The provided examples of systems, devices and techniques improve systems and methods for keeping users of automatic drug delivery systems engaged and assisting with the optimal use of the drug delivery system. The automatic drug delivery system may include a drug delivery device and a controller. Through the use of an attrition prevention engine in a cloud-based services system that cooperates with an attrition prevention application executing on the controller of the drug delivery device, notifications that include instructions for adjusting operation of the drug delivery device as well as offer assistance to the patient to optimize performance of the drug delivery system for the patient may be provided. Optimizing the performance of the drug delivery system has been shown to prevent attrition of patients from using the drug delivery system.