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In general, Windows Server upgrades are discouraged on EE. &nbsp;How tough would it be to create a 2012R2 VM and configure it to replace the 2008R2 smtp relay server?
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Network Engineer 

kevinhsieh

arnold

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I wouldn't do an in-place upgrade. I really wouldn't do an in-place upgrade if you can't afford to have the relay down for potentially days. I wouldn't want to upgrade to an OS that has less than 2 years of security patches left. Spin up a new 2019, 2016, or Linux VM and get it configured and working, and then give the new VM the original IP address of the 2008R2 server and any needed DNS names/cnames.
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Why dedicate an expensive Server OS license to a mail relay ?<br />
a VM running any linux flavor with postfix as the MTA can be easily setup and configured to route emails to any destination.<br />
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Issue with in-line upgrades as noted you have the success/failure of going from 2008 to 2012.<br />
Then you also have the transition of IIS 7.5 to 8.5<br />
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SMTP component on IIS 7.5 and in IIS 8.5 is under the IIS 6.0 management<br />
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What overlaying functionality is there on this 2008 R2 system?<br />
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A side by side comparison, and verification provides for a smoother, safer transition.<br />
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Can you test in a test lab?<br />
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Get the clone from the current VM in a LAB that mimic the current environment and try it.
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went against suggestions and did a in-place upgrade and successfully upgraded 2008 r2 to 2012 r2 in about 45 min. &nbsp;smtp relay IIS 6.0 worked flawlessly. &nbsp;No issues.
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We have a Win 2008 R2 smtp relay server (configured in IIS 6.0 Manager). &nbsp;We need to upgrade it to 2012 R2. &nbsp;If I do this in-place upgrade will it break smtp relay and will I need to reconfigure it within 2012 R2?
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We have a Win 2008 R2 smtp relay server (configured in IIS 6.0 Manager).  We need to upgrade it to 2012 R2.  If I do this in-place upgrade will it break smtp relay and will I need to reconfigure it within 2012 R2?

smtp relay server in-place upgrade from 2008 to 2012

Windows Server 2012 is the server version of Windows 8 and the successor to Windows Server 2008 R2. Windows Server 2012 is the first version of Windows Server to have no support for Itanium-based computers since Windows NT 4.0. Windows Server 2012, now in its second release (Windows Server 2012 Release 2) includes Foundation, Essentials, Standard and Datacenter, and does not support IA-32 or IA-64 processors.

Windows Server 2012

Windows Server 2008 and Windows Server 2008 R2, based on the Microsoft Vista codebase, is the last 32-bit server operating system released by Microsoft. It has a number of versions, including including Foundation, Standard, Enterprise, Datacenter, Web, HPC Server, Itanium and Storage; new features included server core installation and Hyper-V.