Windows 10 Cumulative Update KB4494441 Installing Twice for Some Users

The most recent cumulative update for Windows 10 October 2018 Update, or version 1809, installs twice on some devices.

Windows 10 cumulative update KB4494441 was published as part of the May 2019 Patch Tuesday, bringing both security and non-security improvements to devices already updated to version 1809.

The update comes with four different known issues, all of them borrowed from the previous patches for Windows 10, but none of them pointing to any installation problems.

But as discussed in this reddit thread, Windows 10 cumulative update KB4494441 installs twice on a number of devices for a reason that’s yet to be determined.

By the looks of things, the behavior is the same in all cases. KB4494441 is first offered to Windows 10 October 2018 Update devices via Windows Update, with a reboot then required to complete the installation. Despite the machine being restarted, KB4494441 is then re-offered for a second time on Windows Update, once again with a reboot required to finalize the update.

After the second system restarted, KB4494441 appears to be installed correctly, with the OS build number increased to 17763.503. After the first install, the OS build numbers continues to be 17763.475.

Bug acknowledged

Microsoft has acknowledged the problem and says that “Windows 10, version 1809 Update Tuesday update may install twice,” adding that it is currently investigating and will provide an update when available.

Fortunately, the installation of cumulative update KB4494441 doesn’t seem to fail on any devices, so despite needing a second attempt to complete the install, everything appears to be working correctly.

To check if KB4494441 installed correctly on your device, click the Start menu and type winver to verify the OS build number. If you’re currently running 17763.503, everything worked well. Also, in the update history page, you should see the following entry: