Being hailed as possessing the ability to “drive effective business reengineering and management of core and support processes”, it is not surprising that Enterprise Resource Planning (ERP) systems have been adopted by more than 60% of Fortune 500 companies as at the turn of the century. In contrast, negative connotations have been commonly known to be attached to legacy systems and inhouse developed systems. But yet, some of these legacy systems are not replaced when companies adopt ERP solutions while in-house systems still continue to be developed. This research employs symbolic interactionism as the informing theoretical perspective in an ethnography study of a large government authority in Singapore. Our findings surprisingly indicate that the IS professionals supporting the systems tend to attach rather negative symbols to their SAP system, while viewing their legacy system and in-house software development work in a more favorable light. In this paper, we first describe the different symbolism that has been attached over the years to the ERP vis-à-vis legacy system. We then highlight how certain of the early symbols gradually got sedimented over time, while others did not exhibit similar permanence and presence. As a result of such symbolic realities, we demonstrate the consequent differences in attitudes of the staff involved in ERP support vis-à-vis legacy and in-house system support.