The disclosed embodiments include a computer-implemented method for improving efficacy of diabetes self-management with automated personalized computer engagement that reliably obtains a measurement message and/or contextual information used to determine a suitable insulin dosage of an insulin titration process to treat the diabetic patient. The method includes causing display of a messaging interface that couples the user of the computing device to a chat bot simulating a health coach in a natural conversation to obtain a measurement of the diabetic patient's blood-glucose level. The method includes determining an insulin dosage recommendation to treat the diabetic patient by processing the measured blood-glucose level with an insulin titration algorithm that is personalized for the diabetic patient, and generating an electronic signal configured to cause a corresponding action to be performed by a computing device (e.g., display message of recommended insulin dosage).