This paper describes the design, fabrication, commissioning and use of a CALibration source Insertion System (CALIS) in the DarkSide-50 direct dark matter search experiment. CALIS deploys radioactive sources into the liquid scintillator veto to characterize the detector response and detection efficiency of the DarkSide-50 Liquid Argon Time Projection Chamber, and the surrounding 30 t organic liquid scintillator neutron veto. It was commissioned in September 2014 and has been used successfully in several gamma and neutron source campaigns since then. A description of the hardware and an excerpt of calibration analysis results are given below.