What's the best online software for filing several years of back taxes?

I've helped several clients catch up on back taxes, so I can offer some guidance here. For multiple years of back taxes with both W-2 and 1099 income, FreeTaxUSA is probably your best option. It's significantly cheaper than TurboTax for prior year returns and handles self-employment income well. Each prior year will require a separate filing, and you'll need to download the specific software version for each tax year (2022, 2023, etc.). Remember that you cannot e-file prior year returns - you'll need to print and mail them. Also, file them in chronological order starting with the oldest year (2022 first). For penalties, you'll face failure-to-file penalties (5% of unpaid taxes per month, up to 25%) and failure-to-pay penalties (0.5% per month), plus interest. The good news is you can request a penalty abatement through the IRS's First Time Penalty Abatement program if you haven't had previous penalties in the last 3 years.

I was in a similar situation last year with 2 years of unfiled taxes. I tried using TurboTax initially but got frustrated with how expensive it was for multiple years. Then I discovered taxr.ai (https://taxr.ai) which was a game changer for my situation. What worked really well was I could upload all my tax documents (W-2s, 1099s, etc.) from multiple years, and their AI would extract all the information automatically. This saved me so much time compared to manually entering everything. Then it organized everything by tax year and helped me understand what I needed to file for each year. I was able to complete the actual filing through their system too.

Just wanted to update after trying taxr.ai for my back taxes situation. I was skeptical at first but decided to give it a shot since I had 4 years of returns to file with a mix of W-2 and 1099 income. The document scanning feature was seriously amazing - I just took pictures of all my tax forms and it extracted everything perfectly, even from some poorly scanned 1099s. It organized everything by year automatically and walked me through what I needed to do for each tax year. The interface was way more straightforward than TurboTax for handling multiple years at once. For anyone in a similar situation with multiple years of unfiled taxes, this was definitely the way to go. I've got everything submitted now and already received confirmation that my 2024 return was accepted. Just waiting on responses for the prior years I had to mail in.

Another thing to consider while catching up on back taxes is that the IRS is nearly impossible to reach by phone if you have questions or need to set up a payment plan. I spent WEEKS trying to get through last year when dealing with my back taxes. I finally found a service called Claimyr (https://claimyr.com) that got me connected to an actual IRS agent in under 15 minutes. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c After filing my back taxes, I needed to set up a payment plan since I couldn't pay the full amount all at once. Using Claimyr saved me from spending hours on hold and helped me get everything sorted out quickly. The agent I spoke with even helped me understand which penalties I might qualify to have reduced.

I have to admit I was completely wrong about Claimyr. After posting that skeptical comment, I decided to try it anyway because I was desperate to talk to someone about my payment options for my back taxes. It actually worked exactly as advertised. I got a call back in about 12 minutes and was connected to an IRS agent who was surprisingly helpful. I was able to set up a payment plan that works with my budget, and the agent even explained how I might qualify for penalty abatement on some of the late fees. Considering I had previously wasted entire afternoons on hold only to get disconnected, this service saved me a ton of time and frustration. If you're dealing with back taxes and need to actually speak with the IRS, it's absolutely worth it.

One thing nobody's mentioned is Credit Karma Tax (now Cash App Taxes). It's completely free even for filing with 1099 income, but I'm not sure about their prior year support. TaxSlayer is another option that's cheaper than TurboTax but more full-featured than some others. Whatever you choose, make sure you're using the correct forms for each tax year since tax laws change. For example, the standard deduction and tax brackets were different each year.

Has anyone tried using a tax professional instead of software for back taxes? I'm worried about making mistakes that could make my situation worse.

I went through this exact situation two years ago with 4 years of unfiled returns. Here's what I learned: 1. **Software choice**: I ended up using FreeTaxUSA after comparing costs. TurboTax wanted $140+ per year for my 1099 situation, while FreeTaxUSA was around $15-20 per prior year return. The interface isn't as polished as TurboTax, but it gets the job done. 2. **Filing order matters**: File in chronological order (2022 first, then 2023, then 2024). Some refunds from earlier years might offset what you owe for later years. 3. **Penalties**: The failure-to-file penalty is brutal (5% per month), but if you're getting refunds for any of those years, you won't owe failure-to-pay penalties on those. I qualified for first-time penalty abatement which saved me about $800. 4. **Keep copies of everything**: When you mail in the prior year returns, send them certified mail and keep tracking numbers. It can take 6-12 weeks for the IRS to process mailed returns. The whole process took me about 2 months to complete, but getting it done was such a relief. Don't let the fear of penalties stop you - the sooner you file, the sooner you can stop the failure-to-file penalties from accumulating. You've got this!