Upgrading Windows Server 2008R2 File Server to Windows Server 2016

The user organization has two Windows Server 2008 R2 file servers that have been joined to the domain. There are two other domain servers, each running the Windows Server 2016 operating system. Because Windows Server 2008 and 2008 R2 technical support will end on January 14, 2020, the user wants to upgrade these two Windows Server 2008 R2 file servers to Windows Server 2016. These two file servers have shared folders with many folder permission configurations. Users require that the original user permission configurations be retained after upgrading to Windows Server 2016.

Windows Server 2008 R2 does not support direct upgrade from Windows Server 2008 R2 to Windows Server 2016. You need to upgrade Windows Server 2008 R2 to Windows Server 2012 R2 first, and then upgrade to Windows Server 2016. This can be seen in "Windows Server Installation and Upgrade", the link page is:
https://docs.microsoft.com/zh-cn/windows-server/get-started/installation-and-upgrade. The following is a reproduction of the upgrade process.

1 If you upgrade directly to 2016, user settings will not be retained

The current version is Windows Server 2008 R2 SP1, as shown in Figure 1.

Figure 1 Current system version

Enter the Windows graphical interface and run the Windows Server 2016 installation program, as shown in Figure 2.

Figure 2 Select the version to install

In the Choose what to keep dialog box, you cannot select Keep personal files and apps, as shown in Figure 3.

Figure 3 Unable to save settings

Exiting the installer because apps and settings cannot be preserved.

2 Upgrading to Windows Server 2012 R2

Reload the Windows Server 2012 R2 installation CD and run the installation program. Select Windows Server 2012 R2, as shown in Figure 4.

Figure 4 Installing Windows Server 2012 R2

In the "Which type of installation do you want to perform" dialog box, select "Upgrade: Install Windows and keep your files, devices, and applications", as shown in Figure 5.

Figure 5 Upgrade

Then start the upgrade installation, as shown in Figure 6.

Figure 6 Upgrade installation

After the upgrade is complete, enter the system, as shown in Figure 7.

Figure 7 Upgrading to Windows Server 2012 R2

3 Upgrade again to Windows Server 2016

Then load the Windows Server 2016 installer and install Windows Server 2016, as shown in Figure 8.

Figure 8 Installing Windows Server 2016

In Choose what to keep, select Keep personal files and apps, as shown in Figure 9.

Figure 9: Keep personal files and apps

Then start the installation and upgrade of Windows Server 2016. After the installation is completed, it is shown in Figure 10.

Figure 10 Upgrade completed

With a "mid-cycle" upgrade to Windows Server 2012 R2, user settings and configurations are preserved.

Use the same method and steps to upgrade another Windows Server 2008 R2 in the network to Windows Server 2016. These will not be introduced here.