Will receiving 10k+ checks trigger Form 8300 reporting requirements for banks?

But what if the buyer decides they want to pay in cash instead of certified checks? Would that change things? I had a similar situation once and got really confused about what I needed to report.

If the buyer pays in cash over $10,000, then yes, that changes things significantly. You (as the recipient) would be required to file Form 8300 with the IRS within 15 days of receiving the cash. This applies to a single cash transaction over $10,000 or multiple related transactions that total over $10,000. For installment payments made in cash, if you know from the beginning that the payments will exceed $10,000, you need to file Form 8300 when the total exceeds that threshold. But certified checks, cashier's checks, money orders, and bank transfers don't trigger Form 8300 filing requirements for the person receiving them.

How exactly does this work? Do they give actual tax advice or just general information? I've got some big payments coming in from a side business and getting nervous about what I need to report.

I'm skeptical that any online tool could really give accurate advice on something this specific. Wouldn't you need to talk to an actual tax professional who knows all the details of your situation?

It's more sophisticated than just general information - you upload your documentation and the AI analyzes the specific details of your situation. It pointed out that while Form 8300 wasn't required for my non-cash transaction, I still needed to report the income on Schedule D since I was selling collectibles at a profit. It even flagged that I might qualify for a lower capital gains rate based on how long I'd owned the items. The system also creates documentation explaining your situation in case you ever need to show why you handled reporting a certain way. It's definitely more personalized than generic advice websites but still more affordable than hiring a CPA for a consultation.

So does this actually work? How does some service manage to get through when the IRS phone lines are always jammed? Seems too good to be true.

This sounds kinda sketchy tbh. Why would you need to call the IRS in advance about a perfectly legitimate deposit? Feels like you're just asking for trouble or unnecessary scrutiny.

It absolutely works - they use an automated system that handles the waiting and phone tree navigation for you. When an actual IRS agent picks up, you get a call connecting you directly. No magic, just technology that saves you from having to personally wait on hold for hours. I called because I wanted clarity directly from the IRS about reporting requirements for a situation similar to the OP's. Getting official guidance gave me peace of mind, and the agent actually confirmed I didn't need to file anything special for my certified check deposits. Sometimes talking to the source is the best way to avoid making mistakes based on internet advice (including mine!).

That's a good point about reporting the income. My company provided a written statement that employees can sell the old equipment and keep 100% of proceeds. Would this count as a gift from my employer or as regular income? I'm thinking it might be considered a bonus and taxed at that rate.

This would almost certainly be considered taxable income, not a gift. The IRS generally doesn't consider transactions between employers and employees to be gifts - they view them as compensation for services. Since your employer is allowing you to sell company property and keep the proceeds, the fair market value of those electronics would likely be considered additional compensation and reported on your W-2 as taxable wages. Alternatively, your employer might treat it as a bonus, which would also appear on your W-2 but might be subject to higher withholding rates.

Would splitting the deposits into smaller amounts help avoid this scrutiny? Like if OP deposited $9k at a time instead?

@Katherine Hunter - Absolutely DO NOT do that! What you re'describing is called structuring "and" it s'actually a federal crime. The Bank Secrecy Act specifically makes it illegal to break up large transactions into smaller amounts to avoid reporting requirements. Banks are trained to watch for this pattern and will file SARs if they suspect structuring. You could face serious penalties even if the underlying money is completely legitimate. Always deposit legitimate funds normally and transparently - trying to fly "under the radar will" only create bigger problems.