Updating to macOS High SierraEdit

Created , updated

NOTE: I ended up having to downgrade to Sierra due to getting locked out by Active Directory issues, which suprisingly ended up with me losing the ability to unlock the encrypted volume. Good thing for backups.

Foolishly decided to upgrade more or less immediately when High Sierra came out, even though I usually prefer to wait for a couple of point releases (sometimes more when waiting for updates to critical third-party software). The allure of being rid of HFS+ once and for all was just too great.

Fair number of horror stories on Twitter about stuck installs etc but I fortunately didn’t hit any of those snags. Instead, I had a few others.

Can’t log in after installing

Fruit of the fact that I have a corp-managed laptop with a network account. People have reported difficulty unlocking the encrypted disk and then logging in even when unlocked. I basically assumed both issues might be at play so ran through the suggested fixes for both:

  1. Reboot in recovery mode (Command-R), which required me to do a hard reset (because I couldn’t even restart without the system accepting my password); this explains some issues with orphaned socket files that I later ran into (see below).
  2. In the Terminal: diskutil apfs list (to find the disk name, eg. disk2s1).
  3. diskutil apfs unlockvolume disk2s1 (to mount).
  4. diskutil apfs updatePreboot disk2s1 (this should solve any issues unlocking the disk).
  5. rm /Volumes/$VOL/var/db/.AppleSetupDone (this to allow me to create a local, non-network account).
  6. reboot
  7. Log in to local account.
  8. sudo passwd $OTHER_USER
  9. Reboot.
  10. sudo chefctl -i (machine is managed by Chef).
  11. Remove local account.

New shells open with $HOME set to /var/empty

This one happened a couple of days in a row, a few days after upgrading. More Active Directory weirdness, I presume.

sudo dscl localhost read /Local/Default/Users/$USER CopyTimestamp
sudo dscl localhost delete /Local/Default/Users/$USER CopyTimestamp

Other issues

  • Karabiner-Elements needs to be explicitly enabled in the Security pane of the System Preferences.
  • xcode-select --install didn’t work for me, claiming the command-line tools were not available to download; nevertheless, I have Xcode 9 on the system.

vim, nvim are broken

Here I thrashed around trying to reinstall.

brew update
brew upgrade
brew uninstall neovim
brew install neovim         # Nope, still crashing
brew uninstall neovim
brew install --HEAD neovim  # Still crashing, Vim too.
sudo gem install neovim     # Works.
brew uninstall vim
brew install --HEAD vim     # Still crashing, but will just use nvim.

After this, rebuild Command-T (ie. make clean && ruby extconf.rb && make). Didn’t need to reinstall everything (ie. brew list | xargs brew reinstall) but might be worth a thought at some point.

Other steps

  • Turn on iCloud recovery key again (apparently, Apple got rid of this when they rolled out Two-Factor auth a while back because it was too easy for people to totally lock themselves out, but looks like it is back).
  • brew doctor, just in case.

Clipper is broken

Random attempt at uninstalling/reinstalling didn’t work, then I realized a stale socket file was lying around preventing it from starting:

brew uninstall --force clipper  # --force because I have multiple versions.
brew install clipper
brew services start clipper     # Claims it is already running.
brew services restart clipper   # Nope, still not working.
rm ~/.clipper.sock              # Found the culprit.
brew services restart clipper   # Works.

Mutt set-up is broken

Mutt works, but imapfilter can’t log in. Turns out that it just can’t get the password info out of Passage. Same fix as for Clipper:

rm ~/.passage.sock

Note I didn’t even need to restart it, launchd did it for me automatically.

Sending mail

This was broken due to missing gems. I tried installing them:

sudo gem install mime-types-data mime-types mail

But they didn’t match the lockfile and I hadn’t bothered to pin explicit versions, so I tried to blow away the lockfile and install again, but Bundler was broken too and I couldn’t install it:

sudo gem install bundler # no implicit conversion of nil into String
sudo gem update --system
sudo gem install bundler # You don't have write permissions for the /usr/bin directory.
gem install bundler # You don't have write permissions for the /Library/Ruby/Gems/2.3.0 directory.

gem environment and sudo gem environment show the same thing:

INSTALLATION DIRECTORY: /Library/Ruby/Gems/2.3.0
EXECUTABLE DIRECTORY: /usr/bin

Solution was to add gem: --bindir /usr/local/bin to the ~/.gemrc, then sudo gem install bundler worked, and bundle did too.

Searching mail

Broken because the ~/.mutt/tmp/notmuch.history history file format needed to be updated as per this Stack Overflow answer:

  • Insert header of _HiStOrY_V2_.
  • Replaces spaces with \040 (ie. :%s/\v /\\040/g in Vim).