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Summary
Milton Webster's team was losing the catch-up game on patching: annual reviews kept showing machines behind schedule and risk scores high, with nothing keeping pace in between. After an affiliate's recommendation, they paired Rapid7 endpoint risk scoring with Automox remediation. A new laptop now joins the network near a million in risk and normalizes to under 1,000 by the next morning, and the site-wide average per machine fell from the millions to under 50,000. Milton also covers a Windows 11 upgrade worklet that ran off the team's own ISO and surprised them by working. He plans to consolidate onto Automox remote control. He also describes an internal reboot campaign called Wednesday's WeBoot that turned patch reboots into accepted routine.
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