While you have likely heard about tax-loss selling, crystallizing a capital loss to shelter capital gains realized in the prior three calendar years, tax-gain donating involves crystallizing those winning stocks or mutual funds by donating them “in-kind” to a registered charity. Donations of publicly traded shares, mutual funds or segregated funds to a registered charity not only get you a tax receipt equal to the fair market value of the securities or funds being donated, but also allow you to avoid paying capital gains tax on any accrued gain on the shares or funds donated. Even if you want to hold on to that winning stock in the hope of enjoying further capital appreciation, you can simply take the funds that you were going to use for the donation and buy back the securities you just donated “in-kind.” That way, you get the donation tax receipt, pay no tax on the capital gain to date and bump up your adjusted cost base of the security repurchased back up to fair market value, reducing your ultimate tax bill on a future sale.