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Ray Bakker
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ASP.NET, Windows 2012, Windows 2019, IIS 8.5, IIS 10,

We would like to perform an in place upgrade of Windows server 2012 R2 running IIS 8.5 to Windows 2019 and  IIS 10. We are currently running ASP.NET applications with Framework 4.6.2. If anyone is aware of any issues, things to be aware of. We are using Telerik Ajax controls. 

ASP.NETWindows OSWindows Server 2012Windows Server 2019* iis 10

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Last Comment

8/22/2022 - Mon

Is this a physical or virtual environments?

You are skipping two os versions.

The .net on2019 is 4.7 if not mistaken.

Best case scenario, the upgrade goes through and  you are all set.
The alternative is OS changes, iis configuration,, etc.
Do you gave a good back up, test you test restored in a test lan to make sure it works?

A clean install if VM, could be a better approach ...that includes the flexibility of managing your time..
Ray Bakker


Thank you for responding. We are using VMs.
Current Environment:
Windows 2012 VM
IIS 8.5
Framework 4.6.2
Crystal Report Viewer: 13.4

Moving to :
NEW Windows 2019 Vm
IIS 10
Framework 4.6.2 (hopefully)
Crystal Report Viewer: 13.4 (hopefully)

We are currently bringing up a NEW Windows 2019 VM and will test if it works and want to publish our app to the new 2019 server. Is anyone aware of any issues?

The 2019 cobfiguration is much more granular as compared to the 2012 in a similar way as the iis7 compared to 8.5.

Application pool, and which features settings you need for the site.
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William Peck
Ray Bakker

The approach we were discussing was to spin up a new Windows 2019, Setup IIS 10  comparing features on the old server and add accordingly. then publish the applications to the new server. I did however find this:

Synchronize IIS | Microsoft Docs  Anyone with experience using this?
Thanks again.

You could try, but I think this was helpful if you went from 6 or 7 to what you have now, not sure

The newer option might be better suited.

You can test different approaches.

the tool is supposed to simplify what you said your implementation plan is.
Ray Bakker

So we spun up a new VM server and published a couple of apps to it. So far so good. One issue with Crystal Reports runtime engine. Going to post a new question regarding the runtime and windows server 2019.
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Ray Bakker

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This was the suggestion I made in my first comment.