Modern threats like Kerberoasting, Pass-the-Hash, and credential dumping all had easier targets on 2008 R2, which lacked advanced mitigations like Defender ATP (Advanced Threat Protection) or modern just-in-time (JIT) administration found in Server 2019 and 2022.
Windows Server 2008 R2 introduced several features that improved manageability, performance, and remote connectivity: window server 2008 r2
For companies not ready to purchase new hardware, Microsoft offers Extended Security Updates (ESU) for a limited time if you migrate the server image to . This allows you to run the legacy server in the cloud with security updates while you plan your long-term migration. Modern threats like Kerberoasting
Organizations still running R2 face significant liabilities: window server 2008 r2