This case study explores the qualitative digital methods used within a collaborative self-study of teacher education practice (S-STEP). It brings together two experienced qualitative researchers working in different institutions but with an already established rapport as critical friends gained from a long-standing relationship as colleagues that began as elementary school teachers. S-STEP provided a space to be vulnerable and ask questions while examining pedagogical practices in relation to one another and a contemporary, changing field of literacy education. We look closely at our use of a virtual space for critical friend conversations that included Zoom recordings, annotations of artifacts through the Zoom interface, and the use of both automated transcripts and live note taking. These methods supported our examination of our pedagogies and identities as literacy educators in response to current sociopolitical, pedagogical, and theoretical contexts. [This content is provided in the format of an e-book.]