The performance monitoring system allocates virtual machines to users or user sessions according to a user categorization that is determine using user session information and virtual machine metrics. A session monitor of the performance monitoring system is notified that a user session terminated, where the user session accessed a virtual machine. The session monitor responsively records the user session information and obtains virtual machine metrics for the virtual machine from a virtual machine performance monitor. The performance monitoring system updates a user workload profile using the user session information and the virtual machine metrics, and categorizes the user of the user session according to the user workload profile. Upon receiving a request from a user for a virtual machine, a virtual desktop infrastructure requests a virtual machine from a virtual machine manager. The virtual machine manager responsively allocates a virtual machine to the user according to the user's categorization.