In online courses, much of the course communication occurs in public spaces. In synchronous courses, the video and audio channels represent a shared space, and although private chat messages are possible, they may not be substantial or frequent. In asynchronous courses, discussion boards are the allocated space for communication. In these discussion spaces, the underlying expectations are that messages are public, at least to those enrolled in the course, and focused on the learning topic. Students with personal needs must independently contact instructors via email or online office hours. Conversely, instructors may only reach out to individual students once they have concrete evidence of a problem, such as a length of time without activity or missed assignments. Instructors can leave brief messages via gradebook comments, such as, "No assignment submitted." This approach to course communication is mainly transactional. This transactional approach to teaching online is efficient and fulfills the teaching-learning contract's baseline expectations. Still, it can mean that some learners experience the class with little sense of or contact with their instructor. This essay discusses how instructors can use well-timed, personalized check-in messages to shift their relationship with students from pedagogically transactional to humanized.