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In this situation, you sell your ESPP shares more than one year after purchasing them, but less than two years after the offering date. This is a disqualifying disposition because you sold the stock less than two years after the offering (grant) date.
How is the $25,000 limit calculated? The basic rule is that each employee cannot purchase more than $25,000 per year, valued using the fair market value on the date he/she enrolled in the current offering.
Disadvantages of Employee Stock Purchase Plans Ensuring the ESPP follows security and tax law guidelines can be challenging. A large amount of HR functions goes into administering the stock purchase plan. There are legal, tax, and administrative issues that go into setting up the plan.
Employees who elect to participate in a qualified ESPP are typically able to take advantage of some tax benefits, as the discount is not recognized as taxable income until the stock is sold. When you sell the stock, the discount you received when you bought it may be taxable as income.
The ESOP vs 401K Plan With a 401(k), the employer's contributions are tax-deferred, meaning that the money is taken out of each paycheck before taxes, and those wages are not taxed until withdrawal. Whereas with an ESOP, employees also do not pay taxes on the shares in their account until distribution.
The Bottom Line. Employee stock options can be a valuable part of your compensation package, especially if you work for a company whose stock has been soaring of late. In order to take full advantage, make sure you exercise your rights before they expire.
An employee stock purchase plan (or ESPP) can be a very valuable benefit. In general, if your employer offers an ESPP, we think you should participate at the level you can comfortably afford and then sell the shares as soon as you can.