As “teaching libraries,” many academic libraries are committed to teaching not only in classrooms but also at the reference desk. As reference has expanded to include digital modes of e-mail and chat, reference librarians are prompted to consider approaches to teaching in these new reference venues in ways that are meaningful to the user. A promising approach to teaching through digital reference is the application of the ACRL Information Literacy Competency Standards. This paper presents some challenges and benefits of teaching via digital reference. Practical methods for promoting self-directed learning by examining online instruction, and suggestions for effectively advancing a pedagogy based on the ACRL Information Literacy Competency Standards, are offered.