A food rotation and labeling system includes an alert station operatively coupled to a label maker. The label maker prints labels each having a unique identifier linked to a digital database maintained by the alert station having a processor, a memory, and a display screen. The processor is configured to store the unique identifier and associated food data including at least a preparation date and an expiration date in the memory. The processor is also configured to generate a graphical user interface (GUI) displayed on the display screen and configured to present the food data and status of each food container. In addition, the processor is configured to display an alert on the display screen and transmit the alert to a mobile device when a food container is approaching expiration or has expired.