Has anyone actually had experience with the IRS coming after someone for unfiled returns when they were owed money? My cousin was in a similar situation (5 years unfiled) but never heard anything from the IRS. I always figured they only care if you owe them money???

I went through this exact situation with my own adult child two years ago - 8 years of unfiled returns! Here's what worked for us: 1. Start with the most recent 3 years FIRST (2024, 2023, 2022) since these can still get refunds. We used TurboTax's prior year versions which made it much easier. 2. Get organized - create a folder for each tax year and gather all documents systematically. The IRS wage transcripts mentioned above are a lifesaver for missing W-2s. 3. Don't try to do all years at once - we did one year per weekend to avoid burnout and mistakes. 4. The good news: since your son had taxes withheld, he likely won't face penalties and is probably owed money for those recent years. 5. For the older years beyond the refund window, we filed them all together after finishing the "money years" first. Total recovery for my child was over $7,000 from just the 3 eligible years! The peace of mind was worth even more. You're being a great parent helping him get compliant. It's overwhelming at first but very doable if you break it down year by year.

Question for anyone who's gone through this - did you use a CPA or just tax software for catching up on multiple years? I'm in a similar boat (5 unfiled years) and wondering if it's worth paying a professional or if software is good enough for straightforward W-2 income.

Miguel, I was in almost the exact same situation as you about 2 years ago - 7 unfiled years, also went through a divorce that triggered the whole mess. The good news is that since you've had taxes withheld and likely qualify for refunds, you're not going to face the scary penalties that people who owe money get hit with. Here's what worked for me: Start with the most recent 3 years FIRST since those are the only ones where you can still claim refunds. I used FreeTaxUSA for the older years since they have previous year software available for cheap (like $15 per state return). For the really old years where you've lost the refund window, you still need to file them but there's less urgency. Don't stress about hiring a tax attorney - that's overkill for your situation. A CPA could help but honestly if it's just W-2 income, you can handle this yourself. The IRS is actually pretty reasonable when you're catching up voluntarily and not hiding from them. The hardest part is just starting. Once you file that first return, the momentum builds and it gets easier. You've got this!

Has anyone here successfully claimed the R&D credit for software that ultimately didn't work out? We spent about $120k developing a specialized analytics tool but ultimately abandoned it because we couldn't solve some key technical problems. Can we still claim the R&D credit even though the project failed?

@Rajiv Kumar - Based on what you've described, your custom SaaS development sounds like it has strong potential for R&D credit qualification. The key factors working in your favor are: 1) creating new functionality not previously available, 2) solving technical challenges, and 3) having your developer document the process. However, I'd recommend being extra careful about a few things given your setup. Since you're using an outside developer, make sure your contract clearly establishes that you retain substantial rights to the software and bear the financial risk of the project. The IRS scrutinizes contractor arrangements closely for R&D credits. Also, with the Section 174 changes mentioned by Ryan Kim, you'll need to capitalize and amortize your $75k investment over 5 years starting in 2022, but you can still claim the R&D credit in the year the expenses were incurred. This actually makes the credit more valuable since you're getting an immediate credit against expenses that are now spread over multiple years. One practical tip: if you do move forward with claiming the credit, consider getting professional help with the documentation. The IRS four-part test requires very specific language and evidence, and it's easy to miss subtle requirements that could trigger an audit or disqualification.

Has anyone considered a multiple support agreement? I was in a similar situation where me and my brother both supported our disabled sister. Neither of us provided more than 50% alone, but together we provided over 100% of her support. We used Form 2120 and alternated who claimed her each year.

This is such a helpful thread! I'm dealing with a similar situation with my disabled brother. One thing I wanted to add that hasn't been mentioned yet - if your siblings receive any government benefits like SSI or SSDI, make sure to check if those count toward their "gross income" for the qualifying relative test. From what I understand, SSI payments generally don't count as taxable income, but SSDI might depending on the total amount and other factors. This could affect whether your working sibling exceeds that $4,700 income threshold. Also, Diego, since you mentioned your father only receives Social Security and doesn't file taxes, you might want to confirm he's not eligible to claim them first before you do. Even if he doesn't file, he might still have the right to claim them as dependents if he wanted to file. Keep detailed records of everything - I use a spreadsheet tracking every expense I cover for my brother throughout the year. Makes tax time so much easier!

My extension request last year wasn't accepted until April 17th (two days after the deadline) but I still didn't get any penalties because I submitted on April 14th. The IRS system gets super bogged down right at the deadline so delays are normal. Your submission date is what matters!!!!

I went through this exact same panic last year! Filed my extension on April 14th through FreeTaxUSA and didn't get confirmation until April 18th. I was freaking out thinking I'd get hit with penalties, but everything turned out fine. The key thing to remember is that the IRS considers your extension "filed" the moment you hit submit, not when they send you confirmation. As long as you submitted before midnight on April 15th (which you did on April 13th), you're protected from the failure-to-file penalty. Since you included your estimated tax payment of $2,300 with the extension, you should also be protected from most late payment penalties. The IRS is pretty reasonable about this - they know their system gets overwhelmed right at the deadline. Keep your submission confirmation from TurboTax as proof of your filing date. That timestamp is gold if you ever need to dispute any penalties. You did everything right - try not to stress about it!