A computer-implemented method for gamifying the success or failure of an attempted exploitation of an endpoint connected to a network environment, the method comprising: providing agent software at an endpoint, the agent software initially configured for executing a limited set of instructions, the set comprising instructions for: selecting environment attributes; decrypting loader instructions based on the selected environment attributes decrypting a communications instruction according to the loader instructions, wherein the communications instruction is an instruction for the endpoint that specifies communications parameters according to which it will attempt to communicate with a management server over the network environment; defining an offensive team comprising of a set of one or more players, and defining a defensive team comprising of a set of one or more players, wherein the players are selected from automated processes or individuals; at the management server, on behalf of the offensive team, generating an instruction message for the agent software executing at the endpoint, wherein the instruction message comprises instructions for at least: loading a modular package of instructions for collecting specified endpoint parameters; collecting the specified endpoint parameters according to the instructions; transmitting the collected endpoint parameters to the management server; determining if the exploit is successful in execution at the endpoint; transmitting the success determination to the management server over the communications network; at the management server: receiving an indication of an exploit for execution at the endpoint from the offensive team; providing the determined exploit to the endpoint through the network environment; receiving the success determination from the endpoint; based on the success determination, updating a leaderboard configured to track statistics of the offensive team and the defensive team. providing agent software at an endpoint, the agent software initially configured for executing a limited set of instructions, the set comprising instructions for: selecting environment attributes; decrypting loader instructions based on the selected environment attributes decrypting a communications instruction according to the loader instructions, wherein the communications instruction is an instruction for the endpoint that specifies communications parameters according to which it will attempt to communicate with a management server over the network environment; selecting environment attributes; decrypting loader instructions based on the selected environment attributes decrypting a communications instruction according to the loader instructions, wherein the communications instruction is an instruction for the endpoint that specifies communications parameters according to which it will attempt to communicate with a management server over the network environment; defining an offensive team comprising of a set of one or more players, and defining a defensive team comprising of a set of one or more players, wherein the players are selected from automated processes or individuals; at the management server, on behalf of the offensive team, generating an instruction message for the agent software executing at the endpoint, wherein the instruction message comprises instructions for at least: loading a modular package of instructions for collecting specified endpoint parameters; collecting the specified endpoint parameters according to the instructions; transmitting the collected endpoint parameters to the management server; determining if the exploit is successful in execution at the endpoint; transmitting the success determination to the management server over the communications network; loading a modular package of instructions for collecting specified endpoint parameters; collecting the specified endpoint parameters according to the instructions; transmitting the collected endpoint parameters to the management server; determining if the exploit is successful in execution at the endpoint; transmitting the success determination to the management server over the communications network; at the management server: receiving an indication of an exploit for execution at the endpoint from the offensive team; providing the determined exploit to the endpoint through the network environment; receiving the success determination from the endpoint; based on the success determination, updating a leaderboard configured to track statistics of the offensive team and the defensive team. receiving an indication of an exploit for execution at the endpoint from the offensive team; providing the determined exploit to the endpoint through the network environment; receiving the success determination from the endpoint; based on the success determination, updating a leaderboard configured to track statistics of the offensive team and the defensive team.