Thank you for this suggestion! I hadn't even thought about paper filing as an option. Do you know if there's any additional form I need to fill out since the electronic extension was rejected? And how long does it typically take for the IRS to process a paper extension?

You don't need any additional forms - just the standard Form 4868 for extension. Write a brief note in the margin referencing the electronic rejection if you want, but it's not required. Paper processing is taking about 3-4 weeks right now according to what I've heard, but the postmark date is what matters for filing on time, not when they process it. Just be sure to estimate your taxes properly and include payment if you owe. The extension gives you more time to file, but any taxes owed were still due on April 15th. Keep a copy of everything and the certified mail receipt in your records.

YES! TurboTax kept rejecting my roommate's return for "duplicate filing" but when he called, they admitted it was a glitch in their system, not the IRS. They had to escalate it to their tech team and it took 3 days to fix. Might be worth calling TurboTax support directly to see if it's a known issue.

This is terrible advice. The IRS expects ALL income to be reported regardless of amount or whether you received a form. Intentionally not reporting income is tax evasion. The penalties for getting caught are way worse than just paying the tax you owe now.

That's just what my tax preparer told me. I'm not saying it's for everyone. Obviously if you're worried about it, go ahead and report it. I'm just saying from a practical standpoint, the IRS isn't conducting audits over small amounts especially when there's no paper trail. They focus their limited resources on bigger fish. But everyone should make their own decision based on their comfort level with risk.

I honestly have no idea what he did with his business taxes. We haven't really talked much since I stopped helping out. I'm guessing he probably didn't report it since he specifically mentioned it was "under the table" when I asked about tax forms.

The friend could also get in trouble for not properly classifying workers and paying employment taxes. So many small business owners don't realize they can't just pay people cash without consequences. They need to either treat them as employees and withhold taxes or properly document independent contractors with 1099s.

Can you still do a Solo 401k if you have another W2 job with a 401k already? I thought there were limits to how much you could contribute across all your accounts.

You can absolutely have both a Solo 401k and an employer 401k, but you're right that there are some limitations. The $23,000 employee contribution limit (for 2025) applies across ALL your 401k accounts combined. So if you've already maxed out your employer 401k, you can't make additional employee contributions to your Solo 401k. However, the employer contribution portion of your Solo 401k is completely separate and not affected by your W2 job's 401k. You can still contribute up to 25% of your net self-employment income as the "employer" portion to your Solo 401k, even if you've maxed out your other 401k.

Does Quickbooks handle calculating the home office deduction well? I've heard that's one of the trickier deductions to get right and I don't want to raise audit flags.

Thanks for that, though it makes me feel even worse knowing they're just sitting on my money! Do you know if they at least apply the unclaimed refunds to the federal deficit, or does it just go into some general fund?

It goes into the general Treasury fund from what I understand. So technically it's reducing the deficit by contributing to general government revenue, but it's not specifically earmarked for debt reduction. The whole situation definitely sucks. If it makes you feel any better, you're far from alone - the IRS reports that they have billions in unclaimed refunds every three-year deadline. The system absolutely doesn't make it easy for people.

That's not accurate. If you're owed a refund, there's no penalty for filing late. The IRS only issues failure-to-file penalties when you OWE them money and don't file. They don't penalize people for not claiming money the IRS gets to keep.

Did you have any issues with the I-9 process though? An ITIN doesn't provide work authorization, so I'm curious how you handled the employment eligibility verification requirement.

That's a completely separate issue from tax compliance, and you're right to bring it up. Getting an ITIN only addresses the tax identification requirement, not work authorization. For employment eligibility, each business has to determine their own approach based on their understanding of applicable laws. Some of our workers were able to adjust their status through various programs and eventually obtained work authorization. Others transitioned to providing services through their own small businesses where they had multiple clients (not just us).

Yes! We used a Certified Acceptance Agent for our farm workers' ITIN applications and it was much smoother. The agent verified their original identification documents on the spot, so they didn't have to mail in passports or birth certificates. The processing time was about 5 weeks instead of the usual 7-9 weeks when submitting directly to the IRS. The agent also helped make sure the tax returns filed with the applications were properly prepared, which prevented delays from errors. It cost a bit more but was totally worth it for the faster processing and reduced headaches.