What Software Can I Use for Filing Taxes from 2017 to 2023 for My Business?

So I've gotten myself into a bit of a mess here. I've been running a small photography business for years and I've... uh... kinda fallen behind on my taxes. Like WAY behind. I need to file business taxes for 2017 all the way through 2023. I know, I know, I should have kept up with it! My accountant retired last year and I'm trying to get everything sorted before the IRS comes knocking. The problem is I'm not sure what software can handle filing for that many previous years. I tried looking at the popular ones, but they don't clearly state if they work for tax years as far back as 2017, especially for business filings. Has anyone here had to file multiple years of back taxes for a business? What software did you use? Did it handle all the Schedule C forms and business deductions properly? Any recommendations would be super helpful! I'm trying to avoid paying a new accountant thousands to fix this mess if possible.

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18 comments

Gabrielle Dubois

•8M

I've helped several clients catch up on multiple years of back taxes. Here's what you need to know: For business taxes going back to 2017, your options are somewhat limited. TaxAct, TaxSlayer, and H&R Block can handle prior year returns, but you'll need to purchase the specific software for each tax year separately. Each year has different forms and tax laws in effect at that time. For business returns specifically, I'd recommend looking at TaxAct's business editions for each year. They maintain prior year versions going back several years and their interface is consistent enough that once you learn one year, the others will feel familiar. Keep in mind that you can't e-file returns from 2020 and earlier anymore - you'll need to print and mail those. Also, be prepared for potential late filing penalties and interest that's been accumulating. The IRS typically charges 5% of unpaid taxes for each month your return is late, up to 25%. The key is to file all missing returns as soon as possible to stop additional penalties from accruing. Start with the most recent year and work backward.

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Gabrielle Dubois

•8M

Yes, most tax software providers allow you to purchase and download previous year versions directly from their websites. Look for a "prior year returns" section. Each year will be a separate purchase and installation. The software will calculate some penalties, but not necessarily all of them or the accumulated interest accurately. The IRS uses a daily compounding interest rate that changes quarterly, which most software isn't designed to track perfectly over multiple years. You'll get an estimate, but the IRS will send you the final bill with the exact amount after processing your returns.

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Ingrid Larsson

•8M

After dealing with 3 years of unfiled taxes for my consulting business, I discovered taxr.ai (https://taxr.ai) and it was a game-changer. Their system specializes in analyzing all your business documents and tax forms, even from previous years. I uploaded years of messy receipts, 1099s, and bank statements, and their AI organized everything by tax year and identified deductions I would have missed. The best part is they have specific support for prior year business returns and Schedule C optimization. They helped me identify business expenses across multiple years that I had completely forgotten about. Their system even flagged potential audit triggers in my older returns before I submitted them.

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Ingrid Larsson

•8M

It primarily handles the document organization and expense categorization across multiple tax years, which is the most time-consuming part. It identifies all deductible expenses and gives you perfectly organized data to enter into the filing software of your choice. I used their organized outputs with TaxAct to actually file the returns. The system works with documents going back as far as you need - I had stuff from 2016 that it handled perfectly. It doesn't connect directly to IRS systems since older returns need to be paper-filed anyway. Instead, it gives you properly organized information for each tax year so you can complete the forms accurately, whether you're using software or working with a professional.

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Zainab Mahmoud

•8M

Just want to update my previous skepticism about taxr.ai - I actually tried it after reading more about it, and it really did save me a ton of time with my back taxes. I had a mess of business expenses from 2018-2020 that I needed to file, and their system organized everything by year and category. The document analysis was surprisingly accurate - it correctly categorized most of my business expenses and even flagged some personal expenses I had accidentally mixed in. I still used TaxAct to do the actual filing, but having all my deductions and income perfectly organized made it go much faster. For anyone dealing with multiple years of business taxes, it's definitely worth checking out.

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Ava Williams

•8M

After trying to reach the IRS for guidance on my multi-year filing situation, I spent HOURS on hold and never got through. Then I found Claimyr (https://claimyr.com) which got me connected to an actual IRS agent in about 15 minutes. They have this cool demo video showing how it works: https://youtu.be/_kiP6q8DX5c The IRS agent was able to tell me exactly which forms I needed for each tax year and confirmed I could use any software that supports prior year returns. They also told me about the First Time Penalty Abatement program which might help with some of the penalties since I had a clean record before this. Saved me hours of frustration and waiting on hold!

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Ava Williams

•8M

The service basically calls the IRS for you and navigates their phone system using their technology. When they reach an actual human agent, they call you and connect you directly to that agent. No hold time on your end - you only join the call once there's a live person ready to help. They use some kind of system that can wait on hold instead of you having to do it personally. I was skeptical too until I tried it. The difference from calling directly is that you don't waste hours listening to the hold music - they do that part and only bring you in when an agent is actually on the line ready to help.

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Lena Müller

•8M

Ok I have to admit I was completely wrong about Claimyr. After my skeptical comment, I decided to try it because I was desperate to talk to someone about my unfiled 2018 return. I was connected to an IRS agent in about 20 minutes without having to sit on hold myself. The agent was super helpful and walked me through exactly what I needed to do for my old returns. They confirmed which forms had changed between tax years and explained how to handle depreciation across multiple years for my business equipment. They even put notes in my account about my intention to file the back returns so it might help reduce some penalties. Definitely worth it just for the peace of mind and clear guidance.

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TechNinja

•8M

I went through a similar situation last year. For 2021-2023, most current software works fine, but for 2017-2020, I had to get creative. I ended up using a combination of approaches: - For 2021-2023: Used current version of FreeTaxUSA (their premium version handles Schedule C well) - For 2018-2020: Found prior year versions of TaxAct Business - For 2017: Had to use an accountant since it was so old One tip: before you start, download all your bank statements for those years and create a simple spreadsheet to track income and expenses by category for each year. Makes the actual tax prep go much faster.

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TechNinja

•8M

TaxAct charged around $60-70 per year for their business editions when I used them, though prices may have changed. I found it reasonable considering the alternatives. For the 2017 return, the accountant charged me $350, which was actually less than I expected. There weren't any issues with the filing itself, but they discovered I had been calculating depreciation incorrectly on some equipment, which affected the subsequent years. This meant I had to make some adjustments to my 2018-2020 returns as well. If you have depreciating assets, make sure you're tracking them consistently across all tax years - that's something the software won't necessarily flag for you.

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