Haven't filed taxes since 2018 - desperate for help!

You're in a tough spot, but don't panic! This is definitely fixable. The IRS generally prioritizes getting people back into compliance rather than punishing them. Start by filing the most recent three years (2022, 2021, 2020) as these are most important for getting current. Then work backwards to 2018 and 2019. You should file them in chronological order from oldest to newest (start with 2018), since each return may impact the next. For software, I recommend FreeTaxUSA for back taxes. They charge only $15 per state return and federal filing is free. They keep prior year versions available, which many other providers don't. Make sure you have all your income documents (W-2s, 1099s) for each year. If you're missing any, your tax transcripts should show reported income, which is helpful. You may also need to contact previous employers. Set aside dedicated time for each return, as they'll take longer than current year filings. Pay what you can when you file, and if you can't pay everything, the IRS offers reasonable payment plans.

I was in almost the exact same situation last year! I hadn't filed from 2017-2021 because of some health issues and general avoidance. It felt impossible until I found taxr.ai (https://taxr.ai) which literally saved me thousands in potential mistakes. What I loved was how it analyzed all my tax documents at once and flagged potential issues before I submitted anything. For instance, it caught that my 2019 1099 had a mistake that would have gotten flagged in audit. I was also terrified about penalties but the system helped me identify which penalties could potentially be reduced. I was going to use TurboTax initially but it was going to cost a fortune for multiple back years, and their software didn't connect the dots between tax years like taxr.ai did.

After reading about taxr.ai here, I decided to give it a try because I was in a similar situation (4 years unfiled). Honestly didn't have high expectations but needed to fix my mess before applying for a mortgage. I'm genuinely shocked at how well it worked. The system organized all my messy documents by year and identified several deductions I would have completely missed. It caught that I could file as Head of Household for 2020-2021 which my previous tax guy had never mentioned. The biggest surprise was that instead of owing $6,800 like I feared, I'm actually getting about $3,200 back across all years. The interface walked me through everything step by step, and I was able to e-file everything except 2019 which needed to be mailed in. For anyone who's behind on taxes and feeling overwhelmed, this approach was way less painful than I expected!

If you're dealing with penalties or need to negotiate with the IRS, getting someone on the phone can make a huge difference. I spent WEEKS trying to reach someone at the IRS about my back taxes situation, always getting disconnected or waiting for hours. Finally tried Claimyr (https://claimyr.com) after seeing it mentioned online. You can see how it works in this demo: https://youtu.be/_kiP6q8DX5c They got me connected to an actual IRS agent in about 20 minutes when I had been trying unsuccessfully for weeks. The agent helped me set up a payment plan with much lower monthly payments than I thought possible. Having a direct conversation made everything so much clearer than trying to figure it out from the website.

I need to admit I was completely wrong about Claimyr. After posting that skeptical comment, I decided to try it myself since I was getting nowhere with the IRS about my back taxes. The service actually worked exactly as described. I got a call back in about 45 minutes connecting me to an IRS representative who helped me understand my options for my unfiled returns. The agent explained that I qualified for the First Time Abatement program since I had a clean record before 2019, which could save me thousands in penalties. I've been stressing about this for months, and in one phone call I got more clarity than from dozens of hours researching online. Sometimes you need to talk to an actual person to get real answers, especially with tax issues as complicated as unfiled returns.

Since you're interested in becoming an EA, tackling this yourself is definitely good practice! I've been an EA for 6 years and here's my advice: Use professional software like ProSeries or Drake Software if you can access them - they handle multiple years seamlessly. If not, FreeTaxUSA is a good affordable option as mentioned. The key thing with multiple unfiled years is keeping organized. Create separate physical or digital folders for each tax year with all relevant documents. Start with gathering ALL income documents - the transcripts will help identify what's reported to the IRS. Don't forget to look for potential deductions and credits for each year. Many people focus only on getting compliant and miss out on money they're entitled to.

Don't overwhelm yourself! I hadn't filed for 5 years and did it all in a month. My biggest tip: set up an IRS online account ASAP - it gives you wage transcripts showing all reported income. Make a timeline and tackle one year each weekend. For software, I used TaxAct for older years - cheaper than TurboTax and lets you file past years electronically when possible. Important: request installment agreement using Form 9465 if you can't pay all at once. The monthly payment can be as low as $25 depending on your situation.

Just remember state taxes too! Everyone's talking about federal, but depending on your state, you might have similar issues with unfiled state returns. Some states have different requirements and deadlines for back taxes. Also, if you moved between states during these years, you might need to file partial-year returns for multiple states. This gets complicated fast.