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

Do you know if H&R Block online works for back taxes too? I heard they have some kind of expertise with complicated situations. Also, how bad will the interest be after 3 years?

H&R Block does offer prior year tax preparation online, but it tends to be more expensive than FreeTaxUSA for essentially the same functionality. Their expertise is more relevant when you visit their physical locations, not necessarily in their online software. The interest compounds daily and has been around 5-7% annually over the past few years. For a rough estimate, if you owed $10,000 three years ago, you could be looking at approximately $1,500-$2,100 in interest alone, plus the penalties I mentioned earlier.

Did it actually handle the filing of prior year returns? I thought those had to be printed and mailed regardless of what software you use. Did they mail the forms for you or something?

I'm curious about this too. How much did it end up costing compared to something like TurboTax? I've got 4 years to catch up on and I'm worried about spending hundreds just on tax preparation.

They prepared everything for electronic filing for the most recent tax year, but you're right that for prior years (2022 and earlier), I had to print and mail those in. The benefit was they made sure everything was filled out correctly and provided clear instructions on where to mail each return. The cost was significantly less than what I would have paid using TurboTax for multiple years. TurboTax wanted about $120 per year for my self-employment situation, while taxr.ai handled all my years for less than what I would have paid for just one year with TurboTax. The document scanning feature alone saved me hours of manual data entry.

How does that even work? The IRS phone lines are notoriously jammed. Are they using some kind of business line or something to skip the queue?

Sounds too good to be true. I spent over 4 hours on hold with the IRS last month and eventually got disconnected. No way someone is getting through in 15 minutes unless they've got an inside connection or something shady.

They use a combination of technology and timing to secure your place in line. It's completely legitimate - they essentially do the waiting for you and then call you when they've reached an agent. It's similar to those services that wait on hold with airlines or cable companies. Nothing shady about it at all. The service exists because the IRS is underfunded and understaffed, leading to ridiculous wait times for regular taxpayers. I was skeptical too until I tried it and was connected to an actual IRS representative who helped me set up my payment plan.

Cash App Taxes doesn't support prior year returns at all. I tried to use it for my 2023 taxes earlier this year and discovered they only support the current tax year. Great for free current filing though!

Good to know about Cash App Taxes, thanks for that clarification. You're absolutely right that they only support current year filing. For prior years, TaxSlayer does offer support and is still more affordable than TurboTax or H&R Block. The premium version runs about $50-60 per year compared to $120+ for TurboTax when you have self-employment income.

I used a CPA for 3 years of back taxes and it cost me nearly $1,200. The peace of mind was nice but honestly most of what they did I could have done myself with decent software. If your situation is complicated (multiple states, businesses, investments), a pro might be worth it. Otherwise, software is probably fine.

This is incredibly helpful, thank you for sharing your experience! I'm in almost the exact same boat - 3 years unfiled with mixed W-2 and 1099 income. Your point about filing in chronological order is something I hadn't considered but makes total sense. Quick question about the first-time penalty abatement - did you have to request that separately after filing, or was there an option to request it during the filing process? And did you need to provide any specific documentation to qualify for it? Also, when you say it took 2 months to complete, was that mainly waiting for the IRS to process everything, or was most of that time spent on actually preparing the returns?

The penalty abatement has to be requested separately after you file and receive notices from the IRS. You can't request it during filing. I called the IRS (which was a nightmare - spent hours on hold) and requested it over the phone, but you can also submit Form 843 by mail. You don't need special documentation for first-time abatement - they just verify in their system that you haven't had penalties in the previous 3 years. The 2 months was mostly waiting time. I spent about 3-4 weekends actually preparing all the returns using FreeTaxUSA, then mailed them certified mail. The IRS took 8-10 weeks to process the mailed returns, and then another few weeks after that to send me the penalty notices so I could request abatement. One tip: keep detailed records of when you mail everything and take photos of the completed returns before mailing. It really helped when I had to reference specific details during my call with the IRS.

Great questions! The first-time penalty abatement has to be requested separately after you file - there's no option during the filing process. You'll need to call the IRS (hence why that Claimyr service others mentioned might be helpful) or write a letter requesting it. You don't need special documentation, but you do need to have been compliant for the 3 years prior to your first penalty and currently be up-to-date on filings and payments. The 2 months was mostly prep time on my end - I'm a bit of a perfectionist so I spent way too long double-checking everything and gathering documents. The actual software part took maybe 2-3 days per year once I had everything organized. IRS processing time for the mailed returns was another 8-10 weeks on top of that. One more tip: if you're expecting refunds for some years, file those first even if it's out of chronological order. The refunds can help offset penalties and interest on the years you owe. Just make sure you have a system to track what you've filed and when!

