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The date when the seller receives the sales price (minus the broker's commission) and the buyer receives the shares. The notation T+2 refers to the obligation in the brokerage business to settle securities trades by the second business day after the trade date. This means that with a cashless exercise, or with a sale at restricted stock/RSU vesting or ESPP purchase, the cash will not show up in your account until at least two days after the transaction.
Your taxable income and your company's withholding obligation are based on the market price when the stock underlying the grant is considered transferred to you under the tax laws, not on the settlement date. (See IRS Generic Legal Advice Memorandum (GLAM) No. AM 2020-004.) It does not matter if the stock price has changed since exercise, purchase, or vesting.
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