By inventing strategies to forge C-P bonds, chemists provide entrance to organophosphorous architectures for versatile applications in medicine and catalysis. 1 Among these architectures, the cyclopropyl phosphine motif garners attention because of its distinctive steric and electronic attributes. For example, a cyclic analogue of fosmidomycin shows enhanced antibiotic activity against E. coli, presumably due to restricted rotation. In the realm of catalysis, Takasago's cyclopropyl phosphine ligand, cBRIDP outperforms its vBRIDP in Suzuki-Miyaura cross coupling. Considering ways to construct cyclopropyl phosphines, we focused on hydrophosphination: the direct addition of a P-H bond across a C-C multiple bond. Hydrophosphination represents an attractive and atom-economical platform for controlled synthesis of molecules with stereogenic carbon and/or phosphorous atoms. While progress has been made, stereoselective methods remain rare beyond use of alkynes, 7 oxa-bicycles, 8 and Michael acceptors. 9 Driven by strain release, 10 cyclopropenes show high reactivity, and the hydrofunctionalization of cyclopropenes has enabled a direct access to a diverse range of enantiomerically enriched rings. In this report, we disclose enantioselective Cu-catalyzed hydrophosphination to access a range of cyclopropylphosphines at ambient temperature. A unique Cu-phosphido mechanism is supported by both experimental and theoretical studies. We provide insights into ligand trends for selectivity using buried volume analysis.