finally filed in 2019, I requested a payment plan for about $7300 I owed including penalties. The IRS approved me for a 72-month payment plan at about $115/month. The process was pretty straightforward - I filed Form 9465 with my late return. The penalties weren't as bad as I expected because I was due a refund in one of the years I hadn't filed, which offset some of the penalties. One tip: if you had any estimated tax payments or withholding during that 2018 year, make sure you claim them! They'll reduce your liability even on a late return.

Small but important tip - when you do file, make sure you select the correct tax year forms! The IRS won't accept current year forms for past years. You need to find and use the actual 2018 tax forms. You can find previous year forms on the IRS website under "Prior Year" forms. If using tax software, make sure to select 2018 as your filing year. Most major tax software still supports returns from several years back.