A significant area of learning design research has been the development of software applications that guide teachers' thinking as they plan, construct and revise learning events for their students. In this paper, we review conceptualisations of, and approaches to, the activity of pedagogic design and highlight the implications for the provision of computational support for this activity. We then outline different ways in which that support has been implemented in three digital tools: Phoebe, the LAMS Activity Planner and the Learning Designer. We consider the challenges to, and implications of, deploying these tools from the perspectives of three groups of stakeholders: developers, teachers and institutions. Our findings suggest that, while such tools are acceptable in principle, they face a number of technological and socio-cultural challenges to their acceptability from teachers' perspectives and to their deployment within institutional strategies for teaching and learning in a digital age.