Charitable Stock Donation vs Cash 2027 Calculator
Compare the after-tax value of donating appreciated long-term stock vs equivalent cash to a public charity in 2027.
Why Donating Appreciated Stock Wins
When you donate appreciated long-term stock (held >1 year) to a qualified 501(c)(3) public charity, you (1) deduct the FULL fair market value, NOT your basis, AND (2) avoid the capital gain tax you would have owed if you sold the stock first. This double tax benefit makes appreciated stock the most tax-efficient form of giving — yet most donors still use cash. Source: IRC §170(e). Last updated: May 2026.
The Two-Layer Tax Win
Layer 1: deduction value. $30K stock donation × 32% marginal = $9,600 saved (same as $30K cash). Layer 2: avoided gain. $20K gain × (15% LTCG + 3.8% NIIT) = $3,760 saved. Total stock benefit = $13,360 vs cash benefit = $9,600. The stock wins by $3,760 — entirely from avoiding capital gains.
Holding Period Requirement
Stock must be held MORE THAN 1 YEAR to deduct at FMV. Short-term holdings get deduction at LESSER of FMV or basis — eliminating the FMV advantage. If you have appreciated stock held just under a year, wait until day 366 before donating. The IRS counts trade date to trade date, not settlement to settlement.
What If You Love the Stock?
Easy fix: donate appreciated shares, then use cash to buy new shares immediately. You end up holding the same position with a STEPPED-UP BASIS equal to your purchase price — essentially resetting unrealized gain to zero. This 'tax-loss-harvest in reverse' is a major reason high earners use Donor-Advised Funds.