That's a really good point I hadn't thought about. Do you know if this restriction is common in most company option plans? I'll have to go back and read the fine print on my grant documents.

In my experience, it's fairly common for private companies to have some transfer restrictions. Most option plans allow transfers to family trusts or estate planning vehicles with notice to the company, but often prohibit transfers to third parties without approval. The reason is that companies want to control who their shareholders are, especially while private. If you're planning to transfer to a trust, review your option agreement and stock option plan carefully. Look for sections titled "Transfer Restrictions" or "Transferability." Sometimes you just need to give written notice to the company, other times you need formal approval from the board or compensation committee.

Wait I thought 83(b) elections were only for restricted stock, not options? I'm confused because my accountant told me options aren't eligible for 83(b) since they're already taxed at exercise.

Thanks for mentioning this! I didn't realize there was a checkbox specifically for multiple jobs. Do you know if checking that box results in the same withholding as calculating the extra amount manually? I'm wondering if one method withholds more accurately than the other.

The checkbox generally works well if both jobs have similar pay levels. It essentially tells your employer to withhold taxes as if you're single (which is higher) rather than married, which compensates for having two incomes. If there's a big difference between your incomes, or if you have other income sources like investments or rental properties, the manual calculation might be more accurate. The checkbox is basically a simpler but slightly less precise approach. I chose it because I didn't want to recalculate every time we got raises or bonuses - the checkbox automatically adjusts when your income changes.

I've used it for three years straight and it's been pretty accurate for me. Last year it predicted a $720 refund and we got back $678. The year before it was within about $200. You have to make sure you're including ALL income sources though. If you have investments, side gigs, or anything that doesn't have withholding, that could explain why your results were off.

Thanks for sharing your experience. Maybe I need to check my inputs more carefully this time. I think part of the problem might have been that I got a bonus halfway through the year that messed up the calculations, and I also had some stock sales I didn't account for properly. I'll try the calculator again and make sure I'm including everything. It's reassuring to hear it can actually be accurate when used correctly!

Thank you for bringing this up - I hadn't even thought about withholding! Does the school typically report scholarship/grant info to the IRS? Or would they only know if I report it? And how would I even calculate how much I should pay in estimated taxes?

Yes, schools report your scholarship and grant information to the IRS using Form 1098-T, which shows your tuition and related expenses as well as scholarships/grants received. So the IRS does know how much you received, even if you don't report it. This is why people sometimes get letters from the IRS later asking about unreported income. For calculating estimated taxes, you'd need to figure out approximately how much of your scholarship/grant money will be used for non-qualified expenses (the taxable portion), then calculate the tax on that amount based on your tax bracket. The IRS has worksheets in the Form 1040-ES instructions to help with this. Since you're a dependent, your tax situation might be affected by the kiddie tax rules depending on your total income.

Is there a specific form we need to use for reporting scholarship income? I don't see anything specific about this on the 1040.

The program definitely had us working under faculty mentors! We didn't direct our own research - we were assigned to projects and supervised the whole time. I do have the acceptance letter that specifically calls it a "research stipend" and mentions it covers living expenses during the program. Would that help?

That acceptance letter is exactly the kind of documentation you need! It clearly shows this was a stipend, not self-employment income. Keep that letter and make a copy to include with your tax return. The fact that you worked under faculty supervision further strengthens your case that this wasn't self-employment. When you file, include a simple statement explaining that the amount was incorrectly reported on a 1099-NEC when it should have been classified as a student research stipend, not subject to self-employment tax. Reference that acceptance letter in your statement.

This is actually good advice. I had a similar issue with a teaching stipend and when I contacted the university accounting office, they agreed it was miscoded and issued a corrected form. Saved me tons of hassle.

Did you have to fill out the full Form 2210 with all the calculations, or did TurboTax handle that for you? That form looks super complicated and I'm wondering if I need to pay extra for that feature.

TurboTax handled all the calculations automatically for me. I didn't have to manually fill out anything on Form 2210. The software asked about my estimated payments throughout the year, and when it detected that I had missed one, it just did the math in the background. You shouldn't need to pay extra for this feature - it's part of their standard tax return preparation. The form is definitely complicated if you try to do it manually, but that's the beauty of tax software. Just make sure you accurately enter the dates and amounts of the estimated payments you did make.

You'll still need to complete Form 2210 when you file. Making a payment now as "balance due" helps reduce further interest from accruing, but it doesn't eliminate the need to calculate the penalty for the period the payment was late. Most tax software will handle this calculation automatically if you enter all your payment information correctly. If you're filing by paper, you'll need to complete the form yourself. The IRS can also calculate the penalty for you if you don't include the form, but they may not apply all exceptions or calculate it as favorably as you might.

I'm in the same boat as you and just made my payment using "balance due" yesterday. My tax guy told me that we'll handle the Form 2210 when filing, and that the penalty won't be huge since my first three estimated payments were made on time. I'll report back after filing to let you know how it went!