Boundary lubricated journal bearings are found in various applications involving oscillatory sliding conditions. Environmental adaptation of hydraulic systems includes the introduction of synthetic esters. These new environmentally adapted lubricants (EALs) have shown very good boundary lubrication performance but also condition sensitivity. This study examines an oil lubricated bronze pin on hardened steel configuration in a reciprocating friction and wear test machine. Three synthetic esters were tested with a 1 mm stroke length. Results were compared with those for a mineral oil. The tribological performance with synthetic ester lubricant can, under certain conditions, be very good. SEM-EDS and XRD surface sensitive studies indicate the formation of a soft, copper enriched outer contact layer. The layer's nature and contact mechanisms clearly affect the performance of the different lubricants.