"Why Make Gifts of Appreciated Stock? By giving appreciated stock to a charity, you get a deduction for the full value of the stock. If you sell the stock and donate the proceeds, you will owe tax on the capital gain, and pay applicable commissions. The capital gain will be added to your adjusted gross income (AGI): If AGI gets too high; you may trigger the tax benefit phase-out levels for personal exemptions, itemized deductions, IRA deductibility, and Roth IRA eligibility. High AGI may also trigger the 3.8% net investment income tax and higher premiums for Medicare Parts B and D."