The disclosed exemplary embodiments include computer-implemented systems, apparatuses, and processes that dynamically and securely augment participants in programmatically established chatbot sessions. For example, an apparatus may obtain messaging data generated during a first communications session involving a first device and based on the messaging data, detecting an occurrence of an event that triggers an establishment of a second communications session involving the first device and a second device. The apparatus may generate and transmit, to the second device, notification data causing the second device to validate one or more authentication credentials, and may receive confirmation data indicative of the one or more validated authentication credentials from the second device. Based on the confirmation data, the apparatus may perform operations that establish the second communications session in accordance with at least a portion of the messaging data.