SQL Server 2016 left extended support on 14 July 2026. Eligible production workloads need ESU coverage to receive subsequent critical security updates while they remain on that version.

That leaves three choices: pay, upgrade or move. The risk is making one choice for the whole estate.

What changed

Record which production instances have ESU coverage and which remain without it. Qualifying non-production and disaster recovery benefits can differ; check their conditions. The answer matters in security reviews, insurance renewals, compliance reviews and licensing true-ups.

SQL Server 2016 ESU years end on 13 July 2027, 18 July 2028 and 17 July 2029. ESUs provide critical security updates when available. They do not restore normal product support, general bug fixes or new features; Microsoft may include non-security fixes at its discretion. They are a temporary bridge, not modernisation.

Waiting does not lower the ESU bill. For a first SQL Server 2016 ESU subscription through Azure Arc, Microsoft bills for the missed part of the current ESU year. If you first enrol in a later year, you must also buy coverage for the previous ESU years. A business that enrols in January 2027 is billed for the months it missed since July 2026. What waiting does shorten is the time left to plan before the first ESU year ends on 13 July 2027.

The three choices

Pay. Buy ESUs and keep the workload where it is while you plan. This suits a server that must stay put for now: a system mid-project, an application with a fixed retirement date, or an ERP such as Microsoft Dynamics GP with a planned replacement, where ESUs can bridge the gap instead of an upgrade.

Upgrade. Move to a supported SQL Server version where the workload already runs. This suits servers with years of life left, as long as the applications on them support the newer version.

Move. Migrate to a supported SQL Server version or supported Azure service where application compatibility and the business case fit. Moving SQL Server 2016 unchanged to an Azure VM still requires separately paid ESUs for eligible production coverage; the move alone does not restore its product lifecycle.

Each of these can be the right answer. Rarely for every server at once.

Licensing is a separate question

Existing rights, PAYG through Arc and SQL Server subscription licensing answer how the workload is licensed. None alone restores SQL Server 2016 security updates. Eligible ESUs, an upgrade to a supported version or migration to a supported target address that separate lifecycle question.

The licensing answer differs per workload too. Take two servers on the same version. One runs a finance system around the clock on existing licences with Software Assurance. The other is a project server that only runs for part of the year. Keeping the existing licences on the first may cost little. Paying for a full year of licensing on the second may not make sense, and PAYG billing could be worth a look. Both still need a support answer.

You cannot tell which is which from a licence list. You need the cores, the run hours, the configuration and the licences and Software Assurance you already have, server by server.

What each lead needs before deciding

The head of IT needs one inventory of every SQL Server in the business, with the risks ranked and an owner on each. Without that, an ESU quote can cover servers nobody needs and miss the ones that matter.

The financial director needs the options compared per workload in one currency, rand or dollars, never mixed. The VAT basis, any ESU back-bill and every assumption should be written down, so the numbers survive a second look.

The licensing lead needs licences, Software Assurance, subscriptions and renewal dates checked against Microsoft’s Product Terms before any order. A misread licence term can be expensive to unwind.

Three things to watch for

Assessment estimates. Arc Migration Assessment fixes its region at West US, currency at USD and uptime at 732 hours per month. Benefits and reservations can be configured. Those fixed outputs are not a customer quote. Braintree builds a separate indicative comparison using current pricing for the customer’s region, currency, run hours and rights, with assumptions, FX date and VAT basis shown.

Charges on separate lines. Log Analytics monitoring data for the Best Practices Assessment can add Azure charges, and Microsoft Defender for SQL is a separate service with its own price. Partner service time is charged separately too. Ask to see each one on its own line.

“Free” assessments. Microsoft’s Migration Assessment carries no charge on eligible Arc-connected instances. The access, setup and partner time around it are a different matter, so ask what is included.

Know before you license

That is where we start. The SQL Estate Assessment is a fixed-scope Braintree service that ends in a decision pack for each workload:

• Inventory and assessment eligibility, including any blind spots.

• Configuration and compatibility findings, each with a severity, an owner and a next action.

• Migration readiness and indicative sizing.

• Your existing licences: edition and actual licensing metric, including core-based or Server+CAL; CALs where relevant, Software Assurance or subscription, term, and high availability and disaster recovery (HA/DR) treatment.

• A cost comparison in one stated currency, with Azure usage, licensing, any ESU back-bill and our fees on separate lines.

• Two recommendations per workload: a security-update or supported-target plan, and the licensing basis. Include eligible ESUs as an ERP bridge where suitable, prerequisites and any issues to address first.

If the evidence says a workload’s licensing should stay exactly as it is, the pack says so.

What the assessment needs from you

Before discovery starts, we agree in writing which servers are in scope, the access we need, who is involved on your side (IT, your DBA and, for ERP workloads, your ERP master user), the dates, and how your data is handled. Discovery is scheduled around your month-end and year-end close.

To produce Microsoft’s assessment output, each in-scope server is connected to Azure Arc. That means:

• Installs on each server: the Azure Connected Machine agent and the SQL Server extension. The Best Practices Assessment also needs Azure Monitor Agent and a Log Analytics workspace, which can add Azure charges.

• Access: an administrator or service account for the installs, an Azure subscription to register the servers in, and outbound connectivity from the servers to Azure.

• Eligibility: Microsoft’s Migration Assessment covers Windows-based SQL Server 2014 or later on Windows Server 2016 or later and excludes failover cluster instances. Best Practices Assessment needs a qualifying licence type. Server+CAL instances must be registered as LicenseOnly even with active Software Assurance, so do not assume they qualify for that BPA output. Eligible instances can still receive Migration Assessment. Instances outside eligibility are inventoried and compared without the unavailable output.

• Afterwards: whether the agents stay connected or are removed once the decision pack is delivered is agreed in writing at the start.

Connecting to Arc for assessment does not move your databases or automatically change SQL Server licensing or activate PAYG. We record your actual current licence basis. Braintree assessment fees and additional Azure charges, including Log Analytics where used, are agreed separately.

Assessment onboarding is part of the assessment. A later licence change, ESU purchase, upgrade, migration or managed service is separately approved, scoped and quoted after the decision pack. Full SQL maintenance and backup-only support are possible service routes; responsibilities, exclusions and service levels require the approved schedule and signed terms.

Why Braintree

For 10+ years we have helped 220+ South African businesses grow, and our team includes 100+ Microsoft-certified professionals. We recommend per workload and quote Azure usage, licensing and our services separately, so you decide on evidence.

Request your SQL Estate Assessment.

Specialists in Business Applications, Modern Workplace and Azure.

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