I completely forgot about the basic life insurance! You're right, I think we do get enrolled in that automatically. And now that I think about it, I did sign up for the dental plan this year. Would that show up in box 12 dd too? How would I figure out the breakdown of what's included in that number?

Yes, dental would definitely be included in box 12 DD as it's considered part of your health benefits package. Life insurance would also be there if it's employer-provided. The best way to get a breakdown is to contact your HR or benefits department and ask for an itemized list of what makes up that $4,350 figure. They should be able to show you exactly how much is attributed to dental, life insurance, and any other benefits. They typically have this information readily available since they had to calculate it to put on your W-2 in the first place.

That's not accurate. Box 12 DD should only include the actual cost of employer-sponsored health coverage, not potential or hypothetical coverage values. If OP truly has no health benefits through the employer, this code shouldn't appear with a value. This is why checking with HR is important - it's either an error or there are benefits OP is not aware of.

Does the Opportunity Zone investment have to be made immediately after selling the software? Are there timing requirements like with a 1031 exchange? This sounds interesting.

You have 180 days from the date of sale to invest in a Qualified Opportunity Fund to defer the capital gains from your software sale. Unlike a 1031 exchange, you only need to invest the gain portion, not the entire proceeds. The key timing requirements are the 180-day investment window, and then the holding periods: hold for 5 years and you get a 10% reduction in the deferred gain; hold for 10+ years and any new appreciation on the opportunity zone investment itself becomes completely tax-free. This could be especially valuable if you're buying a vacation rental that you expect to appreciate significantly.

Did he use a qualified intermediary? I've heard that's essential for doing these exchanges properly.

17 Do you actually attach a physical note to the return? Or is there a specific form for name changes that should be included?

11 If you're filing electronically (which most people do now), there's no need for a physical note. There's usually a section in most tax software where you can explain special circumstances, but it's not even really necessary. For paper returns, you can include a brief statement with your return explaining the timing of your name change. There's no specific form required just for a name change situation like this. The most important thing is making sure your current legal name (your married name) is what you use on the tax return itself, and that your SSN is correct on all documents.

10 You should be fine. The IRS usually processes returns pretty quickly, and they'll match based on your SSN. But if you're concerned, you might want to keep an eye on your return status using the "Where's My Refund" tool on the IRS website.

Wait, really? That would be amazing. Do I have to specifically ask for this program by name when I contact them? And would I qualify even though I had the extension and still missed it?

Yes, you should specifically ask for "First Time Penalty Abatement" when you contact them after filing. Don't rely on them to offer it - many IRS agents won't mention it unless you ask. You would likely still qualify despite missing your extension deadline. The main requirement is having a clean compliance history for the three prior tax years (meaning you filed and paid on time, or had valid extensions and paid by those deadlines). The IRS sees this as a one-time courtesy for otherwise compliant taxpayers.

I'm so sorry about your mom. I was in a similar situation with my father's passing. The IRS does have something called "reasonable cause" for penalty relief. You'll need to attach a letter explaining the circumstances and showing how the death and estate duties prevented you from filing on time. Include any documentation you can (death certificate, executor appointment papers). In my experience, they were actually pretty understanding.

Thanks for pointing this out! I hadn't even considered the liability aspect. So how should I properly document the transfer if I decide to move some of my stock profits into my business? Is there a specific form or process?

You should create a written resolution documenting the capital contribution or a formal loan agreement if it's structured as a loan. For a capital contribution, create a simple document stating the amount, date, and purpose that you're contributing capital to the business. Keep this with your company records. If you structure it as a loan, create a proper loan document with terms, interest rate (use the applicable federal rate at minimum), and repayment schedule. Then make sure your business actually makes the payments according to the schedule. This is more complicated but can be advantageous in certain situations if you want to pull the money back out later without tax consequences.

I used TurboTax last year with a similar situation. It does have separate sections for capital gains and business expenses, but it doesn't specifically guide you on the relationship between them. I had to know myself that they needed to be reported separately. The software doesn't warn you about taking stock profits and using them for business stuff - you have to understand that concept yourself.