Windows Server - Migration Pathways — Where Should Each Workload Actually Land?

Windows Server - Migration Pathways — Where Should Each Workload Actually Land?

Windows Server - Migration Pathways — Where Should Each Workload Actually Land?Floyd James
Published on: 31/07/2026

Part 1 of this series made the case for treating the 2012 and 2016 EOL dates as a single 15-month remediation window. Now the harder question: where does each workload go?

Technology CurrencyIT Compliance
Windows Server 2016  - The Second Wave

Windows Server 2016 - The Second Wave

Windows Server 2016  - The Second WaveFloyd James
Published on: 28/07/2026

The Windows Server 2012 story has run in every board room in the sector this year. The Server 2016 story hasn't. That's the mistake. Server 2012 R2 final ESU expires October 13, 2026. . Server 2016 extended support ends January 12, 2027: 91 days.

Technology CurrencyIT ComplianceESU
ESU Is a Bridge — Not a Destination Blog Post

ESU Is a Bridge — Not a Destination Blog Post

ESU Is a Bridge — Not a Destination Blog PostFloyd James
Published on: 24/07/2026

ESU Is a Bridge — Not a Destination Why Extended Security Updates should accelerate Windows Server modernization—not postpone it The executive takeaway: ESU reduces a narrow slice of security exposure while the platform remains beyond end of support

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The Windows Server 2012 R2 ESU Cliff — 3 Months Out

The Windows Server 2012 R2 ESU Cliff — 3 Months Out

The Windows Server 2012 R2 ESU Cliff — 3 Months OutFloyd James
Published on: 22/07/2026

October 13, 2026. That's the hard stop. Final ESU expires and Windows Server 2012 / 2012 R2 stops receiving security patches at any price. If you're running IT at an Ontario credit union — here's the 5-minute self-check

IT CurrencyTechnology CurrencyIT Compliance