The Challenge
- Windows Servers were patched inconsistently across the estate
- No visibility into which servers were behind on cumulative or security updates
- Reboots were happening ad-hoc, sometimes during business hours
- Cyber-insurance renewal was asking specific patching questions leadership could not answer
Environment
- Multiple Windows Servers running production workloads
- Datto RMM available for policy-based management
- Off-hours reboot windows available with prior notice
Assessment
- Audited current patch levels across every server and role
- Reviewed which workloads tolerated reboots and which needed maintenance coordination
- Reviewed existing RMM configuration and patch policies
- Defined a staged rollout: pilot group, general population, and delayed critical systems
The Solution
- Deployed standardized Datto RMM patch policies aligned to the environment
- Configured staged rollout with pilot, general, and critical-system rings
- Scheduled monthly maintenance windows with client-communicated reboot slots
- Enabled monthly patch-compliance reporting for leadership
- Documented exception handling for servers requiring vendor-coordinated maintenance
Results
Standardized
Consistent monthly patch cadence across every Windows Server.
Improved visibility
Monthly compliance reporting available to leadership and for insurance discussions.
Reduced operational risk
Reboots moved into scheduled maintenance windows with change control.
Enhanced security posture
Time-to-patch shortened and tracked, replacing ad-hoc updates.
Technologies Used
- Windows Server
- Datto RMM
- PowerShell