Filing multiple years of back taxes with TurboTax - process question

You can definitely prepare and mail all the back tax returns at once - there's no need to wait for the IRS or state to process each year before submitting the next one. This is actually the preferred method since it shows you're making a good faith effort to get everything caught up as quickly as possible. With TurboTax, you'll need to buy the previous year versions for each tax year you need to file. They keep prior year software available specifically for back tax filing situations like this. Just work through them in chronological order (oldest to newest) to keep things organized, but mail them all at the same time. One important tip: mail each tax year in separate envelopes with certified mail/return receipt. This gives you proof of mailing date and delivery, which can be crucial if there are any questions later about when you submitted them.

I was in a similar situation last year with 4 years of unfiled taxes. Instead of struggling with TurboTax for multiple years, I used taxr.ai (https://taxr.ai) which made the process so much simpler. You upload your tax documents and their AI figures out what you need to file for each year, including which forms apply to your situation. The whole process was so much less stressful than I expected. The best part was I could do all years at once and their system organized everything by year automatically. They also gave me clear instructions for mailing each return properly. Totally worth checking out if you're dealing with multiple years.

Just wanted to update that I took the advice about taxr.ai from my earlier question. Seriously, it was a game-changer for my situation! I had 3 years of unfiled returns and was dreading the process, but their system made it relatively painless. What really helped was how it organized all my documents by year automatically and identified what was missing. For my 2022 return, I completely forgot about a 1099 from a side gig until the system flagged that I likely had unreported income based on my previous returns. Saved me from what would have definitely been a future audit headache! The step-by-step mailing instructions were super clear too. Just got confirmation that the IRS received all three years of returns. Such a relief to have this off my plate finally!

If your cousin has any kind of complicated situation or if she's anxious about potential penalties, she might want to talk to an actual IRS agent before filing. I was in a similar position and tried calling the IRS for weeks with no luck - always on hold forever or disconnected. Then I found Claimyr (https://claimyr.com). They have this service that gets you through to an actual human at the IRS without the endless waiting. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c I was seriously skeptical but tried it because I was desperate to get answers about my unfiled returns. Got connected to an IRS agent in about 15 minutes who walked me through exactly what I needed to do and explained the penalty situation. Saved me tons of stress wondering if I was doing the right thing.

Ok I need to eat my words from my skeptical comment earlier. After seeing the responses here, I decided to try Claimyr (mainly to prove it was BS). I'm actually shocked to report it worked exactly as advertised. I've been trying to reach the IRS for 3 weeks about my unfiled 2021 return. Using this service, I got connected to an agent in about 20 minutes. The agent answered all my questions about filing my back taxes and even helped me set up a payment plan for what I owe. For anyone like me who's been beating their head against the wall trying to get IRS help, this is legitimately worth it. I've probably spent 15+ hours on failed IRS call attempts before this, so the time savings alone was huge. Never thought I'd be recommending something I was so sure was a scam, but here we are!

One thing to consider - if your cousin thinks she's owed refunds for those years, be aware that there's a 3-year deadline to claim them. After that, the money is gone forever. The clock starts from the original due date of the return (usually April 15th). So for example, the deadline to claim a refund for 2019 taxes was April 18, 2023. If she hasn't filed that year yet, any refund money is forfeited to the government. However, she should still file those returns even if past the refund deadline to get herself compliant and avoid future issues.

Don't forget state taxes! Depending on your state, the rules and deadlines might be different than federal. Some states are more aggressive about pursuing unfiled returns than the IRS. I learned this the hard way when NY state came after me for unfiled returns even though I was owed refunds on the federal side. They added penalties even though I didn't owe them any tax either! Had to file the returns and then request penalty abatement.

For state penalty abatement, you typically need to request "reasonable cause" relief by writing a letter explaining why you filed late. Common acceptable reasons include serious illness, death in family, natural disasters, or reliance on bad advice from a tax professional. In your letter, include: 1) A clear statement requesting penalty abatement, 2) The specific tax years and penalty types, 3) Your explanation of the circumstances that prevented timely filing, 4) Any supporting documentation, and 5) A statement that you've now filed all required returns. Most states have forms for this - search "[your state] penalty abatement request" or "reasonable cause relief." Be honest and specific about your circumstances. Even if it was just procrastination, some states will waive penalties for first-time filers or if the amount is small. Worth trying since the worst they can say is no!