I ran KB4494441 update here on two different computers and got the same results. After clicking on "Check for Updates" in "Settings-Updates and Security" and allowing things to proceed, detect the various updates, download, install and restart, both computers showed the KB4494441 update as installing successfully. But when I clicked on the "Check for Updates" button again, the cumulative update came up again, downloaded again, installed again, and required a restart again. The second time, the "installing" process took longer to finish on both computers but finished correctly, restarted correctly and everything went fine. Luckily, on both computers, the second time was a charm and the update installed correctly and was not dtected a third time. When I "Viewed update history", the update showed as installed twice with the (2) listed at the right side of the listed update.
Others are seeing the same thing. See the link below:
I'm just posting this so members will know a second "Check for Updates" and install should allow the update to install correctly. At least I hope so.
Hope this helps.
Microsoft released new security updates today. Both Critical and Important Updates have been released. Updates include those for Microsoft Windows, Microsoft Edge, ASP Net, NET Framework, Visual Studio, SQL Studio, Internet Explorer, ChakraCore, Adobe Flash, and others.
Microsoft Security Updates for May 14, 2019
Microsoft also released an updated version of the Microsoft Windows Malicious Software Removal Tool on Windows Update, Microsoft Update, Windows Server Update Services, and the Download Center.
May 2019 Security Update Release Notes
In addition, Microsoft released a number of updates for Microsoft Office in the link below.
May 2019 updates for Microsoft Office
Hope this helps.