Chlorination of 1,2,3,4-tetracyclohexyl-cyclo-tetraphosphine (2) by PhICl2 or PCl5 in the presence of Me3SiOTf or GaCl3 provides a stepwise approach to salts of the first cyc/o-phosphino-chlorophosphonium cations [Cy4P4Cl](+) ([19](+)) and [Cy4P4Cl2](2+) ([20](2+)). The analogous iodo derivative [Cy4P4I](+) ([17](+)) is obtained as the tetraiodogallate salt from reaction of 2 with 12 in the presence of Gala. Reactions of the dication [20](2+) with PMe3 or dmpe effect a dissociation of the cyclic framework resulting in the formation of salts containing [Me3PPCyPCyPMe3](2+) ([27](2+)), [dmpeCyP](2+) ([29](2+)), and [dmpeCyPCyP](2+) ([30](2+)), respectively. The new cations represent phosphine complexes of the [PCy](2+) and [P2Cy2](2+) cationic fragments from [20](2+), demonstrating the coordinate nature of the phosphinophosphonium bonds in cyclo-phosphinohalophosphonium cations. The compounds have been characterized by NMR spectroscopy, single crystal X-ray crystallography, and Raman spectroscopy.