This paper compares and contrasts two projects in order to better understand the complex issues surrounding the use of technology to support parental involvement with schools and their children's learning. The Becta-funded ICT Test Bed evaluation (2002-2006) had the intention of saturating schools (in three areas of social deprivation) with a range of technologies, including 23 elementary schools. The ESRC/EPSRC/DTI-funded Homework project (2003-2006) used participatory design methods to develop and evaluate technology to link home and school in a elementary school in the South East. Both projects shared a common theoretical foundation, that of socio-cultural theory. The theory influenced the evaluation methodology employed in both projects and in the Homework project it additionally influenced the design of the technology intervention. Findings suggest that technologies with readily accessible and interactive resources that are flexible can help develop parental engagement. However, simpler and less resource hungry solutions such as the use of websites and email can provide opportunities for quick wins. In relation to transporting technology between home and school, there are issues for both staff and parents. Without purposeful use, these challenges act as a barrier once they outweigh the novelty effect. We conclude that parental needs are complex and that engagement needs to be sensitively scaffolded rather than focusing on the technology. Participatory design offers an effective means of addressing this and should be the starting point. The technology should facilitate independence and mediate access to a shared space for collaborative activity. The content and guidance needs to be purposeful and relevant, offering a means to integrate learning across the learner's broader context, including school and home seamlessly.