High voltage transmission line design requires careful insulator selection to ensure good operational performance. This paper reports on the in-situ measurements of leakage current (LC) on composite and glass insulators of the Cahora Bassa high voltage direct current (HVDC) transmission line in South Africa over a 6month period. The influence of temperature, humidity, dew, rain and the HVDC line's voltage and current on LC are investigated. The results show that the composite and glass insulator LC behaviour is similar, except in cases of high humidity or rain. At the commencement of rainfall and humidity (>90%), elevated LC levels are observed on glass insulators, while composite insulators demonstrate lower LC levels under these conditions. Under nominal weather conditions of no rain and low humidity, the LC measurements exhibit an almost square-wave behaviour with LC switching between lower (≈20 µA) and higher values (≈60 µA) with relatively short transitions on a daily basis. This phenomenon can be ascribed to condensation on the insulators, which is a primary determinant of the LC levels on contaminated insulators. The line current and voltage fluctuations do not influence the LC level.