This article is premised on research that suggests there is a gap between technology use for teaching and learning and the technology used in assessment. Digital technology such as blogs, Facebook, Twitter, podcasts, and news feeds are increasingly used in teaching and learning. On the other hand, assessment is often only in traditional essay form and frequently via pen and paper. This article examines the complex nature of multimodal design and argues for assessment that has constructive alignment, which sets out the interdependence of learning outcomes, teaching, and assessment where all three are aligned as equal partners. The aim of the research described was to investigate whether teacher-learners believed there was alignment between learning outcomes, activities, and assessment that utilized digital media technology. This article presents findings from a small-scale case study that drew on qualitative data from Student Evaluations of the Paper and from online surveys from four cohorts of participating teachers in a postgraduate adult literacy, language, and numeracy professional development program. There were three important findings from the data that indicated the importance of firstly having alignment of digital technology and course design outcomes, activities, and assessments and that this was clearly visible to the participants. The second finding indicated the content was relevant to the teacher-learners and involved them in constructing their own learning through authentic and practical activities and assessment. The third finding indicated that course outcomes, activities, and assessment tasks were aligned with multi-literacy skills. It is argued that academics design courses that are constructively aligned connecting learners with outcomes, activities, and assessment, which include an explicit focus on teaching the multi-literacy skills required in a world that is becoming increasingly digital.