Tax Time OSX Upgrades

It's the time of year that in the US people have to figure out whether or not they owe olde Uncle Sam. Unfortunately, as a linux user, most personal tax software won't run or isn't supported. Fortunately, several years ago I made a Mac OSX VM just for tax time. Unfortunately, this year Mac OS High Sierra is no longer supported by TurboTax. So, I took this snowy new England day to upgrade from High Sierra to Mojave.

1. Take a snapshot/backup of the VM


2. Download a full copy of Mac OS Mojave in your VM. Dosdude1's patcher is great for this.


3. Make an iso of the installer, then copy it to your host machine.


4. Start the install process, expect it to not continue the installer after reboot.


5. Reboot and swear repeatedly as it fails to recognize the Esc key for the 20th time to get into the EFI Menu.


6. Go into the EFI shell, navigate to \macOS Install Data\Locked Files\Boot Files\


7. Run the boot.efi


8. Twiddle your thumbs or listen to a podcast while waiting for Mojave to Actually install..


9. Curse some more when upgrade fails...


10. Figure out the error about being unable to delete file vm due to permissions is a red herring for the installer being unable to update UEFI settings correctly due to the root partition now being APFS


11. Blow off some steam in giant stompy robots


12. Find a usable shim online to boot the upgrade


13. Complete the upgrade, remove extra disks and realize you have to boot from the installation CD and edit the EFI partition contents for a longer term fix


14. Remember belatedly that even with the shims, the tutorial doesn't mention that the path is actually FS0:\GUIDSystem\Library\CoreServices\ and fix it from the EFI cli as vim is not intuitive for casual use.


15. Reboot several more times to verify it's actually working reliably

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