Windows Server End-of-Service Migration Consulting

Windows Server is at the core of many PKI deployments—hosting Certification Authorities (CAs), OCSP responders, enrollment services, and other mission-critical components. As Microsoft ends support for older versions, organizations face increased security, compliance, and operational risks if migrations are not carefully planned and executed.

Choosing to postpone a migration means accepting one of two costly paths: paying for Extended Security Updates (ESUs)—an expensive, temporary measure that does not address the need to modernize—or running infrastructure with known vulnerabilities due to a lack of patching. In either case, the cost is high. ESUs carry a direct, ongoing expense, while unpatched systems carry the potentially catastrophic financial and reputational cost of a breach.

Windows Server End of Support Deadlines

Unsupported operating systems quickly become targets for exploits, and PKI-dependent services will run without vendor-supported security protections.

Why PKI Migrations Require Specialized Expertise

Migrating PKI components is not the same as moving a file server or a web server. Every element—from CA configuration to certificate templates, CRL distribution, AIA paths, and HSM integrations—must be preserved and validated. Common risks include:

• Service outages that impact authentication, encryption, or application availability
• Loss of critical CA configuration or keys
• Broken certificate chains, leading to trust failures across systems
• Compliance violations for regulated industries (healthcare, financial services, government)

Why Choose PKI Solutions

We’ve spent over a decade designing, deploying, and maintaining PKI environments for some of the world’s most security-conscious organizations. Our consulting team has extensive experience with Windows Server PKI migrations in complex, high-availability, and regulated environments.

When you choose PKI Solutions:

• Low to No Business Impact – We plan and execute migrations with an emphasis on continuity, ensuring authentication, encryption, and signing services remain online throughout the process.
• Proven Methodology – Every step follows a documented, repeatable process refined over hundreds of PKI engagements.
• Security and Compliance Focus – Migrations are performed with strict adherence to security best practices, ensuring you maintain or improve your security posture.
• Complex Environment Expertise – We handle scenarios involving Hardware Security Modules (HSMs), multi-forest AD environments, and hybrid or cloud integrations.
• Vendor-Neutral Guidance – Our recommendations are based solely on your operational needs and security requirements, not product sales.

Act Before End-of-Support Deadlines

For Windows Server 2016, the extended support deadline of 2027 is approaching quickly. Starting migration planning early ensures you can execute on your timeline, not in a crisis. For 2012 R2, the urgency is immediate every day, on an unsupported OS, as it increases your exposure.

Appendix

1. Mainstream Support

The first phase of Microsoft’s support lifecycle typically lasts 5 years after a product’s initial release.
Includes:

• Feature updates and enhancements
• Security updates
• Non-security updates (bug fixes, performance improvements)
• Design changes and new functionality
• Complimentary incident support (depending on your license)
• Ability to request product changes or new features

2. Extended Support

The second phase usually lasts another 5 years after Mainstream Support ends. Focus shifts to security over new features.
Includes:

• Security updates at no extra cost
• Paid non-security hotfixes (only if purchased separately)
• No new features or design changes
• No warranty claims

3. Extended Security Updates (ESUs)

A paid program that provides critical and important security updates after Extended Support ends. Typically offered for up to 3 years, sold year by year.
Includes:

• Critical & Important security patches only (no new features, no non-security fixes)
• Requires separate purchase (unless running in Azure, where it’s often included)
• Costs increase each year (often 75% → 100% → 125% of the original license cost per year)

4. End of Service (EOS)

The point is that when Microsoft provides no support or updates of any kind, whether security-related or otherwise.
At EOS, running the product means:

• No patches for new vulnerabilities
• Compliance risks for regulated industries
• Potential software incompatibility with newer apps/hardware