How far back should I go when filing back taxes? Need advice for catching up

Thanks for this info! Question though - if I file the last 3 years and get my refunds, but don't file years 4-6 back, could the IRS come after me later for those? And would I face penalties even if I was owed refunds for those older years?

The IRS could technically request any unfiled returns regardless of whether you've caught up on recent years. However, filing the most recent returns does often satisfy them if you weren't purposefully evading taxes. If you were due refunds for those older years (4-6 years back), you wouldn't face penalties since penalties are calculated as a percentage of taxes owed. But you would lose those refunds after the 3-year window closes. The unfortunate reality is that the government keeps refund money if you don't claim it within the time limit, even if it was rightfully yours.

Did it help figure out which forms you needed to file for each year? I did some contract work and I'm confused about all the different schedules and forms.

How accurate was it with the refund estimates? I'm worried about getting my hopes up about refunds and then ending up owing instead.

It automatically identified all the necessary forms based on my income sources. For my W-2 income it was straightforward, but it also recognized that I needed Schedule C for my freelance work and Schedule SE for self-employment taxes. It even flagged some business expenses I could deduct that I hadn't thought about. The refund estimates were surprisingly accurate. I was initially skeptical too, but the final numbers after filing with my accountant were within about $50-100 of what the tool predicted for each year. It takes into account your withholding and estimated tax payments to give a pretty realistic picture of what you'll owe or get back.

Wait, how does this service even work? Sounds too good to be true. The IRS phone system is literally designed to make you give up.

Yeah right, like some third-party service has magical access to IRS phone lines. They probably just take your money and tell you to keep waiting like everyone else.

It uses an automated system that continually redials the IRS using their algorithms to find the best times to call, then holds your place in line. You literally get a text when an agent picks up, then you jump on the call. No magic access - just smart technology that navigates their frustrating phone system better than a human can. They don't promise immediate access - sometimes it still takes a few hours, but the difference is you're not actively waiting on hold. You can go about your day, and your phone rings when an agent is actually available. It saved me from wasting an entire day on hold.

Is it better to do it yourself or hire a regular accountant for back taxes? I'm worried about making mistakes but don't want to get scammed.

For straightforward situations with mainly W-2 income, doing it yourself with tax software is definitely doable and will save you a lot of money. Most tax software handles prior year returns, though you might need to pay for each year separately. If you have more complicated situations like self-employment income, rental properties, or investments, a regular CPA might be worth it - expect to pay around $200-500 per past return depending on complexity. Just be clear about pricing upfront and avoid anyone advertising "pennies on the dollar" tax settlements or using scare tactics about IRS enforcement.

Good point! Does each state have different rules for how far back you need to file?

This is such helpful advice! I'm in a similar boat and wondering - how long did it take you to get those wage and income transcripts from the IRS? I've been dreading calling them because I've heard horror stories about wait times. Also, did you end up filing all 6 years or just the 3 most recent ones after you got your refunds? I'm trying to figure out if it's worth the stress to go back the full 6 years if the older ones might not have much impact.

Getting the wage and income transcripts was actually one of the most frustrating parts! I tried calling the IRS directly first and literally could not get through after multiple attempts over several weeks. Either busy signals or hours on hold with no answer. I ended up using one of those callback services someone mentioned earlier in this thread (Claimyr) and got through in about 2 hours. The transcripts themselves were available immediately once I talked to an agent - they can mail them or give you the info over the phone if you verify your identity. As for filing, I did end up going back the full 6 years to be safe. The older years (2017-2019) showed I owed small amounts but the penalties were minimal since I filed voluntarily before the IRS came after me. Honestly, the peace of mind of being completely caught up was worth the extra effort. But if you're really stressed about it, starting with the recent 3 years and seeing how you feel is totally reasonable!

@PixelPioneer Getting the wage and income transcripts was actually one of the biggest pain points! I tried calling the IRS directly first and it was a nightmare - literally spent 4+ hours on hold over multiple attempts before giving up. I ended up using the online transcript tool on the IRS website, but you need to verify your identity which can be tricky if you don't have certain types of accounts or credit history. For the filing strategy, I ended up doing all 6 years to be safe, but honestly I probably could have gotten away with just the recent 3-4 years. The older years (2017-2018 for me) had very small amounts owed - like under $200 each including penalties. If you're mainly worried about compliance and the older years won't have big impacts, you could always start with the recent ones and see if the IRS even asks about the older years. One tip that saved me a lot of stress: I started with just one year (2022) to get the process down, then it was much easier to tackle the rest. The first one is always the hardest!

I can share my experience with getting those transcripts! It took me about 2-3 weeks when I requested them online through the IRS website (you need to verify your identity first), but honestly calling was faster when I finally got through - got them within a few days. The online option is less stressful if you're not in a rush. I ended up filing all 6 years to be completely compliant, but in hindsight I probably could have stopped at 4-5 years. The oldest years (2018-2019 in my case) had minimal impact - tiny amounts owed that weren't worth the stress. If I had to do it again, I'd prioritize the 3 most recent for refunds, then maybe go back 1-2 more years just to be safe. The peace of mind from being completely caught up was worth it for me, but everyone's situation is different. You could always start with the recent years and see how it goes!