We have a couple of vm servers still running Windows Server 2003 R2 Enterprise 32bit.
There are many vulnerabilities and some of the ways of fixing the problem will be upgrading to a higher version of Windows Server and IIS.
(Plus Microsoft stopped supporting Server 2003.)
I think we will have to go from 2003 to 2008, 2008 to 2012, and then 2012 to 2016? Is this the only way? or there are other better approach to upgrade to newer version?
And I guess data and configuration will need to re-do manually?
Best Answer
It's 32-bit. It can't be upgraded. Server 2008 R2 and newer only come in 64-bit versions. There is no upgrade path from 32-bit to 64-bit.
In addition, this would be like trying to upgrade Windows XP to Vista, to Win 7, to Win 8, to Win 10. I highly doubt you would attempt that on a home computer, so why consider it for a production server?
Instead, come up with a migration strategy that involves building out 1 or more 2016 servers and migrating domain roles, server roles, applications and files over.
You also need to consider replacing the hardware, as anything running server 2003 is beyond end of life and highly unlikely to support a newer OS very well if at all.