Context: Developing scalable methods for conversation analytics is essential for health care communication science and quality improvement. Purpose: To assess the feasibility of automating the identification of a conversational feature, Connectional Silence, which is associated with important patient outcomes. Methods: Using audio recordings from the Palliative Care Communication Research Initiative cohort study, we develop and test an automated measurement pipeline comprising three machine-learning (ML) tools-a random forest algorithm and a custom convolutional neural network that operate in parallel on audio recordings, and subsequently a natural language processing algorithm that uses brief excerpts of automated speech-to-text transcripts. Results: Our ML pipeline identified Connectional Silence with an overall sensitivity of 84% and specificity of 92%. For Emotional and Invitational subtypes, we observed sensitivities of 68% and 67%, and specificities of 95% and 97%, respectively. Conclusion: These findings support the capacity for coordinated and complementary ML methods to fully automate the identification of Connectional Silence in natural hospital-based clinical conversations.