Windows Server Upgrade Path
Microsoft has a simple step-by-step guidance for modernizing Windows Server. Please refer the link: https://www.microsoft.com/upgradecenter
In this article a table has been prepared based on Microsoft's guide.
| Product | Server 2008 R2 SP1 | Server 2012 | Server 2012 R2 | Server 2016 | Server 2019 |
1 | Windows Server 2008 R2 | Direct | Direct | Direct | Yes | Yes |
2 | Windows Server 2008 R2 SP1 | - | Direct | Direct | Yes | Yes |
3 | Windows Server 2012 | X | - | Direct | Direct | Yes |
4 | Windows Server 2012 R2 | X | X | - | Direct | Yes |
5 | Windows Server 2016 | X | X | X | - | Direct |
7 | Windows Server 2019 | X | X | X | X | - |
Direct - Can be upgraded directly with one setup
Yes - Can be upgraded by consecutive upgrade processes
Note
During OS version upgrade, the OS edition must remain same or can be upgraded. The edition can not be downgraded by in-place installation. Example: Windows Server 2008 R2 SP1 Standard can upgrade to Windows Server 2012 Standard or Datacenter edition.
Upgrade path from Windows Server 2008 is not tested by Ginesys Team. You may contact your server administrator for this. A reference blog link is mentioned in Reference section.
References: