Risks involved in upgrading to SQL Server 2008 R2

That's a really big question so let's break it up a bit.

What can I do in advance?

Start with some required reading.

  • 2008 R2 Backwards Compatibility
  • 2008 Backwards Compatibility

These links have links to further information such as

  • Deprecated SQL Server Features
  • Discontinued SQL Server Features
  • Breaking Changes
  • Behavior Changes to SQL Server Features

Read each of them to see what major stuff is changing. Pay particular attention to features you are using.

In addition you should use the Upgrade Advisor. It checks for installed components and identifies those you will need to fix either before or after the install.

In-Place vs Side-by-side

Lots of pro's and con's here on both sides.



  • MUCH easier. All of your configurations stay the same for example. Also the connection strings for your applications probably won't need to be changed.
  • Cheaper. No second set of hardware required.


  • Backout is difficult to impossible. If something goes wrong you are going to have to power through and finish because backout involves creating a whole new server and reinstalling SQL then restoring backups of your tables.


Basically the pros & cons are the opposite of In place.


  • Safer - If something goes wrong you kill the new version and just continue on with the old one. Then you can try again later.


  • It's more expensive because you have to create a new set of instances probably on new servers.
  • It's more difficult because you have to change connection strings, make sure all of your configurations are the same, etc.

Now you can mitigate the expense of the side-by-side by creating a new instance on the same server, moving everything to it, then uninstalling the old instance. It works and depending on your situation might be the best idea.

General Risk

Honestly the move from 2005 - 2008 R2 isn't that bad. It's nothing compared to 2000 - 2005 or 2008 R2 - 2012 (mostly SSIS changes). I'd say with careful planning and reading you should be in good shape.

So my question here is not how, rather will like to know the risk involved or any pre-checks that can be done before planning this upgrade?

You should run upgrade advisor and address the issues reported by it before migrating.

Refer to my answer for an extensive list of pre and post upgrade steps.

SQL server which needs to be upgraded from version 2005 to 2008R2

You are picking the a path where you will be back to square 1 (since within 3 years, you will have to upgrade again). See below table

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will Inplace upgrade be a better plan or side by side for this migration/upgradation?

Based on my experience, I would suggest you to do a side-by-side migration since you are getting new OS and SQL version. This is a much cleaner approach since you will have your old servers still around, just in case you want to failback. Refer to : Are SQL Server in-place upgrades as ill advised as they used to be?. Dont get me wrong when I suggest a side-by-side migration, its just a safer side when it comes to rollback.