Windows Server 2016 End of Support: Migrate and Modernize Your Estate Before January 2027

Built for the head of infrastructure or IT Director holding Windows Server and SQL Server instances at or approaching end of support, facing extended security update invoices that back-bill to the day support ended. This engagement will eliminate extended security update spend and reduce the compliance exposure of unsupported servers.

Who this is for

Infrastructure teams carrying servers at or approaching end of support, usually because the application on top of them is old, owned by nobody, and quietly critical. The trigger is typically an audit finding, a cyber insurance question, or an extended security update renewal quote. The decision this engagement forces is per instance and unavoidable: upgrade it, move it, or accept the risk in writing.

What we deliver

• A complete inventory of Windows Server and SQL Server instances against their support end dates, including the ones missing from the CMDB, with the application and business owner identified for each.
• A per-instance disposition: in-place upgrade to a supported release, rehost to an Azure virtual machine, replatform to Azure SQL Managed Instance, replace, or retire, with the extended security update cost of each path priced rather than assumed, because the paths do not all end that cost.
• Execution of the agreed dispositions with a tested rollback per instance, application validation by the owner, and a maintenance window plan that respects your actual change calendar.
• A closing compliance report enumerating every instance and its supported status, in a form that answers an audit or a cyber insurance question directly.

Outcomes our customers see

Waiting does not avoid the bill: updates bought through Azure Arc are back-billed to the end-of-support date, so enrolling 180 days late is invoiced for those 180 days too. Moving a SQL Server instance to Azure SQL Managed Instance ends its extended security update charge rather than reducing it, removing 100 percent of that line item, because Microsoft cancels the subscription on migration. Outside Azure those updates run at 100 percent of the full license price in every year they are available, which is why each path is priced rather than assumed.

How this compares

This is deliberately narrow: an end-of-support remediation with a compliance report at the end, which is what the audit finding asked for. Our Azure Migration Delivery offer is the one for a datacenter exit run on a wave plan; this one answers a support date and stops when the estate is supported. The commercial lever is knowing which path ends the bill, and the answer differs by product. Windows Server updates are free on Azure virtual machines. SQL Server 2016 updates are a paid subscription there just as they are on-premises, so only an upgrade to a supported release or a move to Azure SQL Managed Instance retires that line item.

Architecture and Microsoft alignment

Discovery runs through Azure Migrate, Microsoft Configuration Manager or Microsoft Defender for Endpoint inventory, and Microsoft Entra ID device records to catch instances outside the known estate. Remediation paths are in-place upgrade to a current Windows Server release, rehost to Azure virtual machines where Windows Server extended security updates carry no charge, or replatform to Azure SQL Managed Instance using the Azure Database Migration Service. Instances that must stay outside Azure connect to Azure Arc, the subscription path for their updates rather than a free one. Azure Update Manager and Azure Policy enforce the supported state after remediation. Aligned to the Microsoft solution plays Migrate and Modernize Your Estate and Unify Your Data Platform.

Plans

Plans, prices, and full scope per plan are on the Plans tab of this listing.

Prerequisites

Administrative access to the source estate for discovery, an Azure subscription where the Azure remediation paths are chosen, application owner availability for validation testing, and a change window agreement. Where an application vendor does not support a current operating system version, that constraint must be surfaced during discovery rather than at cutover.

Limitations

Applications requiring code changes to run on a supported platform are identified and quoted separately. Non-Microsoft operating systems and appliances are inventoried but not remediated. Where the business accepts the risk on an instance, that acceptance is documented and the instance is excluded rather than silently omitted from the compliance report.

How to buy

Buy through the Azure portal, using Get it in Azure portal on this listing, so the purchase is billed through your existing Microsoft agreement. Private offers on request.

Next step

Get it now in the Azure portal, or request a private offer if the scope or the price needs adjusting first.