Examples of the presently disclosed technology provide automated firmware recommendation systems that inject the intelligence of machine learning into the firmware recommendation process. To accomplish this, examples train a machine learning model on troves of historical customer firmware update data on a dynamic basis (e.g., examples may train the machine learning model on weekly basis to predict accepted firmware updates made by a vendor's customers across the most recent 6 months). From this dynamic training, the machine learning model can learn to predict/recommend an optimal firmware version for a customer/network device cluster based on firmware-related features, recent customer preferences, and other customer-specific factors. Once trained, examples can deploy the machine learning model to make highly tailored firmware recommendations for individual network device clusters of individual customers taking the above described factors into account.