The Daily Insight
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How do I report sale of ESPP shares?

So you must report $225 on line 7 on the Form 1040 as “ESPP Ordinary Income.” You must also report the sale of your stock on Schedule D, Part II as a long-term sale.

Should I sell my ESPP shares right away?

If you are risk-averse, you might consider selling your ESPP shares right away so you don’t have overexposure in one stock, particularly that of your own employer. However, selling too early may have unfavorable tax consequences compared to holding the stock for a longer period of time.

Can you keep ESPP shares after leaving company?

If I leave the company, what happens to the money that has been deducted from my paycheck to purchase ESPP shares? You will continue to own stock purchased for you during your employment, but your eligibility for participation in the plan ends.

Is ESPP before or after tax?

An ESPP typically works this way: You contribute to the ESPP from 1% to 10% of your salary. The contribution is taken out from your paycheck. This is calculated on pre-tax salary but taken after tax (unlike 401k, no tax deduction on ESPP contributions).

Should you max out ESPP?

In general, it’s a good idea to max out your other retirement accounts before contributing to an ESPP. The tax breaks offered by those accounts are generally better than the discount offered by an ESPP.

When to sell ESPP stock for tax purposes?

If the ESPP securities are sold either within two years of the offering date or within a year of the purchase date, the sale is considered a disqualified disposition. A qualified disposition may result in preferential tax treatment. The W-2.

When is a sale of ESPP a qualified disposition?

A sale of ESPP securities is considered to be a qualified disposition when the stock is sold over two years after the offering date and over a year after the purchase date. If the ESPP securities are sold either within two years of the offering date or within a year of the purchase date, the sale is considered a disqualified disposition.

How is the purchase price determined for ESPPs?

Under most plans, the purchase price is a discounted price, generally up to 15%. Some plans include a “look-back” feature, which compares the share price at the beginning and end of the offering period and uses the lower price to determine the purchase price. ESPPs can be qualified or nonqualified.

When to sell employee stock purchase plan shares?

With a qualifying disposition (meaning you held your ESPP shares for more than two years from the offering date, and one year from your purchase date) you are able to report more of your profit as a capital gain rather than as earned income.