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Investors & landlords
You wouldn't because your W-2 should not reflect the amount of any gain you had from the sale of your ESPP shares. Rather, it should reflect the discount you received when you purchased the shares. The discount is the difference between the exercise price (the price you paid for the shares) and the market price on the exercise date. That discount--which is usually 15% for many firms, but it could be less depending on the plan--is a form of compensation, and therefore, firms are required to include the discount amount on the W-2. If it's not there, then employees need to report it. If you have some doubts as to whether your W-2 includes the discount, you might consider verifying with your firm that it does.
Your 1099-B, or similar document, should reflect whether you had a gain or loss on the sale of your ESPP shares. It is possible that your cost basis may not be accurate on your 1099-B. The cost basis for your shares should be the market price on the date you purchased your shares--box 4 on Form 3922--multiplied by the number of shares purchased. Your box 14 amount could pertain to family medical leave, and if it does, it is not relevant to your ESPP purchase/sale.
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