Direct answer
Wash-sale rules bite post-exit: selling shares at a loss and repurchasing within 30 days disallows the loss, and RSU sales stack with new grants. The 1099-B trail is the audit file; the plan is built from basis, not memory. Executive packages add the 280G line in the 280G trades guide , the transfer clocks in the transfer vesting guide , and the comp records in the records guide .
Updated November 9, 2026 · Reviewed against IRS — tax guidance
Wash-sale rules bite post-exit: selling shares at a loss and repurchasing within 30 days disallows the loss, and RSU sales stack with new grants. The 1099-B trail is the audit file; the plan is built from basis, not memory.
The Rule Set
- 30-day window: repurchase (including in retirement accounts) disallows the loss; the adjusted basis carries the disallowed loss forward.
- RSU sales: vesting = income at FMV; sales after vesting run capital gains/losses on the spread. The 1099-B form matches the brokerage trail (see the 1099-B guide and the 409A guide).
- Post-exit windows: trading windows survive separation, 10b5-1 plans bind, and insider sales follow SEC lines (sec.gov). The exercise clock is in the exercise guide, and the AMT math in the AMT guide.
Executive packages add the 280G line in the 280G trades guide, the transfer clocks in the transfer vesting guide, and the comp records in the records guide.
Put the rule into action
Write the letter with the free Severance Package Negotiation Letter generator. The state pages carry the local payout and notice windows, and the application tracker keeps the follow-up date in writing.
Running The 30-Day Calendar Before You Sell
Direct answer: a wash sale happens when you sell a security at a loss and buy a substantially identical one within the window around the sale, and the disallowed loss is added to the basis of the replacement shares rather than disappearing. The window is the 30-day period described on this site, counting both sides of the sale, and repurchases inside retirement accounts count too. Plan the calendar before you trade, especially after an exit when RSUs vest on a schedule you do not control.
- List every purchase and sale of the same security for the surrounding months, including automatic RSU vestings and any 401(k) fund that holds employer stock.
- Mark each loss sale and ask whether anything substantially identical was bought within the window. Options that result in acquiring the stock can matter; confirm with your tax professional.
- If a loss is disallowed, record the added basis. The loss is deferred into the replacement lot, not lost forever, and it is easy to forget by the time you sell again.
- Do not chase the loss with a different security merely to dodge the rule; substantially identical questions are fact-specific and brokerage forms are not always right.
- Check the brokerage's wash-sale reporting against your own ledger. Brokers report what they can see, which often misses cross-account and retirement-account purchases.
RSU Sales: Two Taxes, Two Dates, One Lot
Exit-year equity mistakes come from treating a vest and a sale as one event. They are two different calculations with different dates.
- Vesting is wage income. Restricted units report income at fair market value when they vest, withheld or not, and that line belongs on the W-2 for the year of vesting. See the equity vesting entry.
- Selling is a capital transaction. Gain or loss runs from your basis, which is usually the value already taxed at vesting, to the sale price, and the holding period decides short or long treatment.
- Missing basis is the common error. When the broker reports zero basis for shares you received as compensation, the gain is overstated. Correct it with your vest records.
- Do not rebuy the same stock inside the window after a loss sale, including inside a retirement account rollover. Run the dates in the Vesting & Cliff Calculator for vest timing and keep the trade list separately.
- Keep the 1099-B trail. The brokerage form is the audit file, and a corrected statement is easier to obtain in the same year as the sale.
Post-Exit Trading Windows And Plan Rules
Leaving does not always free you to sell, and the paperwork decides when you can.
- Trading windows. Some companies keep former employees inside blackout windows tied to reporting cycles. Ask which rules still apply to you after separation.
- Rule 10b5-1 plans. A pre-set sale plan binds you; if one exists, get the schedule and the terms in writing rather than guessing your own exit date.
- Insider status can persist. Sales by people with board seats or large holdings follow SEC rules; see sec.gov for the current requirements rather than advice from a colleague.
- Option exercise clocks are separate. A post-termination exercise window sets your deadline, and incentive options carry alternative-minimum-tax questions; read the plan document, not the org chart.
- Executive packages add a tax layer. A change-of-control payout can carry parachute calculations; see the 280G entry and put questions in writing before you sell anything.
Ask your employer for the grant statements, vest dates, and the plan documents before access ends, and send the ask with the Severance Package Negotiation Letter generator if you are still negotiating the package.
| Event | Tax Line It Creates | What To Check |
|---|
| RSU vesting | Wage income at fair market value | W-2 line and the withholding actually taken |
|---|
| Sale of vested shares | Capital gain or loss from basis | Basis reported by the broker versus your records |
|---|
| Repurchase inside the window | Loss disallowed and added to basis | Cross-account and retirement-account buys |
|---|
| Option exercise | Spread treatment and possible AMT | Plan window and the grant type |
|---|
| Blackout or 10b5-1 sale | Timing, not tax | Which post-exit rules still bind you |
|---|
Before you rely on a date or an amount on this page, check it against the California job exit rules page and the New York job exit rules page, along with the 401(k) Vesting Schedule definition and the equity tax trails guide hub. Rules move, and those pages carry the current text.
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Frequently Asked Questions
- When does a wash sale disallow my stock loss?
- When you sell at a loss and buy a substantially identical security within the window around that sale, including inside a retirement account. The loss is not destroyed: it is added to the basis of the replacement shares, so record it or you will lose it later.
- Why is the basis on my RSU sale reported as zero?
- Because the broker often does not know the value already taxed as wage income when the units vested. Correct the basis using your vest records; the income was reported on the W-2 in the vesting year, and the sale is a separate capital transaction.
- Can I still sell company stock after I leave?
- Only under the rules that still apply to you. Some companies keep former employees inside blackout windows, pre-set sale plans continue to bind, and insider rules can persist. Ask which rules apply and get the schedule in writing before you place an order.
- Do automatic RSU vestings trigger a wash sale?
- They can, because a vesting is an acquisition of the same security. If you sell at a loss near a vest date, check the window on both sides of the sale and keep the ledger; brokerage forms frequently miss acquisitions you did not initiate.
Wash-sale windows are brokerage and IRS rules tracked across accounts, not state law. Confirm the basis lines against the 1099-B trail, keep the brokerage statements in the same archive as the W-2, and confirm the wage-side windows — final pay, PTO payout, and the claim deadline — with the state agency named on the state rule pages before you build a claim that touches equity income. Keep the wage-claim record beside the brokerage trail: the final pay check demand generator puts the state window on paper.
Sources (official record — verify before filing)
IRS — tax guidance