High Sierra

14 Aug 2018

macOS version 10.13.0, called "High Sierra," was released on 2017-09-25. It is a free update to 10.12 Sierra. This note describes how to update a computer from an older version of macOS to OS X 10.13 High Sierra.

Apple released MacOS 10.13 Supplemental Update on 05 Oct 2017, fixing a security bug.
Apple released MacOS 10.13.1 on 31 Oct 2017, fixing security bugs including the KRACK vulnerability.
Apple released Security Update 2017-001 v10.13 on 29 Nov 2017, fixing the "root login" bug.
Apple released Security Update 2017-001 v10.13.1 on 29 Nov 2017, fixing the "root login" bug. That fix broke file sharing between Macs; Apple has documented a fix to the fix, and re-released Security Update 2017-001 v10.13.1 with the fix.
Apple released MacOS 10.13.2 on 06 Dec 2017, fixing the "root login" bug again, as well as other security problems.
Apple released macOS High Sierra 10.13.2 Supplemental Update on 08 Jan 2018, to mitigate the effects of the "Spectre" bug.
Apple released MacOS 10.13.3 on 23 Jan 2018, fixing a few bugs.
Apple released macOS High Sierra 10.13.3 Supplemental Update on 20 Feb 2018 fixing the Telugu crasher bug.
Apple released macOS High Sierra 10.13.4 on 29 Mar 2018, fixing a few bugs. Problems with multi-monitor configurations have been reported.
Apple released macOS Security Update 2018-001 on 24 Apr 2018, fixing three security bugs.
Apple released macOS High Sierra 10.13.5 on 01 Jun 2018, fixing a few bugs.
Apple released >macOS High Sierra 10.13.6 on 09 Jul 2018, fixing security bugs and updating device firmware.

I have installed High Sierra on one computer. I am waiting to resolve my problems with Quicken before I install it on my personal machine.

High Sierra ships with new Macs. The latest version of Mac OS X is version 10.13, "High Sierra", released in September 2017.

New Features of High Sierra

There is a new file system, called APFS. Installing High Sierra will reformat your storage if your machine has an SSD. This new file system has caused problems with some applications.

New graphic and video formats are supported, which will make smaller files.

Mail, Photos, Siri, and Safari have new interface features.

Should I Install High Sierra?

Show Stoppers

Check MacInTouch for the latest status.

Installation Problems

Some users whose disk is encrypted with FileVault report that their attempt to install will not accept their unlock password. (Thanks to Marv Schaefer for this tip.)
Another friend attempted to install High Sierra and ended up in a panic/reboot loop. It took many hours of Internet recovery to complete installation.

Users who have Fusion drives are having problems installing the system. APFS support is apparently incomplete.

A MacInTouch reader reported problems upgrading; when they finally got High Sierra installed, all their mail messages were missing, and application license data was lost.

Some users report that their attempt to install fails with the message "macOS could not be installed on your computer" halfway through. Make sure you clone your hard disk before you start installing. Some users had trouble installing the Supplemental Update.

Migration Problems

I bought a new computer for a family member. The machine came with High Sierra. I used Migration Assistant to move files and settings from the old computer that was running El Capitan. Multiple problems ensued.

Apple software

Users reported that Mail.app randomly loses settings. A few users reported persistent Finder freezes.

Third party apps

Quicken 2007 will not make backup files on an APFS volume.

Illustrator and Photoshop have problems reported on High Sierra. If you have Creative Cloud, update to the latest CC versions and check for updated plugins. I migrated my CS5 versions to High Sierra, and they sort of work: can't use Suitcase with them any more, and some Illustrator features I never use are known to cause immediate crashes.

Some 32-bit applications will work under 10.13 but this is the last macOS to support them "without problems."

Installed MS Office 2016. Many things are different.

What you Should Do Now to Get Ready for High Sierra

Who Can Update

Not everyone can use the new OS version.

Plan your install

When you decide to install High Sierra, do it carefully. You may find that there are issues that affect you: do your homework. Check MacInTouch to see if there are problems with macOS 10.13 that affect you.

