Bitdefender's 45-day Internal Attack Surface Assessment frames living-off-the-land binaries as an over-entitlement problem rather than a malware issue, correctly noting that 84% of high-severity incidents involve trusted utilities like PowerShell and WMIC. Yet the coverage underplays a deeper pattern: the very telemetry and hardening platforms deployed to map these binaries frequently introduce new attack surfaces through their own privileged agents, update mechanisms, and behavioral baselines that adversaries can profile and abuse. Real-world observations from environments running multiple EDR stacks show that agents like GravityZone PHASR, while reducing LOLBin exposure by 30-70%, create shadow telemetry flows that leak process metadata to cloud consoles, turning the assessment tool into a reconnaissance asset for sophisticated actors already inside the perimeter. MITRE ATT&CK's ongoing documentation of T1218 and T1059 techniques reveals that attackers increasingly target the configuration stores of security agents themselves, a blind spot the original Bitdefender analysis does not address. Synthesizing this with Gartner's 2025 forecast on dynamic attack surface reduction, where adoption is projected to surge, exposes the mechanical risk that preemptive tooling often inherits the same entitlement sprawl it aims to fix. One overlooked failure mode appears in hybrid environments where PHASR's Autopilot workflow collides with legacy admin scripts, inadvertently re-enabling remote tools under the guise of approved exceptions. The pattern is consistent across vendors: security platforms designed to observe trusted activity become high-value targets precisely because they must maintain deep visibility and rapid response privileges. Organizations must therefore treat their assessment tooling as an additional attack surface requiring the same reduction discipline applied to the endpoints under study.