Windows Server 2012 goes into update loop

[German]Today I want to bring up again another issue regarding the update behavior of Windows Server 2012 (default, not R2). Some machines running Windows Server 2012 have been in a pending update loop since early November 2019. Now some workarounds has been found.

An old blog post from November 2019

I had already addressed the topic after a reader's tip in the blog post Pending Pending Update Issue with Windows Server 2012 Standard at the beginning of November 2019. The problem: After installing the updates, some Windows Server 2012 goes into a restart loop, where the update process shows the status "Pending restart". This status is not vanishing, i.e. the updates are installed repeatedly or retain the status "Pending restart" even after a restart.

(Click to zoom)

In the article, the blog reader had suspected that the "Desktop Experience" feature might be involved in this problem.

Restart loops for Windows Server 2012

In Microsoft's Technet Forum there is now this thread in which a person affected describes his observation.

Windows Server 2012 stuck in reboot loop "Configuring Updates: Stage 2 of 4

After installing November monthly updates from WSUS server, about 80% of 2012 Servers stuck in loop.

Server (VMware VM) launches a stage 2 of 4 again, then it goes shutdown of services and reboot.

All Servers restored from backup. Any updates tried to install cause loop.

Previous monthly updates uninstalling cause loop. Renaming of SoftwareDistribution, rescanning of updates and installing cause loop.

Last monthly installation has been made without any problems on all Servers.

All updates show the same behavior on the affected servers that the update cannot be completed successfully. Currently another administrator has posted this comment in the blog. He has this on about 20 machines running Windows Server 2012 (partly virtualized). Microsoft's advice to perform an in-place upgrade for repair installation is not helpful. Programs and data are lost.

Meanwhile, a reader of my blog has referred to this article, where the problem is also described. A few days ago Woody Leonhard also posted this article on askwoody.com. It also describes a reboot loop on Windows Server 2012 following the installation of the Servicing Stack Update (KB4523208). The article goes back to this report by an administrator. He observed the mentioned restart loop on different Windows Server 2012 systems with SSU KB4523208 installed. However, only 6 of 75 servers were affected (bar metal and virtual servers).

Tip: How to avoid the Update Install loop

German blog reader Marco wrote within a comment, that manually force Windows Server 2012 to install the Servicing Stack Updates (SSU) first, before the other updates are scheduled for in installation helps avoid the issue.

Furthermore I was successful with most Win2012 servers after these experiences, if I had installed strictly as first the current "Service Stack" update.

If the latest SSU is installed, at least known (Microsoft) problems that prevent a successful update installation will be fixed. The description of Servicing Stack Update KB4523208 in Microsoft Update Catalog says, that the patch need to be installed exklusive.

Within the Technet forum thread user Sasidhar Konduru reports that they identified the Malicious Software Removal Tool (MSRT), update KB890830, as the cause of the installation loop. If KB890830 was installed together with other updates, the installation loop occurred. Once the MSRT was blocked in WSUS for distribution, the update installations went through.

If you are caught in an update installation loop, the following solutions may help.

Solution #1: Booting in Safe Mode

Within this post, the person concerned writes that he was able to solve the problem by booting in the safe mode. In Safe Mode, the restart loop was interrupted and the update was successfully installed. Using the safe mode to fix the restart loop is also mentioned as a solution in the Technet forum and in this article.

In safe mode, only basic Windows functions with a limited set of files and drivers are executed. Safe mode is described in this Microsoft document.

Solution #1: Launch Trusted Installer Service

Other German blog readers commented (here and here) that the following solution helps:

• Initiate installation and the Windows Modules Installer service to Automatic before restarting.
• The servers then restart several times (always shows the same phase, don't let it irritate you) and then the updates are installed.

Especially the installation seems to take a long time and requires several reboots. Maybe it will help.