top of page

Windows Server 2012 and 2012 R2 Reaching End of Support


After October 10, 2023, these products will no longer receive security updates, non-security updates, bug fixes, technical support, or online technical content updates. Many industries enforce strict regulations regarding software usage, data protection, and cybersecurity. Using expired software versions can lead to non-compliance, resulting in legal and financial repercussions. Updating expiring software versions is not merely about staying up-to-date; it is a fundamental step in maintaining security. Cybersecurity threats are continuously evolving, with software vulnerabilities being a prime target for attackers. Software updates don't just address security, but they also bring performance enhancements and new features. By updating expiring software versions, users can experience improved performance and gain access to the latest tools and capabilities.

Remediation Options

There are three options to address the issue of expiring Windows operating system versions:

  • Migrate to cloud.

  • Upgrade Windows OS on-premises.

  • Deploy extended security updates on-premises.

Let us embark on a brief exploration of these three alternatives, with a focus on their primary characteristics.

1. Migrate to Cloud & Upgrade

It could lead to a lengthy discussion, weighing the pros and cons of migrating a server to the cloud. However, that's not the focus of this article. Upgrading the operating system could serve as a compelling reason to transition to cloud solutions, especially if it aligns with the company's strategic plans. Nevertheless, if we were to explore that direction, it could potentially prove to be a valuable long-term investment in our modernisation journey. Cloud service providers offer a range of tools to facilitate this challenging task, such as:

  • Azure Migrate

  • Virtual Machine Readiness Assessment

  • AWS Cloud Adoption Readiness Tool (CART)

  • CloudEndure

  • BMC Discovery

  • Google Cloud Migration Center

and more. While various tools are employed for migration across different cloud platforms, the migration approach remains similar.

It is essential to highlight a notable offering from Microsoft, which is 'Migrate to Azure, run securely with free Extended Security Updates.' With this option, customers have the opportunity to migrate their applications to Azure Virtual Machines and receive free Extended Security Updates for up to three years after the end of support. Furthermore, customers can leverage Azure Hybrid Benefit to achieve significant cost savings on Azure, as it allows them to use their existing Windows Server licenses on the cloud without incurring any additional expenses.

2. Upgrade On-Premises

Upgrading the operating system version on-premises is a common practice, but it can introduce potential challenges, especially regarding the uninterrupted operation of installed applications. In this context, there are primarily two options to consider:

  • an in-place OS upgrade, or

  • migrating applications to freshly installed servers.

The choice of approach should be determined through analysis of the technical feasibility of the various applications and the availability of temporary resources. In many instances, there are still compelling reasons to remain on-premises. That being said, we recognise that Windows Server supports numerous business-critical applications that may require extended time for modernisation.

3. Deploy Extended Security Updates

Customers who have Software Assurance or subscription licences under an enterprise agreement enrolment but are not able to meet the end of support deadline will have the option to buy Extended Security Updates to get three more years of security updates for Windows Server 2012 and 2012 R2. This provides some time for planning for applications modernisation. Conveniently, with Extended Security Updates, customers can continue to protect these applications while modernising.


Choosing the right approach may initially appear to be a straightforward task, but within an IT ecosystem, the operating system is just one of many interconnected elements that must follow a strict sequence. The right choice requires consideration of various factors, including environmental specifics, service dependencies, and financial considerations. It involves an in-depth analysis of current solutions and planning the future model aligned with the company's strategies.

That's why Nuwey engineers, drawing from their extensive experience in upgrading operating systems, established a concise set of criteria that is used when planning such operations. The upgrade project flow is designed in three phases:

Phase 1: Readiness
  • Understand Clients’ Business Strategy - Identified business reason to stay on-premises or move to the cloud. Sponsor’s readiness to sign-off the migration and funding.

  • Discovery & Assessment - Workload discovery and assessment using respective toolset and analysis methodology. Involve application owners to identify scope, dependencies, and migration approach.

  • Cost-Benefit Analysis - Assess the upgrade techniques and how they fit to the goals and whether it is a worthwhile investment.

  • Establish a Project Governance Crew – Strong team to drive and establish collaboration and communication between the stakeholders. Align on the project schedule.

  • Risk Assessment - Identify potential challenges and mitigate the risk and prevent negative business impact.

  • Regulatory Compliance - Guarantee that the enhanced product adheres to pertinent regulations and standards, particularly in sectors characterised by rigorous compliance mandates.

  • Resource Allocation - Determine the resources needed including skillset, software and potential equipment.

  • Training of the Technical Teams and Users if Needed - Plan how you will communicate the upgrade to users and provide any necessary training or documentation to help them adapt to the changes.

Phase 2: Initial Execution
  • Technical Considerations – Consider the technical requirements to deploy new or evaluate the compatibility of the available systems.

  • Confirm and Fine-Tune the Migration, Backup and Rollback Plans - Ensure that the migration and backup plans are in place to prevent corruption and business impact.

  • Setup Cloud Landing Zone – In case of migrations to cloud confirm the design to accept migrated workloads.

  • Define and Migrate/Upgrade a Pilot Scope – Proof of execution. Overcome the initial inconvenience with changes.

  • Quality Assurance - Comprehensive tests to assess the upgraded systems’ functionality in accordance with the quality standards.

Phase 3: Mass Migration
  • Upgrade and Migration Execution – Have a well-prepared technical team as assembled in the previous stage that is ready to execute a comprehensive big-bang scope.

  • Migration and Post-Migration Monitoring and Support – Have a plan about how to support the services during and after the project. Ensure monitoring the health and performance of the systems and applications.


By conducting a thorough analysis of the current on-premises assets, defining the scope, and carefully considering all steps and key points in an upgrade project, you can develop a robust business case supported by a secure financial rationale grounded in a cost-effective pricing proposition.

NUWEY's teams with its extensive experience in resolving these challenges within large client environments, is at your disposal to assist and guide you in successfully tackling this task and bringing it to a successful conclusion. Contact us if you are looking to upgrade your Windows Server 2012 and 2012 R2 workloads or migrate them to Azure, AWS or GCP.

51 views0 comments

Recent Posts

See All


bottom of page