Practical guide to upgrading SQL Server 2016 to newer versions
A practical decision-making guide for organizations using SQL Server 2016 and considering a transition to SQL Server 2019 or SQL Server 2022.
Extended Support for Microsoft SQL Server 2016 ended on 14 July 2026, and the key question when planning an upgrade is not which version of SQL Server is the latest, but which version we need for our applications, infrastructure, security requirements, and plans for the coming years.
In some environments, it may make sense to gain additional time through the Extended Security Updates (ESU) program. In others, moving to SQL Server 2019 may be the appropriate step, while SQL Server 2022 will often be more suitable for database platforms planned for long-term use.
Here is a guide to help you find the most suitable solution based on your company’s needs.
1. Start with the reason for the change
Before comparing the features of individual versions or licence prices, define why you are considering a change. This will have a significant impact on which target version and migration method make sense. For example, you may be dealing with one of the following situations:
End of support – SQL Server 2016 is no longer within the standard support lifecycle. If you want to continue receiving regular security updates from the vendor, you need to choose a newer supported version or temporarily use the ESU program.
Application requirements – A new version of an ERP, CRM, accounting system, or internal application requires a newer SQL Server, or its vendor no longer supports the application on the older version.
Performance and capacity – The current environment is reaching its performance limits. Moving to a newer version may provide access to newer database processing optimizations and better handling of growing data volumes.
Security and regulatory requirements (compliance) – You want more modern security features, a longer period of regular updates, or need to meet internal rules and external IT security requirements.
Infrastructure refresh – You are changing hardware, the virtualization platform, or Windows Server and want to combine this change with an upgrade of the database layer.
Costs and licensing – You are looking for a stable perpetual licensing solution and want to optimize overall costs. This is not only about the licence purchase price, but also the number of licences required, virtualization, migration costs, and future operation.
If it is not clear why the organization is considering an upgrade, it is not yet the right time to choose a specific version. First, you need to define the planned operating horizon, review application dependencies, and describe the technical limitations. Only then does it make sense to compare SQL Server 2019 and SQL Server 2022.
2. Support duration is a key difference
From a lifecycle perspective, SQL Server 2022 clearly offers a longer-term outlook. SQL Server 2019 entered Extended Support in February 2025, and Microsoft provides security updates for it until 8 January 2030. In contrast, SQL Server 2022 has Mainstream Support until 11 January 2028 and Extended Support until 11 January 2033.
Version | Mainstream Support | Extended Support | ESU / additional period |
|---|---|---|---|
SQL Server 2016 | 13 July 2021 | 14 July 2026 | ESU until 17 July 2029 |
SQL Server 2019 | 28 February 2025 | 8 January 2030 | Standard lifecycle |
SQL Server 2022 | 11 January 2028 | 11 January 2033 | Standard lifecycle |
If you are building a database environment for the long term in 2026, SQL Server 2022 offers a longer support horizon. SQL Server 2019 may still be a suitable choice, particularly when compatibility with a specific application plays a decisive role, when you need to make a smaller and more conservative change, or when you are planning another major modernization before 2030.
3. When to choose SQL Server 2019
SQL Server 2019 may be a suitable choice if the vendor of your key application certifies or recommends it as a proven platform. You should also consider it if you want to make the transition from SQL Server 2016 gradually, do not need support until 2033, and expect another significant infrastructure change within the next few years.
A specific licensing offer may also be a reason. If SQL Server 2019 is more economical in your particular scenario and support until January 2030 fits your plan, choosing the newer version is not automatically more beneficial. SQL Server 2019 may also make sense if you will not use the features that SQL Server 2022 newly introduced or significantly expanded.
However, take into account that SQL Server 2019 no longer receives Mainstream Support. You should therefore have a specific technical, operational, or economic reason for choosing it.
4. When to choose SQL Server 2022
Consider SQL Server 2022 if you want to operate the database platform for many more years and do not want to deal with another end-of-support project in the foreseeable future. This option is particularly suitable if your applications support it and if you are already planning a broader migration or infrastructure refresh.
Another argument for SQL Server 2022 may be its newer security, availability, performance, and management capabilities. The platform includes, for example, authentication through Microsoft Entra, the ledger feature for verifying data integrity, Query Store hints, contained availability groups, and expanded integration options with Azure services.
New features alone are not a reason to upgrade. If you will not use them, they should not be the main criterion in your decision. In practice, the combination of support duration, application compatibility, operational requirements, and licensing costs will usually be more important.
5. Quick comparison of versions
The following table is intended to provide quick guidance, not an automatic purchasing recommendation. The final decision must always be based on the specific combination of your applications, infrastructure, and licensing setup.
