The engagement of parents with the education and learning of their children is known to have beneficial effects (Harris & Goodall (2007), Ofsted (2007) and DfES (2007a)). Following on from the article by Strickley (2009) which looked at the holistic view of a parental Gateway to Educational Services (GES) this paper focuses on the work, during 2009, towards the GES Connect Digitally vision (GES, 2009a). It looks, specifically from a technological standpoint, at the programme’s core services namely Online School Admissions (OSA), Online Free School Meals (OFSM), Cashless Schools and Online Payments. It then sets out the approach used by the technology workstream and examines the work done so far in establishing best practice, developing and enhancing existing technology standards and looking at new and innovative initiatives. Utilising the above framework the paper attempts to resolve the question of what the minimum features and relationships are for establishing a portal that enables the vision of multi-channel access to a core set of services for parents (GES, 2009a). It concludes that, whilst there is still a year to go for the programme, increased take-up for OSA and use of the OFSM Eligibility Checking Service (ECS) are very encouraging with signs that work on the other two areas will result in the vision stated above becoming a reality. However this needs to be tempered with the significant technological challenges of digital inclusion, identity management, open standards and interoperability.