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Rubric Financial

Tax

Employee Stock Purchase Plan (ESPP)

A program letting employees buy company stock at a discount, often with a lookback feature.

ESPPs typically offer a 10–15% discount on company stock, often with a lookback that uses the lower of the offering-date or purchase-date price.

Tax treatment depends on holding period. Qualifying disposition (held 1 year past purchase AND 2 years past grant): the discount is ordinary income, the rest is long-term capital gain. Disqualifying disposition: the entire discount at purchase is ordinary income.

Common pitfalls

  • 1099-B forms typically show only the basis you paid — leading to double taxation if you don't adjust for the ordinary income piece
  • Forgetting that ESPP discount is W-2 income reportable to the employer

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