Systems, devices, methods, and computer readable media for determining potential issues with a software upgrade are disclosed. In one implementation, the disclosed system includes at least one processor and at least one non-transitory memory storing instructions to perform operations when executed by the at least one processor. The operations include training a machine learning model on historic trouble ticket data; receiving data relating to a planned software upgrade; providing the received data to the trained machine learning model, wherein the trained machine learning model generates a tag value; calculating a risk score based on the tag value; and determining a client-specific action to be performed relating to the planned software upgrade and based on the risk score.