This paper is based on the premise that universities have an obligation to provide adequate student support services, such as learning assistance (that is, assistance with academic writing and other study skills) and that in order to be effective such services must be responsive to the wider policy and social implications of student attrition and retention. The paper outlines briefly some of the factors that have influenced the development of learning assistance practices in Australia and America. This is followed by an account of experiences at one Australian metropolitan university where learning assistance service provision shifted from a decentralised, faculty-based model to a centralised model of service delivery. This shift was in response to concerns about lack of quality and consistency in a support model dependent upon faculty resources yet a follow up study identified other problems in the centralised delivery of learning assistance services. These problems, clustered under the heading contextualised versus decontextualised learning assistance, include the relevance of generic learning assistance services to students struggling with specific course related demands; the apparent tensions between challenging students and assisting students at risk of failure; and variations in the level of collaboration between learning advisers and academic staff in supporting students in the learning environment. These problems are analysed using the theoretical modelling derived from the tools made available through cultural historical activity theory and expansive visibilisation (Engeström & Miettinen, 1999).