Situation | SQL Server 2019 | SQL Server 2022 |
|---|---|---|
The longest possible lifecycle is the priority | Rather not | Strong choice |
The application is validated only for 2019 | Strong choice | Verify |
I want a conservative transition and another modernization before 2030 | May make sense | Compare |
I am building a new environment for 5+ years | Weaker choice | Strong choice |
I want to keep Windows Server 2016 | Yes | Yes |
I need the latest features from the 2022 generation | No | Yes |
Purchase price is the deciding factor | Compare offers | Compare offers |
6. What about SQL Server 2025?
SQL Server 2025 is already available on the market, but this does not mean that every migration from SQL Server 2016 has to move to this version. Microsoft lists Windows Server 2019 or later as a supported server operating system for SQL Server 2025. In contrast, SQL Server 2019 and SQL Server 2022 also support Windows Server 2016.
If you therefore want to keep your existing Windows Server 2016 and modernize only the database layer, versions 2019 and 2022 may be more practical alternatives.
This is a good example of why “latest” and “most suitable” are not synonyms.
7. Upgrading SQL Server does not necessarily mean changing Windows Server
According to Microsoft documentation, both SQL Server 2019 and SQL Server 2022 can run on Windows Server 2016, 2019, 2022, and 2025. You therefore do not automatically have to change the server operating system together with the database platform.
If you are nevertheless considering modernization, you can divide it into stages. You can first move to a newer SQL Server and only later address the future of Windows Server or the hardware. This approach is particularly suitable when the current operating system still meets technical requirements, your applications depend on it, or changing the database, operating system, and hardware at the same time would increase the scope and risk of the project too much.
8. Check your applications first
The database platform does not operate in isolation. SQL Server often runs ERP and CRM systems, accounting software, reporting, manufacturing applications, and custom internal solutions. Before upgrading, it is therefore not enough to verify whether moving to a newer version is technically possible. You also need to determine whether the target version is supported by all applications and components on which your operations depend.
When preparing the migration, focus particularly on the following areas:
Support from application vendors – For each key application, confirm which SQL Server versions its vendor supports.
Drivers and integration layers – Check the drivers, middleware, and other integration layers used between the database, applications, and surrounding systems. Hidden dependencies may become apparent here during an upgrade.
Compatibility changes – Review features that the newer version changes, marks as obsolete, or no longer supports. In Microsoft documentation, you will mainly encounter the terms breaking changes, meaning changes that may disrupt existing functionality; behavior changes, meaning changes in system behaviour; and deprecated features, meaning obsolete features intended for future removal.
Server objects and related services – Include SQL Server Agent jobs, linked servers, logins, SQL Server Integration Services and SQL Server Reporting Services components (SSIS/SSRS), replication, and High Availability scenarios in your review. These elements may not be part of the database itself, but they can still be essential to application operation.
Testing outside production – First test the databases and applications in a non-production environment. Only after verifying compatibility, performance, and key operational scenarios should you plan the change in the production environment.
For an initial technical assessment, you can also use the migration component in SQL Server Management Studio. It can evaluate breaking changes, behavior changes, and deprecated features, and help with the migration of databases and logins. However, even a technically supported upgrade path does not replace your own assessment of the environment and thorough testing.
9. A direct upgrade to SQL Server 2022 is possible
If you are using SQL Server 2016 with Service Pack 3 or later, Microsoft supports a direct upgrade to SQL Server 2022. You therefore do not technically need to go through SQL Server 2019 as an intermediate step. A direct transition from SQL Server 2016 to SQL Server 2019 is also supported.
10. In-place upgrade or side-by-side migration?
The fact that a particular path is technically supported does not mean that an upgrade directly within the existing installation (in-place upgrade) is always the best option. If you operate a critical environment, consider a side-by-side migration to a new instance. This gives you more time for testing, the option to switch applications gradually, and an easier return to the original environment if complications occur.
When choosing between the two approaches, consider the criticality of the system, availability requirements, acceptable downtime, and how easily you could reverse the change if necessary.
The following table provides a quick comparison of both options:
In-place upgrade | Side-by-side migration |
|---|---|
Upgrade the same instance to a newer version | New instance alongside the original environment |
Less new infrastructure and simpler topology | Better conditions for testing and gradual switchover |
Less room for parallel testing | Easier return to the old environment if a problem occurs |
Rollback may be more complicated, so preparation and backups are essential | Databases and server objects must be transferred, and temporary parallel capacity is required |
11. Edition and licensing model can change the economics of the project
When upgrading, you do not automatically have to keep the same licensing scenario you use today. If you are changing servers, the number of cores, the virtualization architecture, or the number of users, the number of licences required and the overall cost of the project may change significantly.
