I've never heard of this safe harbor rule before. Does this apply even for relatively small amounts like $900 in interest? That seems like overkill for the IRS to expect quarterly payments on such small amounts.

Yes, technically the safe harbor rules apply regardless of the amount. However, in practice, for relatively small amounts like $900 in interest resulting in under $200 in additional tax, the penalty would be very minimal - we're talking maybe a few dollars at most. The IRS calculates the penalty based on how much you underpaid and for how long. Since the interest is usually earned throughout the year, the penalty isn't on the full amount for the full year. Many people with smaller amounts of interest income don't worry about making quarterly estimates because the potential penalty is so small, but technically you're supposed to cover your tax obligations as you earn income.

I used TurboTax to amend my return last year when I forgot about a 1099-INT. It was pretty straightforward - I just logged back into my account, selected "amend return," and followed the prompts to add the missing info. The downside is they charge extra for amendments, I think it was like $50 when I did it.

Thanks for sharing! That $50 fee is still less than what most tax preparers charge, so that might be worth it. Did TurboTax handle submitting the amendment electronically or did you still have to print and mail it?

No formal purchase requisition, just noted in my accounting software as planned expenses and allocated the funds. Based on what everyone's saying, sounds like I definitely recorded these too early and should move them to 2025. Good catch on the distinction though!

Yeah, that's what I thought. Without formal documentation creating an actual obligation, it's just a planned expense, not an incurred one. For future reference, if you want to legitimately recognize expenses in a particular tax year, you need to create that obligation before year-end. A simple purchase order or signed contract dated before December 31st would have made those valid 2024 expenses even if you didn't pay until 2025. This is a common strategy for businesses wanting to accelerate deductions.

For cash basis, this is all moot - you record when you pay, period. That's the beauty of cash accounting for small businesses. But OP specifically mentioned they're using accrual, which has all these timing rules we're discussing.

Thanks for this explanation! Yes, the site did take a small fee during the conversion to ETH. Should I be including that fee in my calculations somehow? Sorry if that's a dumb question, I'm still trying to wrap my head around all this.

That fee is important! It should be factored into your cost basis. For example, if you withdrew $1000 worth of winnings but only received $950 in ETH after the fee, your cost basis should be $950, not $1000. When you eventually sell that ETH, you'll calculate your gain/loss based on the $950 figure. The $50 fee isn't deductible separately - it's just part of the transaction cost of acquiring the ETH. This is likely contributing to why your software is showing a capital loss.

How did you figure out the exact price when you received it though? The price can change like every minute and im never sure what exact value to use.

Wait seriously? I had no idea about Form 1096! Is that something I can just download from the IRS website? And does it need to be mailed or can I submit it electronically somehow?

Yes, Form 1096 is required when submitting paper 1099s to the IRS. It's essentially a cover sheet that summarizes all the 1099s you're submitting. You can download it from the IRS website, but it needs to be the official red-ink scannable version - a regular printout won't be accepted. For your situation, you might want to consider e-filing instead. If you e-file your 1099, you won't need the 1096 at all. There are several IRS-approved e-filing services that make the process pretty straightforward, and it's generally faster and eliminates the risk of mail delays. Plus, you get confirmation when the IRS receives your submission.

Does the contractor copy have the same deadline? Like, are you penalized separately for sending it late to the contractor versus sending it late to the IRS?

This is really interesting! I've never heard of a Qualified Disclaimer before. Is this something that can be done even years after being added to a deed? My husband has been on his father's deed since 2002, so about 20 years now. Would it still be possible to do this so close to the sale?

Unfortunately, a Qualified Disclaimer typically needs to be executed within 9 months of when the interest was created or when you turned 21 (whichever is later). Since your husband has been on the deed for around 20 years, this option probably won't work in your situation. There are still other approaches though. One possibility is having your father-in-law give your husband's share back to him as a gift before the sale (though this has gift tax implications). Another is to ensure proper documentation that your husband is acting as a "nominee" owner only. This would require specific language in the closing documents and proper reporting on tax returns.

I used TurboTax Premier last year for a capital gains situation with multiple owners (sold my parents' house where I was on the deed). It handled the basic reporting fine, but I found it didn't ask enough detailed questions about ownership intent or primary residence status for each owner. I ended up having to manually override some entries and add explanatory statements. Unless your situation is very straightforward, I'd recommend at least consulting with a tax professional who specializes in real estate transactions before trying to DIY it.

Thanks for the feedback. That's pretty much what I was worried about. I think I'll use a tax pro this year since the stakes are high, then maybe try software again next year when I don't have such complicated issues.