I need to upgrade and migrate SQL Server, SSRS, SSIS to the newest OS version and SQL Server version.

Server OS is currently 2008 R2 with SQL Server 2008 R2 Ent. installed.

My original plan was to do in place upgrades and then migrate to new server OS. It sounds like SQL Server 2017 is not supported on 2008 R2, so I'm not sure whether or not this is an option.

What is the best migration/upgrade path for server OS upgrade and SQL Server version upgrade?

Windows Server 2008 R2 and SQL Server 2008 R2 Ent -> Windows Server 2019 and SQL Server 2017 Ent.

  • You need to have 2012 or higher server OS to install/upgrade to MS SQL Server 2016 and higher. I have upgraded in place our SQL Server 2008 R2 to SQL Server 2017 recently, installing SP3 on SQL Server 2008 R2 before. But the server OS has already been 2012. Jul 9, 2019 at 6:11

2 Answers 2


As always it depends...

Whats the complexity of your instance? How many SSIS packages / SSRS reports do you need to move along? How much time do you have to perform this upgrade? Whats your maintenance windows within which the service can be inaccessible? And many many more...

Before you start looking for any kind of answers I would recommend to create an inventory of what exactly do you have. Very helpful thing is to add source control over your entire DB server. With that in hand you can "mask it a bit" and then share with the community - much higher chances for good answers.



  1. first upgrade to MS SQL Server 2014 with the latest updates

  2. upgrade Windows Server to version 2019

  3. update MS SQL Server to 2016 or 2017 version

I don’t put the 2017 version, and there were a lot of problems including administration. Upgrade MS SQL Server to 2016, and then wait for the release of MS SQL Server 2019

  • 3
    There will never be any such thing as SQL Server 2019 SP1, since Microsoft has completely changed the servicing model (where is 2017 SP1?). Please stop perpetuating the myth that you have to wait for a service pack to use a product. Jul 9, 2019 at 1:45
  • The idea is to use only proven solutions on production. Therefore, it is better not to rush to install the latest updates, especially for MS SQL Server Aug 19, 2019 at 4:54
  • This is nonsense. Microsoft switched from service packs to cumulative updates. They are just as tested as service packs always were. Please stop fear-mongering. Aug 19, 2019 at 11:34
  • No need to trust marketing. It is important to check whether the product really has no problems. Microsoft has repeatedly shown that there are problems with updating or with the release of a new product. For databases, this is especially critical. Therefore, I repeat, it is important to take time-tested decisions, and not risk business. Aug 20, 2019 at 12:22
  • So you say you trust SQL Server 2016, don't trust 2017, but will rush to install 2019? Again, your logic makes no sense to me (and my opinion does not come from marketing). If you don't trust Microsoft software, use something else, don't try to scare people. You know that there will never be a service pack for SQL Server 2017 or 2019, right? Think about that for a minute in the context of your statements. 2017 has been in production for two years, what are these "there were a lot of problems"? Aug 20, 2019 at 13:04

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