Model ESPP tax basics: purchase discount, holding periods, and what may show up as wages vs capital gain.
Rates and rules change. Check the tax year and last-reviewed date on each page, then confirm against IRS or state guidance before you file.
Spot an outdated rate or date?
We update when we can, but we miss things. Send a link to the official source if you have one.
Email usStart here
Planning estimate
Educational estimate only. Whether your ESPP sale is qualifying or disqualifying depends on your plan and holding-period dates, which change the tax treatment. Confirm with your plan documents and a tax professional.
We do not pre-fill personal financial values. Estimates appear only after you enter your own numbers.
Enter your details to estimate
Add your equity, income, state, and withholding details to see an educational estimate. No personal financial values are pre-filled.
Start with the fields below.
Enter your own numbers below. This is an estimate, not a filing position.
Depends on how long you held from the offering and purchase dates.
Required to estimate
Discounted price you actually paid.
Required to estimate
Required to estimate
Used for qualifying dispositions with a lookback.
Required to estimate
Your ESPP discount, often a set plan percentage.
Results will appear here once you enter the required details on the left.
Options and RSUs follow different tax paths. know which events create wage income vs capital gain.
1099-B for RSUs often shows low or zero basis. that does not mean your true basis is zero.
Basis adjustments connect vest wage income to later sales. document FMV from vest records.
RSUs are usually taxed as wages when they vest, not when the grant is signed. This guide walks through the timeline in plain terms.
ESPPs typically let you buy at a discount to market price.
Whether a sale is 'qualifying' or 'disqualifying' depends on holding periods tied to the offering and purchase dates.
Part of the benefit is usually ; the rest is or loss when you sell.
Some of the ordinary-income portion may already appear on your .
Common mistake
Example scenario (hypothetical)
Illustration only, not your tax situation.
Options and RSUs follow different tax paths. know which events create wage income vs capital gain.
ISOs and NSOs are taxed differently. the exercise and sale timeline drives most of the difference.
Reporting RSUs means connecting W-2 wage income to brokerage 1099-B sales. this guide maps the flow.
For learning, not filing
Grants, employers, and states all differ. Use your own documents and a qualified tax professional before you make decisions from this guide.