Make sure you back up your entire disk before starting to install High Sierra. Preferably to more than one place.

Make a list of the hardware you depend on, and search the web to check that each device will work. Older printers and scanners can have issues.

Leave yourself enough time. Upgrading will tie up your computer for a big part of a day. Installing takes an hour or two, but then your computer will be very slow until it re-does the Spotlight index and does a big backup up to Time Machine.

Particular issues before upgrading

Here is a partial list of minimum program versions needed for High Sierra. For other programs, check product websites, or RoaringApps.

ProgramMinimum VersionNotes
Microsoft Office2016See below.
VirtualBox5.1.26free
Quicken2018$35/yr. See below.
Adobe AcrobatXI Pro Support ended in 2017. Supposedly still works. See below.
Adobe PhotoshopCC Known problems. See below.
Adobe IllustratorCC Known problems. See below.
Suitcase Fusion 718.2.4Photoshop and Illustrator issues. $60 upgrade to Fusion 8.
Little Snitch3.8.2
MacPorts2.4.2free
Apple XCode9free with registration
DropBox39.4.49free
Super Duper3.1.1$27.95
Apple OS X Server5.4

Currently, Adobe says that Illustrator and Photoshop CC do not work on High Sierra and they will fix them in a future version.

Adobe no longer sells regular application versions of Photoshop and Illustrator. Instead they rent you a Creative Cloud subscription. Stop paying, the apps stop working. They tell you that one advantage is that you'll get bug fixes and new features whenever they decide to release them. (There are a lot of tricky deals, initial teasers, different bundles. You could pay $20/app/mo or $600/yr for all CC apps. Adobe also sells Photoshop Elements as a non-cloud application for $70 one-time.)

Similar deal for Adobe Acrobat.. Acrobat Pro DC rents for $179/yr for the rest of your life, for 2 users. (Acrobat XI Pro may still work on High Sierra.) You might be able to buy a lifetime copy for $449, but websites don't say how many computers are covered. If you search the web for replacement products, there are some listed. PC World suggests Nitro Pro 11, $160 lifetime for up to 10 users.

There are alternatives to Adobe products, such as much less expensive Affinity Photo and Affinity Designer. There are also free programs such as Polarr Photo Editor and GIMP. With any of these replacements, you have to learn how to use new programs, and worry about compatibility.

Microsoft wants to rent you "Office 365." (Again there are multiple deals: for about $70/yr/computer you can get the whole suite. You can also buy non-cloud Office 2016 Home & Student for $150 one-time. This is what I did.)

Quicken 2007 (Lion update) sort of works on High Sierra; won't make a backup to an APFS volume. Since this is 32-bit software, it won't run on the macOS scheduled for 2019. Quicken wants to rent you Quicken 2018 for Mac for $35/yr. This is a show stopper for me.

Installing High Sierra

I updated a 2012 Mac Mini to High Sierra. Since the Mini does not have an SSD, the update did not install APFS. This install took about 3 hours.. it would have taken additional time to change the file system. Then I had to install Hig Sierra 10.13.4 and update various Apple software: this took 3 more hours.

