A novel cycloaddition strategy for the synthesis of fused, multifunctionalized salicylaldehydes and salicylketones by a one‐pot, three‐step cascade hexadehydro‐Diels–Alder (HDDA) reaction of tetraynes followed by an intermolecular aldehyde/ketone reaction and hydroxylation is presented. Target compounds underwent intramolecular cyclization to produce bicyclic salicylaldehydes. The overall transformation involves the formation of four new C−C bonds and one new caryl−O bond by both intramolecular and intermolecular reactions. The reaction is easy to perform, proceeds under mild conditions and exhibits excellent regioselectivity. Water, a simple and readily available reagent, was employed as the OH source. For more information see the Full Paper by Y. M. Hu, S. Wang et al. on page 4065 ff.