On two of ‘my’ Windows Server 2008 r2, I had an update (KB2992611) that failed with the following error code: 0x80244019

In my investigations, I found the following procedure to fix the problem (in both cases).

The Solution

Open an Administrative Command Prompt.

As a first step, you have to stop Shadow Copy & Windows Update services, by the following commands:

net stop wuauserv
net stop bits

Then delete any content from the following system folder:

%systemroot%\softwaredistribution

Then type the following commands:

net start bits
net start wuauserv
gpupdate /force
wuauclt /resetauthorization /detectnow
wuauclt /reportnow

and reboot.

Once ready, restart Windows Update again, and this time the update should be installed without any problem.