Upgrade SQL server from 2005 to 2014 along with OS upgrade from MS Server 2003 to 2012 r2

We have SQL Server 2005 running on Windows Server 2003. I am looking to upgrade both the OS to Server 2012 r2 and Sql to SQL 2014 Ent, is there any specific order this should be done in and if so what is that order? SQL 2014 Upgrade Advisor
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Vitor MontalvãoMSSQL Senior EngineerCommented:
SQL Server 2014 doesn't run on Windows Server 2003 so you'll always need to upgrade the OS first.
But if you're using old hardware, I'll recommend you to buy a new server or try to install on a virtual machine and then you execute a side-by-side migration of the database instead of an in-place upgrade.

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LemonCalvinAuthor Commented:
Will the side-by-side retain custom settings such as an in-place upgrade?
Vitor MontalvãoMSSQL Senior EngineerCommented:
What kind of custom settings?
If they are stored in the database, when you migrate the database it will take the custom settings with the database.
If you're talking about other type of custom settings, please exemplify.
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LemonCalvinAuthor Commented:
Cool! I didn't know how much of a difference in-place -vs- side-by-side was... if at all. I was under the assumption that one brought along users, odbc, settings etc. and the other one didn't.
LemonCalvinAuthor Commented:
Thank you for the info, I am in the process of preparing to do a side-by-side upgrade. This should be interesting and not as painful as I initially thought. Thanks again!
Vitor MontalvãoMSSQL Senior EngineerCommented:
Your welcome.
Just don't format the old server before the new one is up and running for at least a couple of weeks.
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Windows Server 2012

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