SQL Server to Azure SQL: the four real options.

14 Jul 2026 · Microsoft Learn — SQL Server 2016 lifecycle

Extended Security Updates are available for up to three years after that, until 17 July 2029. You will hear that migrating to Azure gets you those updates free. That is not true for SQL Server 2016 — Microsoft's own documentation is explicit that the free-ESU benefit existed for SQL Server 2014 and does not carry forward to 2016. If a vendor uses free ESUs as the reason to move your 2016 estate to Azure VMs, they are working from an old deck (seeMicrosoft Learn's ESU changes for SQL Server 2016).

The four real options

1. Upgrade in place, on-premises. Perfectly legitimate, and not something we sell — it costs a version upgrade and application testing, and starts the same clock again in a few years. This option is not us.
2. Subscribe to Extended Security Updates and buy time. Available on-premises via Azure Arc or on Azure VMs; the price escalates each year, deliberately, because it is designed as a bridge and not a destination. Connecting an instance to Azure Arc is itself free. This buys time — it is Microsoft's value, not ours, and it is largely not us either.
3. Rehost to Azure VMs. Solves the hardware and datacenter problem. Doesnot solve the version problem — you still own patching, upgrades and the ESU subscription. This is Azure migration work.
4. Re-platform to Azure SQL Managed Instance or Azure SQL Database. The option that ends the cycle: these services are version-less, so there is no end-of-support date to plan around and no upgrade project in three years. Also the option most likely to need application testing, and occasionally a code change. This is where most of our Azure migration work in this area lands.

Which one is right

It depends on your application's compatibility, your licensing position, and whether you would rather spend money once or annually. Themigration readiness assessment tells you which of the four applies per database, with the cost of each — and sometimes the honest answer for a given system is option 1, even though it is the option that involves the least work for us.

Windows Server 2016 has the same problem on a different date — see the rail note on this page. If you are running both on the same box, plan them as one project rather than two.

This is one part of Azure & Microsoft Migration.