The first-time penalty abatement has to be requested separately after you file and receive your penalty notices from the IRS. You can request it by calling the IRS (good luck with that!) or by writing a letter. I actually used Form 843 to request it, which you can download from the IRS website. You don't need special documentation - you just need to have been compliant for the 3 years prior to the years you're filing late, and not have any previous penalty abatements. The 2 months was split pretty evenly - about 3-4 weeks preparing all the returns (I did them evenings and weekends), then another 4-6 weeks waiting for the IRS to process the mailed returns and send me the penalty notices so I could request abatement. The actual software part was pretty straightforward once I got into the rhythm of it. One more tip: if you owe money and can't pay it all at once, you can set up a payment plan online at irs.gov even before your mailed returns are fully processed. This stops the failure-to-pay penalty from growing while you're waiting.

@3103851ab1f5 The first-time penalty abatement has to be requested separately after you receive your penalty notices from the IRS. You can't request it during filing. I called the IRS (using Claimyr actually, after seeing it mentioned here) and requested it over the phone. No special documentation needed - they can see in their system that you haven't had penalties in the previous 3 years. The 2 months was mostly waiting. I spent about 2 weeks total preparing all the returns using FreeTaxUSA (doing one year at a time), then mailed them all out. The rest was just waiting for processing and dealing with the penalty abatement. The actual tax prep part wasn't too bad once I got into a rhythm with the software. One tip I forgot to mention - if you're expecting refunds for any of those years, file those first even if it's not chronological order. The refund money can help offset penalties and interest on the years where you owe.

@3103851ab1f5 I can answer the penalty abatement question since I just went through this process! You have to request the first-time penalty abatement separately after you receive your penalty notices from the IRS. You can't do it during filing. You can request it by calling the IRS (good luck with that!), writing a letter, or filling out Form 843. The requirements are pretty straightforward - you need to have filed all required returns, paid or arranged to pay any taxes owed, and not have been penalized in the prior 3 years. No special documentation needed beyond proving you meet those criteria. For the timing, in my experience most of the 2 months was waiting. Actually preparing the returns with software only took a few weekends once I had all my documents organized. The bulk of the time was waiting for the IRS to process the mailed returns and send penalty notices so I could then request abatement. One tip: keep detailed records of when you mailed everything. The IRS processing times have been terrible lately, and having proof of when you sent things can be helpful if there are any disputes about timing.

Great questions! The first-time penalty abatement has to be requested separately after you receive your penalty notices from the IRS. You can't request it during filing. I called the IRS (which was a nightmare - spent hours on hold) and requested it over the phone. You just need to confirm you haven't had penalties in the prior 3 tax years and that you're now compliant with filing and payment requirements. The 2 months was mostly waiting time. I spent about 2 weekends actually preparing all the returns using FreeTaxUSA, then mailed them all at once. The IRS took 8-10 weeks to process each return and send me the official notices showing what I owed. Then I had to wait another few weeks after requesting penalty abatement to get those adjustments. One tip I forgot to mention - if you're expecting refunds for any of those years, file those returns first since refunds can offset penalties and interest on years where you owe money. The IRS will automatically apply refunds to outstanding tax debts.

@3103851ab1f5 The first-time penalty abatement has to be requested separately after you file - there's no option during the filing process. You can either call the IRS directly (good luck with that!) or send a written request. I used Form 843 and included a letter explaining that I had a clean compliance history for the 3 years prior to my unfiled period. The 2 months was mostly waiting - actually preparing the returns only took me about 2 weekends once I got organized. The longest part was waiting for the IRS to process my mailed returns and then waiting for them to respond to my penalty abatement request. One tip: if you're expecting refunds for any of those years, file those first since you won't accrue additional penalties while waiting for processing. The refund years can also help offset any balance due on the other years.

