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An employee stock purchase plan (ESPP) is a benefit that allows people to buy stock in the company they work for at a discounted price. Large companies or public corporations sometimes offer these plans, and they use the sum of their total employee contributions to make a large investment in the company.
When may I sell my stock in an ESPP? A. Employees can generally sell shares purchased through the employee stock purchase plan at any time. However, if the shares were purchased under a Section 423 plan, the tax consequences will be different depending on how long you have held the shares.
When you buy stock under an employee stock purchase plan (ESPP), the income isnt taxable at the time you buy it. Youll recognize the income and pay tax on it when you sell the stock. When you sell the stock, the income can be either ordinary or capital gain.
What is a qualified section 423 Plan? A. A qualified 423 employee stock purchase plan allows employees under U.S. tax law to purchase stock at a discount from fair market value without any taxes owed on the discount at the time of purchase.
You report this amount as compensation income on your 2021 Form 1040. You show the sale of the stock on your 2021 Schedule D. Its considered long-term because more than one year passed from the date acquired (January 2, 2020) to the date of sale (January 20, 2021).

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There are two classifications of sales for qualified ESPPs: qualifying and non-qualifying dispositions. To be eligible for a qualifying disposition, you can only sell your shares after more than two years have passed since the grant date (start of the offering period) and youve held the shares for more than one year.
An ESPP allows you to purchase company stock at a discounted price, often between 5-15% off the fair market value. For example, if the fair market value on the applicable date is $10 per share, and your plan offers a 15% discount, you can purchase those shares for $8.50 per share.
It usually takes 2-3 weeks for the trade to appear after the purchase date. Our plan requires a minimum 3-month holding period, so your plan may be different.
If youd like to make a riskless profit from your discounted purchase, you can sell the company stock immediately after purchasing. If youre getting a 10% discount, then you can generate a riskless 10% profit from your employee stock purchase plan. This is one of the best benefits of an employee stock purchase plan.
An ESPP can either be a qualified (Section 423) or non-qualified plan, and the type of plan youre able to participate in will typically be completely out of your control.

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