(I was going to make a thread about this, but Stefan beat me to it. Here's what I was going to write:)
So I've tried and failed four times to install the macOS High Sierra 10.13.3 Supplemental Update on my iMac Pro. And much more annoyingly, after each attempt, I've had to reinstall the whole operating system. I had no problem installing the update on my MacBook Pro.
First I downloaded the update through the App Store like usual and clicked "Restart" when instructed to... Only to be met with a screen that says "The version of macOS on the selected disk needs to be reinstalled". (That error message BTW returns no search results on Google, which I find very weird and worrying.) At that point, I wasn't sure if it was the update that was the culprit, or some apps that I had just installed before the restart. But now, after three more attempts, I'm sure it's the update.
I was very worried that I would lose all my files if I just went through with the reinstall. After some googling, I managed to copy my files to an external hard drive through Recovery Mode. After that I proceeded with the reinstall.
Okay, so now I had reinstalled High Sierra for the first time. I checked the App Store for updates, and it offered me the Supplemental Update again. I downloaded it, clicked "Restart", and was again met with the message that I needed to reinstall the operating system. I went through with the reinstall again.
After the second reinstall, and after some googling, I tried to download the update through Apple's website (https://support.apple.com/kb/DL1957?locale=en_US) rather than through the App Store. But the same thing happened, I had to reinstall the whole operating system, now for the third time.
So after this, I contacted Apple's support chat, and explained the problem. They advised me to try downloading and installing an older update through their website (https://support.apple.com/kb/DL1952?locale=en_US). The installation went smoothly. Afterwards, the App Store again offered me the Supplemental Update. I tried to install it, thinking that the DL1952 update had fixed the problem. But again, for the fourth time, I was met with the error message that I had to reinstall the operating system.
This has wasted like two days of my time, googling for help, backing up my files to an external drive, waiting for the very slow reinstalls to complete, chatting with support... _Extremely_ annoying.
I've now hidden the Supplemental Update from the Updates tab in the App Store, and I'm obviously not going to try installing it again. There's clearly something wrong with it.
I suspect this is specific to the iMac Pro. As I said, I had no problem installing the update on my MacBook Pro. And interestingly there are separate update files for the iMac Pro and all other Macs:
https://support.apple.com/kb/DL1957?locale=en_US
https://support.apple.com/kb/DL1958?locale=en_US
Some things that might be important:
- I have FileVault full disk encryption on
- I have set a firmware password
- I'm dual booting Windows 10