Frequently Asked Questions
How does the ESPP lookback work?
A lookback discounts the purchase off the lower of the offering-date price and the purchase-date price, which increases your return when the stock has risen during the offering period.
What is a qualifying versus disqualifying disposition?
A qualifying sale, held more than one year from purchase and two years from the offering date, gets favorable tax treatment on part of the gain. A disqualifying sale taxes more of the discount as ordinary income.
Should I sell ESPP shares immediately?
Selling right away locks in the discount but forfeits qualifying treatment, while holding adds tax benefits and concentration risk. The right choice depends on your taxes and risk tolerance.
Is this investment advice?
No. It is a general estimate and is not investment, tax, or financial advice. Review your specific plan and tax situation with a professional.
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Investment Disclaimer: Estimates only. Not investment advice.
This calculator provides estimates for educational purposes only and is not investment advice. Past performance does not guarantee future results. Consult with a qualified financial advisor before making investment decisions. All investments carry risk, including potential loss of principal.