Techniques disclosed herein relate to managing transitions into fluid delivery device operating modes. In some embodiments, the techniques involve obtaining status information pertaining to operation of a fluid delivery device, the status information including fluid delivery data, exiting a closed-loop operating mode of the fluid delivery device based on the status information, and, after exiting the closed-loop operating mode, causing generation of a user notification recommending a remedial action to improve viability of a subsequent instance of the closed-loop operating mode. The closed-loop operating mode is an operating mode in which dosage commands are automatically generated based on sensor measurement data.