A technical walkthrough of chaining Windows Server misconfigurations into full administrative compromise.
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Table of Contents
Overview
Windows Server 2016 is a Microsoft server operating system built on the Windows NT 10.0 kernel, commonly deployed to provide directory services, file sharing, web hosting, and application backends in enterprise environments.
Despite being several years old, it is still widely encountered in labs and real infrastructures, often running legacy configurations that expand its attack surface.
Microsoft IIS 10.0 is the web server role bundled with Windows Server 2016. IIS 10.0 supports modern HTTP features, integrates tightly with Windows authentication, and frequently exposes additional management or application endpoints when misconfigured.
In practice, IIS often becomes the first externally reachable service and a useful pivot point for deeper…