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Instead of cash contributions, consider making an in-kind contribution of appreciated stock as a direct transfer from your brokerage account to the charity. The market value of the stock on the date of transfer is the value of the itemized deduction. Neither you nor the qualified charity pay the tax on the capital gain. If the stock is a long-term keeper, then you can use the cash that you were going to give the charity (in lieu of the stock) to acquire additional shares of the same stock, this technique is an effective way to raise the cost basis of your portfolio which will lower future capital gains taxes. This strategy pairs well with the bunching of charitable donations discussed Here.

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