A silver-catalyzed intramolecular denitrogenative annulation of pyridotriazole with alkene was reported to achieve the challenging carbene insertion into the vinylic C(sp2)-H bond. This protocol has enabled the construction of functionalized 1H-indenes with high efficiency and excellent functional group tolerance. Experimental and computational studies suggest a stepwise mechanism involving a water-promoted hydrogen atom transfer with the aid of a silver catalyst.