Methods and apparatus to automatically configure monitoring of a virtual machine are disclosed. An example apparatus includes a service analyzer to: identify a first virtual machine in a first application definition, the first application definition identifying virtual machines included in a first application, the first virtual machine currently running in the first application; and detect a second virtual machine currently running in the first application, the second virtual machine not included in the first application definition; and a virtual machine analyzer to: generate a second application definition, the second application definition created by adding the second virtual machine to the first application definition; and store the second application definition in an application configuration database.