Granting my Windows installations one last round of updates, I noticed that Windows Update would not let me install KB4516655.
Hopping around through the internets forums to figure out how to solve the situation, I found that the security update needed another update which is probably not on the list of dependencies of the update package:
KB4474419 had already been installed
KB4490628 this one was missing (and once linked correctly, and once linked to a different KB 4512506 here, which I did not immediately recognize)
KB4512506 (Monthly Rollup August 2019)
After applying those updates manually, KB4516655 could be installed, allowing the succeding rollups 2019-09 and 2019-12.
Of course, the WindowsUpdate.log file does not indicate, WHY things go wrong:
Misc =========== Logging initialized (build: 7.6.7601.24085, tz: +0100) =========== Misc = Process: C:\Windows\system32\wuauclt.exe Misc = Module: C:\Windows\system32\wuaueng.dll Handler ::::::::::::: Handler :: START :: Handler: CBS Install Handler ::::::::: Handler Starting install of CBS update 7CC120FB-9672-4AE5-BBA6-90651174A717 Handler CBS package identity: Package_for_KB4516655~31bf3856ad364e35~amd64~~6.1.1.1 Handler Installing self-contained with source=C:\Windows\SoftwareDistribution\Download\4009abf0458aef77b1e27406d1395603\Windows6.1-KB4516655-x64.cab, workingdir=C:\Windows\SoftwareDistribution\Download\4009abf0458aef77b1e27406d1395603\inst Report REPORT EVENT: {0478CEF6-1B68-4959-A8F2-5DD5AD90DAFA} 2020-01-11 11:23:25:458+0100 1 181 101 {271A1B3A-DD7A-4D8A-94E1-9E44BFC9149F} 501 0 wusa Success Content Install Installation Started: Windows successfully started the following update: Sicherheitsupdate für Windows (KB4516655) Handler FATAL: CBS called Error with 0x80092004, Handler FATAL: Completed install of CBS update with type=0, requiresReboot=0, installerError=1, hr=0x80092004 Handler ::::::::: Handler :: END :: Handler: CBS Install Handler :::::::::::::
And the Windows Update “Help” is just as unhelpful.