Upgrading a Proxmox 5 macOS Sierra guest to High Sierra

macOS 10.13 High Sierra has finally been released, and the good news is that it works with Proxmox 5!

Here’s how I upgraded my Proxmox 5 Sierra installation, which has been previously updated to¬†use Clover/UEFI boot and is stored on a passthrough NVMe SSD. Your setup may differ and your upgrade steps may need to change. I doubt these instructions would work for enoch/chameleon boot.

Take a snapshot of Sierra

I cannot stress this enough! If your filesystem gets completely trashed by the installer, you really need to be able to roll it back to a snapshot!

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Fixing ERR_SSL_CLIENT_AUTH_SIGNATURE_FAILED on macOS

After reinstalling Mac OS Sierra, I found that Chrome could no longer use my HTTPS client certificates. Instead, after choosing my certificate from Chrome’s pop-up certificate picking menu, I just got a fatal “ERR_SSL_CLIENT_AUTH_SIGNATURE_FAILED” error. The HTTPS client certificates worked fine in Safari, so it seemed to be a Chrome-specific problem.

I was able to fix this by opening the Keychain Access program, right-clicking my HTTPS private key and selecting Get Info, then on the Access Control tab I changed it from “allow all applications to use this item” to “confirm before allowing access”. The next time I tried to view the website in Chrome, Mac OS popped up to confirm that I wanted to allow it to use the key, and it worked perfectly after clicking Allow! I guess the Keychain’s application permissions got messed up at some point, and this reset it.