Information retrieved from monitoring agents currently installed on instrumented entities within a system is analyzed to discover additional entities within the system that are connected to the instrumented entities. Each of these discovered entities is analyzed to determine whether a monitoring agent is able to be installed within the entity; if installation is possible, such installation is automatically performed (or a guided manual installation is implemented utilizing an interface). After a monitoring agent is installed within a discovered entity, information is retrieved from that monitoring agent and is used to discover additional entities within the system that are connected to that discovered entity. In this way, an iterative discovery of all entities within a system may be performed.