A stereocontrolled halo-Prins/halo-Nazarov cyclization protocol is reported, where chiral information from a secondary alcohol is relayed through several intermediates yielding halocyclopentene products diastereoselectively. An enantiopure product is obtained when a nonracemic secondary alcohol is used. Experimental and computational studies are described, enabling the design and synthesis of systems that ionize and cyclize with >95% chirality transfer through a mechanism involving the creation and preservation of transient helical chirality in a pentadienyl cation intermediate. First, a diastereoselective alkynyl Prins cyclization is executed to synthesize a conformationally distorted dihydropyran intermediate with a curved backbone and high reactivity. This chiral precursor adopts a specific helical alignment early in the subsequent cationic ionization/halo-Nazarov cyclization process, dictating the direction of conrotation in the electrocyclization. Notably, despite the ablation of an sp3 stereogenic center during ionization, the low halo-Nazarov barrier enables efficient capture of a cationic intermediate with dynamic conformational chirality. The ionization and electrocyclization thus occur with "memory of chirality".