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.

Can you claim any penalties or extra interest if your refund was delayed because of an IRS error? My refund was delayed for 6 months last year because they incorrectly flagged my return!

Unfortunately, no. The standard interest they pay for delayed refunds is the only compensation you'll receive, regardless of why the delay occurred. The IRS pays interest on delayed refunds if they're issued more than 45 days after the return due date or the date you filed, whichever is later. Even if the delay was caused by an IRS error, there's no additional penalty or interest payment beyond what they automatically calculate. It's frustrating, but the 1099-INT interest payment is all you'll get. The interest rate they pay is set by law and adjusts quarterly based on federal short-term rates.

lol welcome to government efficiency! they literally could just adjust your taxes automatically but instead they send you a form to tell you to tell them about money they paid you. peak bureaucracy right there

Thanks, that makes sense in a completely nonsensical way lol. Government gonna government I guess. Just seems like such a waste of paper and time to send us forms about information they already have!

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.