With Microsoft changing their update process to cumulative updates, KB2919355 may not install as part of the normal Windows Update process. Here's how to manually install this KB.

The instructions here are from https://www.microsoft.co.../details.aspx?id=42334.

Step 1: Download KB2919355 and associated updates
Go to https://www.microsoft.co...d/details.aspx?id=42334 and download all the updates into a single folder.

With the exception of the clearcompressionflag executable these updates will all say Windows 8.1.

Step 2: Download prerequsites
Download KB 2919442 from http://www.microsoft.com...firmation.aspx?id=42153 and put it in the same folder.

This update will say Windows 8.1.

Step 3: Install Windows Server 2012 R2
Install and activate Windows Server 2012 R2 from your media/iso image.

Step 4: Install KB2919442 and KB2919355 and restart
Install clearcompressionflag.exe
Install KB2919442
Install KB2919355. This is a long installation.
Restart your server when requested.

Step 5: Verify KB2919442 and KB2919355
Open Windows Update and look at the Update History view. The two updates up just installed should be it.

Step 6: Install remaining updates in the following order
Install KB2932046 and restart
Install KB2959977 and restart
Install KB2937592
Install KB2938439 and restart
Install KB2934018 and restart

Step 7: Verify all updates are installed
Open Windows Update and view the update history to ensure all updates are installed.

Once you've done the steps above you can continue configuring your server. Some services, such as SQL Server 2016 require KB2919355 be installed. Unfortunately the new cumulative update model doesn't install this update, which contains changes to how Windows Update operates.