A simple Lewis acid-mediated route for the synthesis of alkenyl halides are described under microwave-assisted conditions. The reaction proceeds through the condensation between secondary alcohols and terminal acetylenes and regioselective hydrohalogenation across the triple bond in the presence of simple and commercially available zinc halides. Unlike earlier reports, this methodology is successfully exemplified with three halide sources. As a result, a diverse range of alkenyl halide products has been accomplished. Further, indenes were obtained as the end products when tertiary alcohols and arylacetylenes were used, wherein the Thorpe–Ingold and electronic effects, would be dominant. Furthermore, when an electron-rich arylacetylene was employed, the reaction directed to yield carbonyl products. © 2021 Wiley-VCH GmbH