Issue during SQL Server 2008 R2 installation on Windows Server 2019 in Azure

[Luca_A215]

Hello everyone,

We are currently facing an issue while attempting to install SQL Server 2008 R2 on an Azure virtual server running Windows Server 2019. During the installation, we encounter an error with the message "Could not find the database engine startup handle." Additionally, in the system's event viewer, we encounter this error message"A fatal error occurred while creating a TLS client credential. The internal error state is 10013"

We have verified system prerequisites and executed the installation with elevated privileges, but the issue persists.

We are aware that SQL Server 2008 R2 is no longer supported, but we need to maintain and support these legacy applications until they are redesigned. Therefore, we would like to find a solution to successfully install SQL Server 2008 R2 on Windows Server 2019 in Azure, as well as in our on-premise datacenter.

If anyone has encountered a similar issue or has specific knowledge that could help us resolve this problem, we would be extremely grateful for any advice or assistance.

[#2]

@Luca_A215 

Seems not Azure but also not supported by Windows 2019:

https://bornsql.ca/blog/unsupported-but-working-versions-of-sql-server-on-windows-server-2019/

[#3]

Challenge and Limitations:

SQL Server 2008 R2 End of Support: Microsoft officially ended support for SQL Server 2008 R2 on July 9, 2013. This means security updates, non-security fixes, and free technical support are no longer available. Running unsupported software exposes your environment to potential security vulnerabilities and risks.
Recommendations:

Upgrade SQL Server: The most secure and recommended approach is to upgrade your legacy applications to be compatible with a supported version of SQL Server. This will ensure access to security updates, bug fixes, and best practices in database functionality. Consider migrating to SQL Server 2019 (the same version as your Azure virtual server) or a later supported version.

[#4 · Accepted solution]

@Emily345 

@Luca_A215 

Those dates are entirely incorrect, and with respect to the earlier statement that SQL Server 2008 R2 is unsupported on Windows Server 2019, while true, it goes one step further than that: it's unsupported on Windows Server 2016.

There were some paid-for extensions for running SQL Server 2008 R2 in Azure, but the last of those finished in July 2022.

In short, trying to run SQL Server 2008 R2 in a supported capacity in Azure is no longer possible.

From an unsupported perspective, you can give it a go - as you have done, however, if you obtained a Windows Server image from the Marketplace (as is frequently the case for IaaS solutions), you have to be aware that these are not the same as your old-school ISO-based images.

You can use ISO-based images in Azure but it is not something the faint-of-heart should try, and given SQL Server 2008 R2 is entirely unsupported, you'd be throwing cash at something (monthly) that could be a dead-end.

I'd recommend you forget all about Azure until you're ready to migrate the SQL workloads off SQL Server 2008 R2 and onto something that is supported, whether that's IaaS (i.e. SQL Server on an Azure VM) or PaaS (Azure Database or SQL MI).

But, it's your call - you just can't get any formal help with it all.

With respect to the TLS issue, you may well have to consider re-enabling TLS 1.0 - if that's even possible on an Azure IaaS machine (not something I've got the capacity to look into, but conceptually, you can edit the registry, so I'd assume it's possible).

Certainly, if you continue to run "normal" Windows Server, (even on Azure, as per the Prepare a Windows VHD article) it is possible. But you're entirely on your own in this endeavour.

References

(Some of which is quite dated now, given extended maintenance has finished.)

• Microsoft SQL Server 2008 R2 - Microsoft Lifecycle | Microsoft Learn
• SQL Server in Windows operating system - SQL Server | Microsoft Learn
• Cloud-Migration-Reference-Guide-for-the-end-of-support-for-SQL-Server-2008-and-2008-R2.pdf (microsof...
• Extend support for SQL Server - SQL Server on Azure VMs | Microsoft Learn
• Support policy for hardware virtualization product - SQL Server | Microsoft Learn
• Prepare a Windows VHD to upload to Azure - Azure Virtual Machines | Microsoft Learn

Cheers,

Lain

[#5]

@LainRobertson, thank you very much for the documentation you provided and for the insights you shared - I agree with them. However, as I mentioned previously, our objective is to maintain business continuity and ensure the functionality of the legacy application while it's being re-engineered to operate in a more modern architecture (such as SQL Azure). We're all aware of how challenging and sometimes complex it can be to modernize an application, and my role involves tackling the challenges of finding solutions that don't always align perfectly with ideal architectural standards and updates.

After a series of laboratory tests, our engineers seem to have overcome the issue: they used an image of Windows Server 2019 Datacenter Edition instead of an image of a Windows Server Azure Edition with Hotpatch. With this configuration, SQL Server 2008 works, the application functions as well, and we have control over updates.

[#6]

@Luca_A215 

Yeah, that's what the final article in the list above outlines.

Glad it's sorted.

Cheers,

Lain

[#7]

Installing SQL Server 2008 R2 on Windows Server 2019 in Azure can be problematic due to compatibility issues. SQL Server 2008 R2 is quite outdated, and Windows Server 2019 is much newer.

[#8]

I completely agree with you. However, the scenario I originally described presents me with a challenge that cannot be resolved simply by upgrading to a newer version. Our objective is to maintain business continuity and ensure the functionality of the legacy application while it's being re-engineered to operate in a more modern architecture (such as SQL Azure). We're all aware of how challenging and sometimes complex it can be to modernize an application, and my role involves tackling the challenges of finding solutions that don't always align perfectly with ideal architectural standards and updates.
After a series of laboratory tests, our engineers seem to have overcome the issue: they used an image of Windows Server 2019 Datacenter Edition instead of an image of a Windows Server Azure Edition with Hotpatch. With this configuration, SQL Server 2008 works, the application functions as well, and we have control over updates.