Unusual Pd deactivation and inhibition pathways were observed in a C-N coupling system. Irreversible catalyst deactivation involved C-H insertion of Pd into BippyPhos leading to an off-cycle palladaphosphacyclobutene. Product inhibition led to deactivated Pd but released ligand in the process, allowing it to react with additional Pd precursor to re-enter the catalytic cycle. In situ recycling of the ligand allowed for an input L/Pd ratio of ≪1 with no impact on reaction kinetics.