Direct answer
Family stock moves follow the same audit trail: wash-sale windows, spouse accounts, gifts, and 10b5-1 plans bind post-exit. The plan is built from basis, dates, and records, not memory. Executive packages add the 280G line in the 280G trades guide , transfer clocks in the transfer vesting guide , and comp records in the records guide .
Updated November 9, 2026 · Reviewed against IRS — tax guidance
Family stock moves follow the same audit trail: wash-sale windows, spouse accounts, gifts, and 10b5-1 plans bind post-exit. The plan is built from basis, dates, and records, not memory.
The Family Lines
- Wash sales: 30-day repurchase disallows losses across accounts, including spouse and retirement; the basis carries forward (see the wash-sale guide).
- Gifts & estate: gapped basis, gift lines, and estate valuation; the 409A trail is in the 409A guide, and the 1099-B audit in the 1099-B guide.
- 10b5-1 & windows: trading plans survive separation, insider rules follow SEC lines (sec.gov); the exercise clock is in the exercise guide and AMT in the AMT guide.
Executive packages add the 280G line in the 280G trades guide, transfer clocks in the transfer vesting guide, and 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.
Wash sales are created across accounts, not inside one
A loss is disallowed when substantially identical shares are bought within the wash-sale window around the sale, and the window reaches other accounts, including a spouse’s account and an IRA. That is how a rebalance in one account destroys a loss harvested in another.
- Check every account before selling for a loss: your brokerage, spouse accounts, retirement accounts, and any automatic investment plan or dividend reinvestment.
- Watch option exercises and RSU vests: acquiring shares in the same name can be the purchase that disallows a prior sale.
- Disallowed losses are not lost: the basis and holding period adjustments carry into the replacement shares, so the record has to follow the position.
- Keep lot records: purchase dates and prices per lot, since a broker’s 1099-B reporting is not always your actual cost.
Ask your CPA to review lots across accounts before a loss-harvest week. The equity vesting entry explains how RSU and option basis get set, which is where family-level mistakes start.
Gifting shares: the four records to keep
A gift is a tax event with paperwork consequences, and the recipient’s outcome depends on records you control today:
- Original purchase date and price for the lot being gifted, plus any adjustments.
- The gift date and the fair market value on that date, which drives any reporting question.
- The holding period carryover, since the recipient inherits your clock, which changes short versus long gain.
- A written statement of who now owns the shares, especially where a minor’s account or a custodial account is involved.
Confirm the current federal exemption, gift-reporting thresholds, and filing form with the IRS guidance and your CPA rather than with remembered numbers; these figures change. Then keep the gift record in the same family folder as the W-2 and the 1099-B statements for the year, so a later question has one answer.
Trading plans and separation rules
Family stock decisions get complicated at exit because plan rules and insider rules survive the last day:
- A written trading plan can bind after separation. Ask the stock administrator in writing whether the plan continues, when it can be modified, and what happens on your separation date.
- Do not adopt or change a plan while aware of material nonpublic information. That is the fact pattern regulators examine, and it is a counsel question, not a paperwork habit.
- Insider restrictions can outlast employment, so confirm in writing whether any window or blackout applies to you as a former executive.
- Exercise windows still run. Options expire on the plan’s post-termination deadline regardless of a trading plan; the vesting calculator prints your dates.
- Executive packages add parachute math: read the 280G entry before a closing agreement signs.
Keep the administrator’s written answers, the grant list, and the plan documents in one folder, and calendar the deadlines in the application tracker where a job-search week cannot bury them.
| Move | The trap | Record to keep |
|---|
| Sell for a loss | A purchase in a spouse or retirement account disallows it | Lot lists across every account, dated |
|---|
| Gift appreciated shares | Carryover basis surprises the recipient | Original cost, purchase date, gift date, market value |
|---|
| Exercise or vest then sell | A wash or a blackout window appears | Exercise confirmations and window rules in writing |
|---|
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 hiring references non competes guide hub. Rules move, and those pages carry the current text.
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Frequently Asked Questions
- Can a wash sale be created in my spouse's account?
- Yes. Purchases of substantially identical shares in a spouse’s account, or in an IRA, can disallow a loss realized in your own account. Review lots across every household account before harvesting losses, with your CPA.
- What basis do gifted shares carry?
- Generally your original basis and holding period carry over to the recipient, which can create unexpected tax on a later sale. Keep the purchase date, cost, adjustments, gift date, and market value on the gift date in one written record.
- Does a trading plan continue after I leave?
- It can bind after separation, depending on the plan terms and the company’s rules. Ask the stock administrator in writing whether the plan continues, what happens on your separation date, and whether any restriction still applies to former insiders.
- Do RSU vests count as purchases for wash-sale rules?
- Acquisitions of the same shares can matter, so a vest or an option exercise near a loss sale is worth reviewing. Ask your CPA to check the dates and lots across accounts before you sell, and keep the vest records with the 1099-B.
Family transfers, the exercise window, and the gift and estate lines are plan and IRS rules, and the state estate and inheritance thresholds are state rules graded in this build from reported sources. Confirm the exercise window with the plan administrator, confirm the state threshold with the state tax agency named on the state rule pages, and keep the grant date, the valuation, and the transfer paperwork in one dated file. Keep the transfer dates, the exercise window, and the filing window in the application tracker so the year split has a dated source.
Sources (official record — verify before filing)
IRS — tax guidance