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Running a fresh install of High Sierra 10.13.6 in VB 5.2.24. Got the High Sierra install by downloading from the Apple Store several months back. (incidentally, I've notice the store no longer has Sierra or High Sierra in the 'purchased' section)

After the usual trickery to get 10.13 installed I was able to boot successfully to a desktop. Ran Apple Store and updated Safari and iTunes. Updates required a restart, and after the restart they applied successfully. Next update was the most recent security update 2019-001 for 10.13.6. It downloads and successfully restarts to the installer. Take a couple minutes, says 'Installing updates', then boots back to the desktop. Run Apple Store again and the same update appears. In system profiler System Version is listed as 17G65. On my host, which has 2019-001 installed, the system version says 17G5019, so it appears the update didn't install on the guest. Repeating the process only ends in the same result. Incidentally, I also tried using Same thing, it appears to install, but after reboot system version is unchanged.

Any ideas?

Ok, very weird. I think I fixed it, here's how.

Per something I saw elsewhere in the forums about a different security update that wouldn't work, I ran The command line downloads the update but doesn't install. I manually restarted, then pressed keys on the keyboard at reboot to drop into the EFI controller. I opened Boot Maintenance Manager -> Boot From File -> Selected the 2nd item /HD(2,GPT....) -> MacOS install data -> locked -> boot -> boot.efi. It booted and says 'Installing MacOS' as though its reinstalling the whole OS, it even estimated 45 minutes. After just a few minutes it finished, rebooted and bam, it's fully updated.

Posting in case someone else has this issue.

Thank you for the solution. It may come in handy in the future...

Thank you for the tip, it worked perfectly for me on Virtual Box 6.0.4 running on an iMac 14,3. May be just a tip for beginners like me: press the fn/F12 key (or just F12 if "use F1, F2, etc. keys as standard function keys" is ticked in the Keyboard System Preferences) immediately after restart to get into the EFI reboot.

ptisuisse wrote:press the fn/F12 key immediately after restart to get into the EFI reboot.

Try pressing the AnyKey™
Works as well...

Hello Folks:
I have a related problem I think. I'm running VBox 6.0.4 and hosting on a Mid 2011 27"iMac running 10.13.6 and my guest macOS 10.13.6 also can't seem to recover from installing the SECURITY UPDATE 2019-001. I F12 to get to the boot menu and choose the EFI boot file in the OS updates folder that gets installed but then it doesn't ever install the update and reboot back into a patched system again. I've got several snapshots I've taken along the way and can step back to just before the Security Update starts to download and install. I've done that several times and run through the process again but it always results in the same failure.
Can anyone list the steps they've taken to successfully perform this patch?
Thanks,
- Scott Beach in Toronto