During the Spring 2020 semester, K-12 teachers throughout many parts of the world adapted from face-to-face to online teaching. To better understand these experiences, seven advanced placement (AP) Statistics high school teachers were interviewed following a semi-structured protocol. A collaborative and consensus-driven analysis of transcripts revealed 12 distinct themes. The three most extensively discussed themes appeared to be "assessment" (19.11%), "communication methods" (12.23%), and use of "online instructional approaches" (11.90%). Teachers from schools that did not provide devices to students (i.e., not "one-to-one") tended to report concerns around digital access more frequently (6.87%) and tended to express a more negative sentiment ("Sentiment Mean" = -0.09) than teachers at schools that provided devices (5.69%; Sentiment Mean = 1.35, p < 0.01). These findings highlight issues facing teachers during the transition to remote and online instruction and suggest a need for supporting teachers in developing familiarity with online and remote assessment resources and strategies.