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When Is an In-place Windows Server OS Upgrade Required?

Jerry Zwolen

Jul 13 2021

3 min read

Server upgrades are an essential part of growing with technology. Not only is the hardware more capable, more robust, and cheaper, but the Operating Systems are more advanced as well. More features, more security, and more support. While most IT professionals would recommend a full migration to a new Windows server/OS, there are some instances when an in-place upgrade can be required.

I recently had a client ask for a server upgrade on a single server. The reason for the upgrade was to upgrade aging vendor software. The software in question was going from version 10 to version 2019, a 5-version jump. Unfortunately, the Server OS (in this case, Server 2012 R2) was no longer supported by the current software version. To complicate matters further, this particular server was a physical server hosted at a third-party data center. I engaged the hosting company, but in this particular case, even the hosting company could not provide any form of “upgrade” without moving to a completely new service offering. As usual, they needed the upgrade ASAP to provide new industry product offerings.

While I firmly believe most people steer away from an in-place upgrade, I’ve had nothing but success in the past. The customer was adamant about getting this done immediately, so I proceeded with the upgrade. Please follow the MS upgrade compatibility matrix as needed. In my case, the client was on Server 2012 R2, so I was able to upgrade directly to Server 2019. Download the installation ISO as you would for any server installation, and mount it into the current OS.

Installing the In-place Server OS Upgrade

As with any OS installation or upgrade, there are just a few choices you’ll need to make. Once you run setup.exe, you’ll be prompted to choose which version you’d like to install. I chose the 2019 standard (interactive version). Next, I chose to “keep your files” during the installation. This will ensure the install is an upgrade and not a full re-install. I also initially chose to skip the downloading updates, as I wanted this install to complete as quickly as possible. After clicking continue, you’ll see the usual installation progress percentage/bar.

Once completed, the server will reboot and you’ll be logging into your new OS version. Remember to check the device manager to make sure you have drivers installed. I also immediately ran a few courses of Windows Updates with reboots to fully patch the OS. Once the upgrade is complete, you can move into upgrading your software as necessary.

Have any questions about an in-place Windows Server OS upgrade or a full migration? Please contact us at any time!

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About the Author

Jerry Zwolen

Jerry Zwolen is a senior network consultant in IT consulting and technology services. He has over 15 years of experience and serves a range of industries. His expertise includes Microsoft HyperV, Microsoft Office 365, IT consulting, VMware Hypervisor and Meraki Wireless. Jerry’s certifications include Microsoft MCSA, Microsoft MSCE and Cisco CCNA. When he’s not working, Jerry is spending time with his very grumpy, very old cat.