A system management tool, with a risk assessment mode enabled, is executed within an execution infrastructure on a management computer system, to manage a target computer system in a production situation. When the execution of the tool reaches a risk segment which raises risk for the target system, a user is informed of at least one action to be executed in the risk segment. If the user agrees, the tool is allowed to execute in an automatic mode until an end of the risk segment is reached. Feedback is obtained from the user regarding safety of the risk segment; and the steps are repeated for a plurality of additional risk segments until the tool is deemed safe for all of the risk segments, after which the tool is transitioned from the risk assessment mode to an automatic mode of operation.
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