ESPP Sale Planner

Compare selling a qualified employee stock purchase plan lot now with holding it, including ordinary income and capital gain.

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Qualified ESPP lot

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Sale alternatives

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Federal tax assumptions

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Lot basis

Purchase price per share$85.00
Total purchase cost$8,500.00

First qualifying sale date: 2027-01-02. Both holding periods must be satisfied.

Both tax alternatives use 2026 federal rules, the standard deduction, and the entered wages. A later share price is an assumption; the comparison does not price the risk of holding employer stock.

Sell now

Disqualifying disposition · Long-term capital treatment

Ordinary income$3,500.00
Capital gain / loss$500.00
Adjusted basis$12,000.00
Incremental federal tax$879.00
After-tax proceeds$11,621.00
Capital loss without modeled tax benefit$0.00

Sell later

Qualifying disposition · Long-term capital treatment

Ordinary income$1,500.00
Capital gain / loss$3,000.00
Adjusted basis$10,000.00
Incremental federal tax$780.00
After-tax proceeds$12,220.00
Capital loss without modeled tax benefit$0.00
Later-sale after-tax difference$599.00
How it works›

Qualifying disposition. After both the two-year grant period and one-year transfer period, ordinary income is the lesser of the grant-date discount and the actual gain, floored at zero. If the option price was not fixed at grant, use the price as if exercised at grant (Form 3922 box 8). Remaining gain is long-term capital gain.IRS Publication 525Form 3922 instructions

Disqualifying disposition. Ordinary income is the purchase-date market value less the purchase price, even when the shares later sell at a loss. Add that income to basis before measuring capital gain or loss. A disqualifying sale can still have long-term capital treatment when only the two-year grant test fails.IRS Publication 525

Scope and loss treatment. Assumes an already eligible IRC 423 lot and valid employment/plan limits; it does not determine annual purchase eligibility. Other investments, itemized deductions, state/local taxes and fees are excluded. Capital losses are displayed without assuming a current offset or refund. Statutory ESPP wages have no modeled payroll withholding. Holding can change the share price as well as tax treatment.IRS Publication 525