2012 R2 to 2019 Upgrade Fails: What Should I Do?

Can you upgrade Windows Server 2012 R2 to 2019?

Yes, you can upgrade Windows Server 2012 R2 to Windows Server 2019. In the provided diagram, it illustrates that in-place upgrades are supported between any two operating systems that are linearly connected.

The in-place upgrade method allows for a direct transition from an older system to a newer one, preserving hardware, settings, server roles, and data without wiping the server. This approach is considered the easiest when upgrading from Server 2012 R2 to 2019.

However, if you're upgrading from Windows Server 2012 to 2019, you'll first need to perform an in-place upgrade to 2016 and then upgrade from 2016 to 2019. So I suppose this is one possible reason that accounts for 2012 R2 to 2019 upgrade fails.

Alternatively, a clean install of 2019 is possible, but it involves overwriting the existing operating system, requiring advanced backup measures to prevent data loss.

Error: upgrade Windows 2012 R2 to 2019 failed

“2012 R2 to 2019 upgrade fails” means that you encountered a failure while trying to upgrade Windows Server 2012 R2 to Windows Server 2019. This can happen at any stage of the upgrade process and can fail for a number of reasons. Some common reasons for failure include：

♥Corrupt installation media: If the installation media is corrupt or has missing files, the upgrade process may not continue.
✍Fix: As for this issue, you can create a new Server 2019 installation media and try to upgrade again.
♥Prior operating system issues: If there are unresolved issues on Windows Server 2012 R2, this may prevent the upgrade process.
✍Fix: You can run the Troubleshooter or boot in the safe mode to see what's wrong with your computer.
♥Security Software Interference: Sometimes, security software, such as an antivirus program, can interfere with the upgrade process.
✍Fix: Simply disable the security software temporarily.
♥Network Issues: If you lose your network connection during the upgrade process, the upgrade may fail.
✍Fix: Make sure a secure and stable network connection
♥System configuration issues: Some specific system configurations may not be compatible with Windows Server 2019 and may need to be adjusted.
✍Fix:  Make sure the hardware requirement is satisfied.
♥Upgrade process interruption: If any unexpected interruption occurs during the upgrade process, such as a system crash or power failure, the upgrade may fail.

Additionally, you can try an intermediate upgrade. How? Try to perform an upgrade from Windows Server R2 to 2016, then from Windows Server 2016 to Windows Server 2019.

Suggestion: backup Windows Server in case of any data loss

Honestly, no matter when you should consider taking a full backup of your computer. For example, the time when you decide to upgrade your computer from Windows Server 2012 R2 to 2019. Or you need to troubleshoot some upgrade issues like upgrade Windows 2012 R2 to 2019 failed. Being aware of making a regular backup is always a good habit to safeguard your data.

There are a lot of backup options for you, one outstanding choice is AOMEI Backupper Server. This software is designed for server users with a user-friendly interface and settings. You can resort to it to backup your data when Windows Server 2012 end of life as well.

★Wide applicability: It supports Windows Server 2003, 2008, 2011, 2012, 2016, 2019, 2022 (including R2), Windows SBS 2003, 2008, 2011 and Windows XP, Vista, 7, 8, 8.1, 10, 11.
★Destination flexibility: No matter whether you want to upgrade Windows Server 2012 r2 to 2019, 2016 to 2019 or 2022, you could use this software to backup the server to internal/external hard drive, NAS, network share, cloud service, etc.
★Complete support: It includes file/folder/partition/disk/system/cloud backup & restore with many useful options. For instance, you can create scheduled incremental or different backup, set up a retention policy to auto-delete older backups, restore system images to different hardware, etc.
★Additional feature: Moreover, it contains Sync features to copy your data with the original format and structure, Clone features to duplicate hard drive and therefore migrate Windows Server to SSD.

Now download this software and follow the below instruction to backup your computer.

Step 1. Launch AOMEI Backupper. Click on Backup and select System Backup.

✍Tips: This software also offers you wonderful cloud storage service. It enables you to backup folders to AOMEI Cloud, a cloud drive released by AOMEI Tech, which offers 1TB of free cloud storage from the time you sign up for an AOMEI account until 15 days.

Step 2. It will select the necessary system partition(s) by default. You just need to choose the destination path to store the backup files.

Step 3. (Optional) Click Schedule Backup in the left lower bottom, and then choose Enable Schedule Backup to set the frequency of the system backup as you like.

Step 4. Confirm the operations and click Start Backup to backup Windows Server.

Conclusion

2012 R2 to 2019 upgrade fails can be a result of various reasons. Here we list some, you can check them one by one. One possible solutions is perform intermediate in-place upgrade from Windows Server 2012 R2 to 2016, then from 2016 tp 2019.

Can you upgrade from server 2012 to 2019? The answer is also affirmative. You can refer to upgrade Windows Server 2012 r2 to 2019 to know 2 ways to realize successful upgrade.