Why should I donate appreciated shares to charity instead of writing a check?

Donating stock you've held more than a year that has gained value is one of the most tax-efficient ways to give. You get a charitable deduction for the full fair-market value of the shares, and you completely avoid the capital gains tax you'd owe if you sold them first. So a $10,000 stock position you bought for $4,000 lets you deduct $10,000 and skip tax on the $6,000 gain – a double benefit. Compare that to selling, paying tax on the gain, and donating the smaller after-tax amount. A donor-advised fund makes this easy: contribute appreciated shares, take the deduction now, and grant to charities over time. To claim the deduction you must itemize, and gifts of appreciated securities are deductible up to 30% of your adjusted gross income, with a five-year carryforward for the excess.