How to Upgrade SQL Server 2008 to 2016

Since July 9th, 2019, Microsoft has discontinued complete support for both the SQL Server 2008 and SQL Server 2008 R2. 

Hence for most of us who continue to remain on the SQL 2008 versions, this does mean that we will need to force an upgrade for the software to ensure the system continues to work securely because getting a security breach is the last thing we need. /s

Now there are tons of great options to choose from if you’re deciding on which SQL Server version to upgrade to. This includes Postgres, Azure SQL, SQL Server 2016, SQL Server 2017, SQL Server 2019. We will be writing a complete comparison guide on this, so if you’re interested, subscribe to stay notified of when the content is published. 🙂

For the purposes of this guide, we will guide you step-by-step on how to upgrade SQL Server 2008 to 2016, although the steps still apply if you’re considering the other SQL Server versions. Do take note that you cannot upgrade to either SQL Server Express or SQL Server Developer versions as they are no longer supported.

Before you jump in and start getting your hands dirty, do take note that of the following notes to understand more about the upgrade process beforehand:


What you will need to know

  • If you’re upgrading from SQL Server 2008 to a newer SQL Server version such as 2016, 2017, or 2019, then the upgrade process will overwrite the SQL Server 2008 version. 
  • This is why it is crucial to backup your SQL Server data before you proceed with the steps below on this page. Microsoft has provided excellent documentation on how to backup SQL Server 2008 should you require a reference.

Once you’ve made sure of the above requirements, we can begin. 



How to Upgrade SQL Server 2008 to 2016: 10 Steps


  1. Firstly, you will want to get a hold of your new SQL Server installation media and insert it. 

Help! How do you locate the SQL Server installation media? 

It can be tricky to locate the installation media especially if you’re new to all this. What you can do, as suggested by user Watki02 over on a similar Stack Overflow thread is to use the SQL Server 2016 executable and run it. Next, from the SQL Server Installation Center, navigate to the Options tab from the sidebar and then copy the Installation Media Root Directory (as shown below). 

Lastly, paste this path into the open “Browse for SQL Server Installation media” window and you’re ready to proceed to Step 2.

Help! Where do I get to a SQL Server 2016 executable file?

The easiest way to obtain a SQL Server 2016 executable file (EXE) is to head over to the SQL Server Evaluations page on the official Microsoft website. Make sure to log into your Microsoft account to get the download buttons to appear! 

You can get SQL Server 2016 for free by choosing either the Express or Developer edition. To download Express edition, simply head over to the official Microsoft SQL Server 2016 Express download page. To download the Developer edition you will need to head over to the Visual Studio Dev Essentials website where you’ll need to log in and download SQL Server 2016 from under Downloads. Again, it’s free. If you do not want this hassle, then consider the SQL Server 2016 Express edition, instead. 


  1. Go ahead and double click on the Setup.exe file for the downloaded SQL Server 2016 version to begin the SQL Server installation process. You should find that the SQL Server Installation Center window will pop up (as shown below).

upgrade SQL Server 2008 to 2016


  1. Next, from the left-sidebar select Installation and then choose to Upgrade from a previous version of SQL Server.

upgrade SQL Server 2008 to 2016


  1. Next on the License Terms page, select I accept the license terms

License Terms for SQL Server



  1. On the Global Rules page, you can check to see if all rules are green-ticked with status indicated as Passed. If there is a Failed or Warning rule, click on the link underneath it and resolve the issue from there.  Once you’re done fixing the issue, hit Re-run. Once all is Passed, select Next.

Global Rules for SQL Server


  1. Now, you should find the Microsoft Update page appear. Make sure to check the box for Use Microsoft Update to check for updates (recommended). You may also check or uncheck the checkbox to Include SQL Server product updates on the Product Updates page.

upgrade SQL Server 2008 to 2016


  1. On the Install Setup Files and Install Rules pages,  make sure to go through them and ensure all is Passed. Again, similarly to Step 2, if there is a Failed or Warning rule, click on the link underneath it and resolve the issue from there.  Once you’re done fixing the issue, hit Re-run. Once all is Passed, select Next.
  2. On the Feature Selection page, you can choose the features and installations directories you would like to opt for. The description for the features and directories can be viewed from the top-right part of the page. If you would just like to stick with the default settings, then simply ignore hit Next.

upgrade SQL Server 2008 to 2016


  1. The Feature Rules page is similar to Step 2 & 6. Make sure to check that they’re Passed and fix if there are any Failed or Warning present and proceed to Re-run. Hit Next when done.  

Feature Rules for SQL Server


  1. Now on the Select Instance page, you will need to specify the instance of SQL Server that you wish to upgrade from under Installed instances, which in this case is your SQL Server 2008. Subsequently, on the Instance Configuration page, make sure to specify your own Instance ID for the instance SQL Server.
  2. Lastly, proceed with the rest of the steps and hit Install.

upgrade SQL Server 2008 to 2016


That’s it! You should get a confirmation saying that the upgrade to SQL Server 2016 has completed successfully which you can hit Close

Do make sure to restart your PC. Once your PC restarts go back and test your new SQL Server 2016 to see if it has upgraded and installed successfully. If you’ve backed up all your data, then you should be able to migrate the data now that you’ve upgraded to SQL Server 2016. Microsoft has provided a comprehensive documentation that covers the aspects on both backing up and restoring your SQL Server which you may refer to. 

We hope that this guide has helped upgrade SQL Server 2008 to 2016 for you. If you have questions, please feel free to leave a comment below, and we will love to help you out. ❤


If this guide helped you, please share it. 🙂



  • Jake Kovoor

    Jake is the Editor-in-Chief of Saint and an independent software developer, with a Bachelors in Computer Science from Lancaster University, UK. He loves trying out various tech from the Flipper Zero to coding Raspberry Pis for automation. He started Saint back in 2016, having written over 100 posts, with the sole purpose of creating guides for software that had yet to exist back then to help users navigate around their technical problems.

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