I've got several web servers servers running Server 2008r2 SP2 Standard with SQL Server 2014. What is the best practice / easiest in-place upgrade path to get to Windows Server 2016?

In testing I'm only able to upgrade from 2008r2 to 2012 and then upgrade again from 2012 to 2016. We've got a decent amount of configuration done on these and quite a few websites running on them. With that in mind having to upgrade twice isn't ideal due to the downtime involved. Is there any way around this? (change license keys or some other solution?)


  • Are you hardware-instance limited? Can you build new machines side-by-side and migrate rather than upgrade? If you're running virtual I'd look into building new SQL servers and move the DBs, then move the web services over to new hosts. – music2myear Mar 15 '17 at 21:51
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    @music2myear Yep, that's we decided on as the best approach. Turns out there's a neat tool to migrate IIS websites and a decent guide with different SQL migration approaches: iis.net/downloads/community/2013/04/… and sqlsolutionsgroup.com/migrate-sql-server – cvocvo Mar 15 '17 at 21:58
  • I've posted this as an answer below. If you'd be so good as to mark it as the correct choice I'd appreciated it. – music2myear Mar 15 '17 at 22:03

If you must stay with the same hardware/machines, then a two-step upgrade is your only option:

2008 to 2012, then 2012 to 2016.

But, if you have a virtual infrastructure or can use additional hardware, you can treat this as a migration rather than an upgrade.

Build new SQL servers and new IIS hosts, and then migrate the applications rather than upgrade the OSes.

  • Thanks for the mark. To the downvoters: Could you explain yourself? What about this is wrong, how can it be improved? – music2myear Mar 16 '17 at 16:09

I'm afraid not as there is no in-place upgrade path from 2008 to 2016. At least not from Microsoft. Not sure if there're 3rd party utilities out there to achieve this.

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