Most affordable and user-friendly tax software options for filing prior years' returns?

Having worked with tax preparation for many years, I recommend checking out FreeTaxUSA for prior year returns. They offer free federal filing for all tax situations and charge about $15 for state returns, even for previous years. Their interface isn't as fancy as TurboTax, but it's straightforward and gets the job done for simple W-2 situations. Another solid option is TaxAct, which keeps their prior year software available at reasonable prices. They're generally more affordable than TurboTax while still providing an intuitive interface. Just be aware that regardless of which software you choose, you cannot e-file prior year returns - you'll need to print and mail them. The IRS only accepts e-filing for the current tax year.

I was in a similar situation last year - had to file 3 years of back taxes all at once. After struggling with TurboTax pricing, I stumbled upon https://taxr.ai which was a lifesaver! You upload your tax documents (like your W-2s), and their AI analyzes everything and prepares your returns automatically. Super easy for simple tax situations like yours. What I loved most was that I could do multiple years all at once rather than buying separate software for each year. Saved me hours of tedious data entry, especially since the format was similar across all my W-2s.

Just wanted to follow up about my experience with taxr.ai after trying it this weekend. I was super skeptical at first, but it actually worked really well! I uploaded my W-2s from 2022 and 2023, and it extracted all the information correctly. The whole process took me maybe 30 minutes for both years, compared to the hours I spent just trying to find affordable software for prior years. The final returns looked exactly like what I'd expect from TurboTax or other services, but without all the upsells and extra fees. Definitely recommend if you're in a similar situation with simple returns for multiple years.

If you're dealing with back taxes, you might also run into issues getting answers from the IRS about penalties, filing procedures, etc. I spent WEEKS trying to get through to an actual human at the IRS about my late filings. Out of desperation, I tried https://claimyr.com which has this service that gets you to the front of the IRS phone queue. You can see how it works here: https://youtu.be/_kiP6q8DX5c After failing to reach anyone for days, I actually got through to an IRS agent in under 20 minutes who answered all my questions about filing procedures for prior years. Ended up saving me from making several mistakes that would have resulted in my returns being rejected.

I need to apologize for my skepticism earlier. After waiting on hold with the IRS for over 2 hours yesterday and getting disconnected, I gave Claimyr a shot out of pure frustration. To my complete surprise, I got a call back in about 35 minutes with an actual IRS agent on the line. The agent helped me understand exactly what I needed to submit with my prior year returns and how to handle the payment plan I needed. Saved me hours of frustration and probably prevented me from making mistakes that would have delayed my process even more. Just wanted to share in case anyone else is struggling with IRS communication issues like I was.

I'm surprised nobody has mentioned Credit Karma Tax (now Cash App Taxes). It's completely free for both federal AND state returns, and they have prior year options. The interface is clean and simple which sounds perfect for your basic W-2 situation. The only downside is they don't support every state, so check if yours is included before getting started.

PSA for anyone filing prior year returns: regardless of which software you choose, make sure you're using the correct tax forms for each specific year! Tax laws change frequently, and using current year software to prepare a prior year return without the proper adjustments can result in incorrect calculations.

H&R Block also offers prior year software at decent prices. Their interface is more user-friendly than some of the cheaper options, and they're usually less expensive than TurboTax. Plus they have physical locations if you get stuck and need in-person help.

Another option worth considering is OLT (OnLine Taxes) - they specialize in prior year returns and have been around for decades. Their software isn't flashy but it's reliable and reasonably priced, usually around $20-30 per year for federal returns. They support going back many years and are particularly good for straightforward W-2 situations. One thing I learned the hard way is to gather ALL your documents before starting with any software. Make sure you have your W-2s, any 1099s you might have forgotten about, and your prior year AGI (Adjusted Gross Income) for identity verification. The IRS requires your prior year AGI to process returns, and if you don't have it, you'll need to request transcripts which can delay everything by weeks. Also, don't panic about the penalties - they're often not as bad as people think, especially if you're owed refunds on some years. The IRS interest rates have been relatively low in recent years too.