In summary, we have reported a light-mediated oxyalkynylation of the C-C bond of arylcyclopropanes via the direct photoactivation of aryl-EBX reagents with visible light. In contrast to previous works, neither photocatalysts nor additive were needed. In addition, we discovered a complete switch of the reaction outcome from C-C to C-H alkynylation when using aryl cyclopropanes bearing two ortho substituents on the benzene ring. We tentatively attributed this effect to the conformational constrains induced by the aryl ring, and we think this result will pave the way for the development of new selective transformations of cyclopropanes.