Navigating 423 Employee Stock Sales and Taxes

Dr Friday Tax Tips - One Minute Moment
Dr. Friday Tax Tips
Navigating 423 Employee Stock Sales and Taxes

In this episode, Dr. Friday delves into the complexities of reporting sales from a 423 employee stock purchase. She highlights the potential pitfalls of Schedule D and AMT tax implications, and the common misconception of being taxed twice. If you’ve sold stock from an employee purchase plan, this is a must-listen.


G’day, I’m Dr. Friday, president of Dr. Friday’s tax and financial firm. To get more info go to This is a one-minute moment.

I purchased stock for my employer under a 423 employee stock purchase and received a 1099-B for selling it. How do I report this? And this is very important because you’re going to have two situations. You’re going to have a schedule D where you report the gain, but you may also have an AMT tax that you have to report the sale with. Sometimes that can kick you into a whole different tax bracket and understanding the difference because a lot of people say, wait they already took the taxes out of my W-2, I shouldn’t have to pay it twice. You might want to revisit that thought. It isn’t tax twice, but there is a difference. Give us a call 615-367-0819.

You can catch the Dr. Friday Call-In Show live every Saturday afternoon from two to three p.m. right here on 99.7 WTN.