Hi,
We could try manually push the latest patch KB4586845 to the server and the latest does contain new fixes plus the previous monthly update. Before installing KB4586845, we strongly recommend that you install the latest servicing stack update (SSU) KB4566425. SSUs improve the reliability of the update process to mitigate potential issues while installing the Rollup and applying Microsoft security fixes.
As for KB2919355, we can skip it by
- Press Windows key + R, type appwiz.cpl, then press Enter
- Choose “View installed updates”, find KB2919355 and uninstall it.
- Download the "Show or hide updates" troubleshooter. When you click on the download link, you will be prompted to open or save wushowhide.diagcab. Opening wushowhide.diagcab will launch the troubleshooter. Then click Next to proceed and follow the instructions provided by the troubleshooter to hide KB2919355.
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