It’s High Time for SQL Server Migration to Cloud: Here’s Why

Eugene Khazin

Principal and Co-Founder, Prime TSR

Extended Support for SQL Server 2008 and SQL Server 2008 R2 will end on July 9, 2019. End of support means the end of security patches. The result for organizations required to comply with HIPAA, or tasked with protecting Protected Health Information(PHI) may no longer be met, which could result in fines or penalties. Additionally, because of GDPR, being out of compliance will impact your ability to do business in Europe or retain data of EU citizens.

Migrating your applications and databases to the cloud might be the answer you’re looking for, but it’s also not your only option.

Here’s the skinny:

With limited time left to run an upgrade, you have several possibilities to explore. We filtered it down to 6 options and laid out their pros and cons.


Upgrade to a supported version of SQL Server.


Migrate to Azure SQL or Azure SQL Managed Instance.


Migrate to a Supported SQL Version with Compatibility Mode Enabled. (Stop-gap).


Commit to upgrade to Azure SQL or Azure SQL Managed Instance and receive free Extended Security Updates for up to 3 years.


Purchase Extended Security Updates for SQL 2008 R2.


Do nothing.

General considerations when migrating from SQL Server 2008 to 2017 (Azure or On-premise)

Functional compatibility testing and remediation is required

  •      Regardless of the upgrade path you take, you will still need to test all of the applications.
  •      Application testing and new environments need to be set up (up to 7 needed for each SQL Server 2008 instance).
  •      If you have 150 servers running SQL Server 2008, you will have to set up 1,050 (150 x 7) environments.

Hardware/cloud costs to support testing

  •      Considering the number of environments, the cost to acquire hardware/spin up environments is a consideration. (Faster in Azure, run when you need it in Azure) – Perfect entry point into the cloud.

Limited timeframe before support expiration

  •      You must be compliant by June 2019.
  •      If not compliant, you risk fines, especially if regulated.

The path to future upgrades: Cost, timeframe, complexity

  •      Consider the costs and timeline to upgrade servers.

Consider the cost to fix SQL Queries performance degradation issues

  •      You shouldn’t expect that upgrading to a newer software version would negatively affect performance, but because the change to SQL Server’s Cardinality Estimator is significant, you should test performance.

Compliance Considerations

Regulated companies have the most at stake during an end-of-support situation like this, since they are bound to being compliant because of HIPAA or GDPR policies.

Determining if you’re compliant is fairly cut and dry:

If you’re on an unsupported version of SQL Server, then you are not compliant. If you decide to stay on SQL SERVER 2008 or SQL SERVER 2008 R2, you either have to pay for the extended support through Microsoft or upgrade to a supported version.

Option #1 – Upgrade to Supported SQL Server (On-premise)

If going to the cloud is not in the cards for your situation, upgrading on-premise is still a great option.

Considerations and recommendations:

2017 SQL Server is the latest software version released, however, some clients may choose to upgrade to 2012. Regardless of the software version, there are a few implementation considerations to make when upgrading on-premise. You can upgrade “In-place” or “Side-by-side.” In-place means you can upgrade the data and settings without the need for a manual transfer of data or settings. This is the easiest and least time involved, however, it is the riskiest to execute. If performance or data issues arise in production, you can run into a serious problem. Side-by-side means you copy the database to another infrastructure. This gives you the flexibility to perform test migrations as well as research and resolve compatibility issues without disturbing the production system. In-place requires significantly less hardware than doing a side-by-side migration, however, our recommendation is to always replicate the environment and test it in a separate database infrastructure.

Option #2 – Migrate to Supported Azure SQL (or Managed Instance)

As you can imagine, there are plenty of white papers on the benefits of moving to the cloud. As an IT Director or CIO, the announcement to end support for SQL Server 2008 helps you present the business case as to why now is the time to go to the cloud.

Considerations and recommendations:

Option #3 – Stop-Gap Solution – Migrate to a Supported SQL Version With Compatibility Mode Enabled

For many companies, migrating to a supported version of SQL Server or Azure SQL with full testing enabled is a time and resource-intensive activity. Migrating the databases and testing the applications properly will put them well beyond the July 2019 support deadline for SQL 2008 R2.

The good news is that there is a stop-gap solution if you find yourself in this situation.

Microsoft offers a trace flag that allows you to “run as 2008” that comes standard in SQL 2017 Azure, Managed Instance, and On-premise. This allows you to run SQL 2017 with backward compatibility to 2008. You won’t get all the bells and whistles that 2017 offers, but you can be comfortable knowing you’re in full compliance.

Functional compatibility testing and remediation is required

  1. Some applications/functionality will not run on compatibility mode. This means you will have to do a full upgrade and perform full testing with 2017 functionality. Anecdotal: For a current large client of ours who has over 1,300 servers running SQL 2008, this is the option they went with. Out of the 1,300 servers, only 9 of them were unable to run in compatibility mode. So, it’s good news for many, but this still needs to be fully assessed before relying on compatibility mode to save the day.
  1. This is a stop-gap solution. Even if all of your applications run smoothly with compatibility mode enabled, you are not taking full advantage of 2017 functionality. Additionally, when the next version of SQL Server is released, you will be even farther behind in terms of the upgrade path and testing required to do the upgrade.

Option #4 – Commit to Upgrade to Azure SQL and Receive Free Extended Security Updates for up to 3 Years

Here is an excerpt directly from Microsoft’s announcement:

End of support is an ideal time to transform your IT estate with the cloud. But we know that it can be hard to upgrade everything before the end of support timeline. To address this need, we are pleased to announce that Extended Security Updates will be available for free in Azure for 2008 and 2008 R2 versions of SQL Server and Windows Server to help secure your workloads for three more years after the end of support deadline.

Considerations and recommendations:

This option gives you the time to plan and execute the future migration over a longer timeframe.

Option #5 – Purchase Extended Security Updates for SQL Server 2008 R2

Extended Security Updates will be available for purchase as we approach the end of support timeline for SQL Server and Windows Server 2008 and 2008 R2. However, we recommend customers evaluate their options now to develop a plan to modernize before the end of support deadline.

Considerations and recommendations:

We don’t have access to pricing yet, but you can bet this option will be a costly endeavor. If you find yourself in this boat, it’s our recommendation to commit to Azure because it gives you 3 years to migrate to the cloud and you will get the extended security updates for free.

Option #6 – Do Nothing  (Out of Compliance)

Doing nothing and keeping 2008 puts you at a massive risk. You will be out of compliance if you are in a regulated industry, and you will be fined a heavy amount, in addition to any other penalties that come with being out of compliance.

Considerations and recommendations:

At a bare minimum, pay for the extended support to get the latest patches. Other than that, exposing your databases to unsupported SQL Server versions is a risky endeavor.

Is Migrating to Azure Cloud Your Best Option?

Doing nothing and keeping 2008 puts you at a massive risk.

There are plenty of benefits to moving to the Azure SQL cloud, and now might be the best time to do it. Microsoft, rightfully so, has given you plenty of great options to move forward in a way that makes sense for your organization.

If you’re looking for more guidance on your migration options and searching for an azure migration partner, please reach out to Prime TSR directly.