  1. Clean up and update software before installing.
    • (If your Mac is running a very old version of OS X, you must install Snow Leopard 10.6.8 first, in order to get a version of Apple App Store that can download High Sierra. Here is Apple's how to upgrade page.)
    • Download High Sierra from  ► App Store...  ►  Updates. It is free. This downloads a large file, the High Sierra Installer, to your disk. You can create a bootable installer volume on a USB key using these instructions. (But see the TidBits article "Previously Downloaded OS X Installers No Longer Work".) Apple's license terms say you can update all your computers with one purchase.
    • Get the applications on your computer ready for 10.13: apply the latest fixes.
    • Delete junk files. Carefully.
    • Delete Safari, iTunes, and Firefox caches, so your backup will be faster.
    • If you have customized your desktop background or screensaver, write down your settings. Some Apple-provided pictures may not be available in the next version.. make a safe copy of anything you will want after upgrading.
    • Empty the Trash.
    • Clean up damaged and duplicate fonts.
    • If you use Apache, save a copy of /etc/apache2/httpd.conf.
    • If you installed modules via CPAN, Macports, or Fink, make a list of them. In a Terminal window, type
      perldoc perllocal | grep :: > cpan_modules.txt
      port -qv installed > macports_packages.txt
    • Have your software license keys handy in case you have to re-authorize products.
    • De-authorize Adobe Photoshop and Illustrator.
    • De-authorize your computer from iTunes.
  2. Backup and prepare.
    • If you use MySQL, backup the database with mysqldump databasename > db.sql
    • BACK UP YOUR HARD DRIVE to an external disk. I used SuperDuper to clone my whole drive. Some cautious people make two backups.
    • If you installed a third-party Solid State Disk (SSD), check the manufacturer's website to see if you need to update its firmware to work with High Sierra.
    • If you connect your Mac to the network using WiFi, select  ► System Preferences... ► Network ► Advanced and delete any WiFi networks you don't want to use. (I forgot to do this, and my computer connected to a very slow network, which slowed down my install.)
    • The best way to handle Macports is to uninstall all the old ports and reinstall after updating the OS. In a Terminal window, type
      sudo port -fp uninstall installed
  3. Install
    • If you use a wireless mouse or keyboard, put in fresh batteries.
    • Set screen saver to NEVER, and turn off Time Machine.
    • Dismount and unplug or power off external drives.
    • Run the macOS 10.13 installer. If FileVault is enabled on your computer, the installer will ask for a password to unlock the disk. It will run for about 15 minutes, then reboot, then run for about an hour, then reboot again. (The "time remaining" will show wildly varying estimates as the installer proceeds. Don't panic if you see a gray screen with "30 minutes remaining" for an hour. Just let it run.)
    • As the update finishes, it will ask you for your AppleID password.
    • If High Sierra asks you if you want to enable Desktop and Documents folder syncing to iCloud, the safest thing to do is to say NO. If you say YES, these folders will be backed up in iCloud and available on all devices, which you may not want, and saying YES may also enable "Optimize Storage" which will delete files from your computer's drive if it gets too full. Adam Engst's TidBITS article on Optimized Storage is very helpful.
    • Select  ► App Store... to update to latest versions of Apple software, then run it again to make sure all software is updated. (about another hour) If you just downloaded the OSX installer from the Apple Store, you will have the latest version of OSX, but this step may find additional application updates.
    • Do a "smoke test" to verify that your computer is working OK. Make sure the applications you depend on are still working. Try out the applications from Apple that were updated with the OS. If you have trouble, restore your backup and go back to the old OS version.
  4. Recover
    • When you attempt to re-authorize Adobe Photoshop and Illustrator, or the first time you execute them, you may see an alert box that tells you that you have to install Java 6 first (even if you have Java 8 installed). Click "more Info" and download and install the update. See above for a gotcha regarding the "quarantine" switch.
    • Re-authorize your computer in iTunes.
    • Wait for Spotlight to finish indexing (may take several hours). Performance will suck till it finishes.
    • Turn on Time Machine and start your backup.
    • You don't have to repair disk permissions with Disk Utility any more. In fact, you can't; the option is gone.
    • Restart the computer. Often this speeds things up.

Post Install Tasks

Once you are satisfied that your computer works acceptably, and you are going to stay on High Sierra, you can make some adjustments.

Customization

You will probably want to set up per-user customizations, such as your desktop background and screensaver. After each new OS generation this is something of an adventure; functions get renamed and moved around.

Security issues

Under Sierra, Spotlight "shows suggestions from the Internet, iTunes, App Store, movie showtimes, locations nearby, and more." To do this, it sends your location and query to Apple servers. You may wish to change this if you are required to keep some information private. Change it in two places: uncheck "allow Spotlight Suggestions" in  ► System Preferences... ► Spotlight ► Search Results and uncheck "Safari & Spotlight Suggestions" in  ► System Preferences... ► Security&Privacy ► Privacy ► Location Services ► Privacy ► System Services ► Details.

