Thank you so much! I'll send you a message right away. When you implemented it, what was the most challenging part for a very small operation? And did you find any particular resources helpful for the risk assessment portion?

The most challenging part was definitely creating reasonable security controls for customer data without breaking the bank. Simple things like implementing password managers and enabling two-factor authentication gave us big security improvements without major costs. We also created a very basic security training that takes about 20 minutes to go through with new employees. For the risk assessment, NIST has a publication called "Small Business Information Security: The Fundamentals" (NISTIR 7621) that was incredibly helpful. It has a straightforward approach to identifying your most important information assets and the realistic threats to those assets. Much more practical than the enterprise-focused guides I found elsewhere.

Great question about applicability. A WISP is legally required in some states (like Massachusetts) for any business that collects personal information of residents, regardless of size. In other states, requirements vary. However, even when not strictly required by law, many client contracts and cyber insurance policies now require a documented security program. So it really depends on what kind of information the business handles, where their customers are located, and what contractual obligations they have. Since the original poster mentioned it's required for a new client, that's likely a contractual requirement rather than a statutory one.

Did you get the full amount you were expecting? I'm worried because mine says "approved" but with a slightly different amount than I calculated.

Yes, I got exactly the amount shown on the "Where's My Refund" tool. If your approved amount is different than what you calculated, the IRS probably made an adjustment to your return. This happens a lot - they might have caught a math error or determined you qualified for a different credit amount than what you claimed. The good news is that once it shows "approved" with a specific amount, that's what you'll get deposited. You should receive a letter in the mail explaining any adjustments they made to your original return.

Thanks for the tip! I'll definitely check early morning. My credit union sometimes posts government payments early too. Feeling less anxious now hearing everyone's experiences.

Oh god, I hadn't even thought about that! Is the self-employment tax calculated on the gross 1099 income or after deductions? And what's the estimated tax penalty usually amount to?

Self-employment tax is calculated on your net profit after deductions (thankfully). So all those business expenses will reduce both your income tax and SE tax. That's why maximizing legitimate deductions is so crucial for 1099 workers. The estimated tax penalty varies based on how much you should have paid quarterly and current interest rates. It's basically an interest charge for not making timely payments throughout the year. It won't be your biggest concern compared to the failure-to-file and failure-to-pay penalties, but it's another thing that adds up. Form 2210 calculates this penalty, and sometimes you can get it waived if you have a reasonable cause, but after 5 years that might be difficult.

This is actually super important. If the IRS has already sent notices of deficiency or started collections, the approach is completely different than voluntary disclosure.

I didn't even think about the Head of Household status! Does that make a big difference in the tax calculation? And would I still qualify for that even if I end up letting her claim our daughter as a dependent this year?

Yes, Head of Household status makes a significant difference! For 2024 taxes (filed in 2025), the standard deduction for HOH is $21,900 versus just $14,600 for Single filing status. That's a $7,300 difference in taxable income right off the bat, which could save you thousands depending on your tax bracket. You can still qualify for Head of Household even if you let your ex claim your daughter as a dependent, as long as your daughter lives with you more than half the year and you pay more than half the cost of maintaining the home. The dependent exemption and Head of Household status are separate benefits.

Does that alternating years agreement need to be part of the formal custody arrangement, or can it just be a separate signed document between the two parents?

Thanks for this explanation! This makes so much more sense now. So even though my Airbnb isn't a "rental activity" under passive activity rules, I still report it in Box 2 because it's physically real estate. Does this mean I might be limited in how I can use the losses though? Our partnership is showing about $13,500 in losses this year.

Yes, you've got it exactly right - Box 2 is for the real estate itself regardless of how it's classified under passive activity rules. Regarding your losses, that's where the Pub 925 classification becomes important. Since short-term rentals (average stay <7 days) are considered "nonrental activities," you'll need to determine if you materially participate in the business. If you do materially participate (like managing bookings, coordinating cleanings, etc.), then the losses are nonpassive and can offset your other income like wages. If you don't materially participate, then the losses are passive and can only offset passive income.

I had this exact problem with TurboTax last year. You need to go into the income section, then after entering the rental income/expenses, there should be a question about average rental period. Make sure you select "7 days or less" if that applies to your Airbnb. TurboTax should then reclassify it properly. The income still shows in Box 2, but it gets the proper treatment for passive activity purposes.