Under Microsoft’s current model, SQL Server Standard can be licensed by processor cores or under the Server + CAL model. SQL Server Enterprise is licensed by cores and is intended mainly for more demanding scalability and advanced scenarios. The two editions differ not only in price, but also in functional limits and the availability of individual features.
In a virtualized environment, verify whether licences apply to specific virtual machines or to the broader physical infrastructure. Always assess the specific rules according to the licensing rights of the particular scenario. If you are purchasing secondary perpetual licences, also verify their origin, licensing model, and the completeness of the transfer documentation.
Therefore, do not start with the question of how much SQL Server 2022 costs. First determine which edition you need, the extent to which you will operate the platform, and how many licences you actually require. Otherwise, you may reduce the price of the product itself, but not the total cost of the project.
12. When you can temporarily stay on SQL Server 2016
Even after the end of Extended Support, you do not have to leave this platform immediately. The paid Extended Security Updates (ESU) program is still available and provides critical security updates until July 2029. It is not inexpensive and addresses only serious security threats.
Even so, temporarily remaining on SQL Server 2016 may be a rational decision if you have a clear reason and follow a specific plan.
Such a situation may arise, for example, when your key application does not yet support a newer SQL Server, or when the migration is part of a larger project with a predefined completion date.
In any case, assess the risk, ensure appropriate protection of the environment, and establish a clear migration schedule. Running SQL Server 2016 after the end of support is therefore not necessarily a problem in itself. The risky situation is using an unsupported version without security measures, without a modernization plan, and without a deadline for deciding on the future solution.
13. Decision map
The following set of questions can help you quickly assess which alternative to the latest Microsoft SQL Server 2025 version to choose:
Question | What it means |
|---|---|
Do you need to postpone the migration? | Consider ESU as a temporary solution and set a firm migration deadline. |
Do you need to keep Windows Server 2016? | SQL Server 2019 and 2022 support it. SQL Server 2025 does not. |
Is your application certified only for SQL Server 2019? | SQL Server 2019 may be more practical if its lifecycle until 2030 fits your plan. |
Are you building a platform for 5+ years? | SQL Server 2022 offers a significantly longer support horizon, until 2033. |
Do you need the new features of version 2022? | If they provide real benefits for you and your applications support them, this strengthens the case for SQL Server 2022. |
Is price the main deciding factor? | Compare the specific 2019 and 2022 licensing scenarios, not just the price of a single licence. |
Is the migration critical and do you need the certainty of an easy rollback? | Consider a side-by-side migration and thorough testing before switching to production. |
14. Checklist before migrating to a newer version
A successful migration to a newer version of SQL Server does not begin with installation, but with thorough preparation.
Use the following list as a basic framework for this preparation. For critical systems, expand it to include your own operational, security, and regulatory requirements.
Environment inventory
Create an inventory of all SQL Server instances, including the versions, editions, Service Packs, and cumulative updates in use.
For each database, record its owner, size, criticality, and required RTO and RPO values, meaning the target recovery time and the maximum acceptable amount of data loss.
List the applications that depend on SQL Server and confirm compatibility with the target version with their vendors.
Technical readiness
Check whether the current operating system, hardware, and other software meet the requirements of the target version.
Evaluate changes that may break compatibility, change system behaviour, or affect deprecated features.
Review logins, SQL Server Agent jobs, linked servers, credentials, and other server objects.
Check SSIS, SSRS and Analysis Services components, replication, log shipping, and High Availability configurations.
Testing and rollback
Before making the production change, create a full backup and perform a verified restore test.
Record the performance parameters of the current environment so that you can compare them with the resulting state after migration.
Test the databases, applications, and key operational scenarios in a non-production environment.
Decide whether you will upgrade the existing instance or perform a side-by-side migration to a new instance, and prepare a rollback plan in case of complications.
Licensing and project organization
Confirm the target edition, licensing metric, number of required licences, and the impact of virtualization.
Plan the maintenance window, assign responsibilities, and prepare a communication plan for users, administrators, and vendors of connected applications.
15. Do not choose a version based only on its number
SQL Server 2019 may be a reasonable choice if you operate a compatible environment and plan to use it over the medium term. SQL Server 2022 offers a significantly longer lifecycle and generally makes more sense for a platform that you want to operate for many more years.
In some cases, however, temporarily postponing the migration may be the right decision. Use the additional time to prepare a safe and feasible transition, not merely to postpone the problem.
Forscope has both SQL Server 2019 and SQL Server 2022 available and can help you compare the appropriate version, required edition, licensing scope, virtualization scenario, and options for gradual modernization. The goal is not to sell the latest product, but to design an option that matches your actual needs and budget.