Some kinds of security certificates are no longer accepted. These are the ones using SHA-1, which is deprecated.

Devices

Programming Tools

  1. In Terminal, type the command java. If you don't have Java 8 installed, this action will bring up a dialog box: click More Info to bring up the Oracle JDK installation page in a web browser, and trigger the installation of the Java 8 JDK from Oracle over the Internet. Java is needed for Eclipse and for other Mac applications, such as OpenOffice and some Adobe products, and VPN clients such as Cisco. Java is not dangerous, if you use it to run code you trust: using it to run web page animations has had some problems.
  2. If you use your computer for programming, install the (free) Xcode Developer Tools by typing xcode-select --install in a terminal window, or by installing the whole Xcode package using the App Store. Then type sudo xcodebuild -license in a terminal window to accept the license.
  3. MacPorts: see my instructions for MacPorts page. Basically the procedure is to list your ports and uninstall them before upgrade, install the OS, reinstall MacPorts, and reinstall your ports. Set PERL5LIB=/Users/myname/bin:/opt/local/lib/perl5/site_perl/5.26 or installs will fail with messages about variants. You will need to disable SIP to complete these installs.
  4. MySQL: Version 8.0.1 appears to work on Sierra and High Sierra.
  5. Perl/CPAN: Perl 5.26.2 is installed by MacPorts. See my instructions for CPAN.
  6. Apache web server:
    • Apache 2.4.28 is provided with High Sierra, but is not automatically started and there is no System Preferences interface to enable it.
    • The new OS install will not carry over your old Apache customizations. diff /etc/apache2/httpd.conf against your saved copy and edit as necessary.
    • Start Apache using the terminal command sudo launchctl load -w /System/Library/LaunchDaemons/org.apache.httpd.plist. The -w means make it permanent across restarts.
    • PHP 5.6.30 is shipped with the OS but disabled in httpd.conf, same version as for Sierra. I sometimes enable PHP in order to debug programs that will be deployed in safe environments on other computers. If you enable it, be aware of the risks of making PHP available on the Internet from your Mac, and track and install security updates.
  7. Screen saver: if you patched the duration of a screen saver slide, as I did, you will have to reapply the patch.
  8. Login screen: if you replaced the login screen background, as I did, you will have to reapply the patch.

After all installations are done, re-enable SIP by booting into the recovery environment and typing csrutil enable .

High Sierra Observations

New Features and Changes

Many of the advertised features of High Sierra sound uninteresting or worse to me.

AFS file sharing will not work from an APFS drive. In  ► System Preferences... ► Sharing, click on "File Sharing" and "Options", and check "Share files and folders using SMB." This will cause trouble if you are trying to share files with an old Mac.

Unsigned kernel extensions will not load.

Apparently there is a hidden way to repair permissions. Apple Support Note HT203538 suggests the Terminal command diskutil resetUserPermissions / `id -u`.

The Photos app has been upgraded to 3.0. It adds better picture editing, and rearranges the controls and menus again. The "Faces" feature of Photos works even worse than in Sierra: mystery meat navigation, no way to find Unnamed faces, no way to delete non-faces or don't care strangers.

Unchanged

Third party apps that appear to work OK:

Bugs/Gotchas in High Sierra

Removed Features

Planning for the next version

Keep a list of the software and devices you use and depend on, so you can check that they are supported.

32-bit programs

The next macOS version will probably release in Fall 2018. Apple has announced that this version of macOS will not support 32-bit software "without compromise." The next version won't do 32-bit at all. Start planning. To list the 32-bit programs on your system, you can execute this line in Terminal:

  system_profiler SPApplicationsDataType | sed -e 's/ *//' | grep -A4 "64-Bit (Intel): No" | grep Location

Home | FAQ © 2010-2018, Tom Van Vleck updated 2018-08-14 13:56