Thanks for the tip! Will I need any specific documentation from Fidelity if I make this IRA contribution now for last year? And should I reduce the contribution amount since we'll only get 10% back?

You don't need any special documentation from Fidelity for your tax return. When you make the contribution, just make sure you specify it's for the 2023 tax year. Fidelity will eventually send a Form 5498, but that usually comes after the tax filing deadline and isn't needed to claim the credit. As for reducing the contribution amount, I'd still recommend contributing the full amount to reach $2,000 total. Even though you're only getting 10% back as a direct credit ($200), remember that traditional IRA contributions also reduce your taxable income. So you're getting both the $200 credit AND the tax deduction on your contribution, which at your income level could save you another 22% or so in taxes on that money.

I amended last year for exactly this reason! It was a bit of paperwork but totally worth it in my case. Got back about $280 between the credit and the deduction on a $1,400 contribution. Just filed Form 1040-X with the corrected info and Form 8880 for the credit.

Thanks for sharing your experience! $280 back on $1,400 is pretty good. I think I'm gonna go ahead with the amendment. I hate leaving money on the table, even if it's just a couple hundred bucks.

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.

Do paper I-bonds still exist? I thought Treasury phased those out years ago. And if I get paper bonds through my tax refund, how would I convert them to electronic later?

Paper I-bonds do still exist, but ONLY through the tax refund process. It's the only way to get them since Treasury Direct otherwise went fully electronic. To convert paper bonds to electronic, you'd use the Treasury Direct "SmartExchange" feature after creating an account. You fill out a form with your paper bond information, mail the bonds to Treasury, and they add them to your electronic account. It takes a few weeks for processing, but then you can manage them online like any other Treasury Direct holdings. Some people actually prefer this method since the paper bonds can be held for safekeeping and don't require online account access until you're ready to redeem them.

The Taxpayer Advocate Service saved me too! But they're super backed up these days... took almost 2 months to get an appointment at my local office. Definitely worth trying though, just don't expect immediate help.

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.

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.