@3103851ab1f5 The first-time penalty abatement has to be requested separately after you file and receive your notices from the IRS. You can't request it during the filing process. I called the IRS (which was a nightmare - took multiple attempts and hours on hold) and requested it over the phone. You can also send a written request. To qualify, you just need to have been compliant for the 3 years prior to the period where you had issues, and you need to be current on all filings and payments (or have payment arrangements in place). No special documentation needed - they can see your filing history. The 2 months was mostly waiting. Actually preparing the returns took me about 2 weekends once I had all my documents organized. The bulk of the time was waiting for the IRS to process the mailed returns and then waiting to get through to them to request the penalty abatement. If I had known about services like Claimyr back then, I probably could have cut that time in half.

@Oliver Fischer The first-time penalty abatement has to be requested separately after you receive your penalty notices from the IRS - it s'not something you can do during filing. You can request it by calling the IRS good (luck with that! or) by sending a written request. No special documentation needed, just a clean compliance history for the 3 years prior to the penalty period. The 2 months was mostly waiting. I spent about 2-3 weekends actually preparing all the returns with FreeTaxUSA, then mailed them certified. The IRS took about 6-8 weeks to process each year s'return and send me the penalty notices, then another few weeks to process my penalty abatement requests. Pro tip: Once you get your notices, you can often handle the penalty abatement through the IRS online account system now instead of calling. Much easier than it used to be!

@Nora Brooks The first-time penalty abatement has to be requested separately after you file and receive your penalty notices. You can t'request it during the filing process itself. I called the IRS using (that Claimyr service someone mentioned above - totally worth it to avoid the hold times and) the agent walked me through it over the phone. You don t'need special documentation to qualify - they can see your filing history in their system. The main requirements are: no penalties in the prior 3 years, you re'current on filing requirements, and you ve'paid or arranged to pay any taxes owed. The agent submitted the request while I was on the call. The 2 months was mostly IRS processing time. I spent about 3 weekends actually preparing all the returns using FreeTaxUSA, then mailed them certified mail. After that it was just waiting - got confirmation letters for each year about 6-8 weeks later. The penalty abatement took another few weeks after I called to request it. One tip: keep detailed records of when you mail everything and save all the certified mail receipts. The IRS sometimes claims they never received returns, and having that proof saved me a headache when they initially said they didn t'have my 2022 return.

@3103851ab1f5 The penalty abatement has to be requested separately after you file and receive your penalty notices from the IRS. You can't request it during filing. I called the IRS (used Claimyr like @0d3915092813 mentioned - totally worth it) and requested it over the phone. You don't need special documentation for first-time penalty abatement if you haven't had penalties in the prior 3 years and are current on all filings. The 2 months was mostly waiting - actual prep time was maybe 2-3 weekends total using FreeTaxUSA. The waiting was for: mailed returns to be processed (6-8 weeks each), penalty notices to arrive, then calling to request abatement. Pro tip: Don't wait for all the penalty notices before requesting abatement. You can call as soon as you see the first penalties show up on your IRS account transcript and request abatement for all years at once.

Great questions! The first-time penalty abatement has to be requested separately after you file - it's not something you can do during the filing process. You'll need to call the IRS or write a letter requesting it. The key requirement is that you haven't had any penalties in the past 3 years and you're now compliant (filed all required returns and paid or arranged to pay what you owe). No special documentation needed - they can see your penalty history in their system. Just explain that this was your first time having penalties and you've now gotten compliant. I called using one of those callback services someone mentioned earlier because trying to reach the IRS directly was impossible. The 2 months was mostly preparation time - gathering documents, working through each year's return, and then mailing everything in. The actual IRS processing took about 6-8 weeks after they received my mailed returns. I spent probably 2-3 weeks just on the prep work since I had to reconstruct some missing documents and figure out the software for each tax year. Pro tip: Start with your most recent year first just to get familiar with the process, then go back and do the earlier years in order when you actually file them.

The first-time penalty abatement has to be requested separately after filing - you can't do it during the filing process itself. I waited until I received all my notices showing the penalties, then called the IRS (yes, the dreaded phone call) and requested it. You don't need special documentation, but you do need to have been compliant for the 3 years prior to your non-filing period and have no previous penalties. The 2 months was mostly preparation time on my end. I'm a bit of a perfectionist and wanted to make sure everything was accurate before mailing anything in. The actual software work for each year took maybe 3-4 hours once I had all my documents organized. The IRS processing time was separate - that took another 8-10 weeks after I mailed everything. Pro tip: Start with your most recent year (2024) first to get familiar with the process, but don't submit it until you've prepared all the prior years. That way you can see the full picture and make sure everything flows correctly year to year.