Back up then step your Mac up to El Capitan

2015-09-30 by . 0 comments

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Today is the day Apple releases OS X 10.11 – El Capitan.

I’d like to help everyone to a smooth, prepared and successful upgrade.

Before looking forward, let’s look back.

  • When was the last time you performed a Time Machine backup?
  • Do you make bootable backups?
  • Have you ever used a backup to restore my system?
  • Do you have a list on paper of the apps you consider deal breakers? (i.e. If Microsoft Word and Evernote and Dropbox do not work and work well, I will erase my Mac and reinstall the older OS until those programs get updates or I can find an alternative.)
  • How much storage space does your Mac use today and how much space is available on your backup drive?

You don’t have to answer yes to any or all of these questions, but I always recommend one exercise before any upgrade. Take out a 3×5 note card and hand write two specific statements:

My last backup is XXX days old and I’m prepared to do the work to use it if something bad happens during the upgrade.

Today, I’m willing to devote X hours and Y minutes to reading, downloading, preparing and doing the upgrade work. When the install is done, I’ll have more/less time to get adjusted and learn what has changed and test my apps: Audio Hijack, OmniGraffle, Acorn, PCalc, etc…

Doing this quick exercise ensures you have set your personal expectations and can enjoy the excitement of testing new shiny software without leaping before you are ready. Hand writing it on paper slows me down in a way that verbally agreeing to a blog post’s checklists just can’t do.

Now, for the fun part – let’s look forward.

The big features that you will notice is a revamp of full screen / split screen for apps and a new system font with an old system font name. Spotlight is seriously bulked up as is the malware protection and gatekeeper restrictions to ensure apps don’t mess under the hood with the system. Apple’s apps have been rewritten for major performance upgrades in terms of speed, responsiveness and energy savings. You will need to upgrade most third party apps to take full advantage of Apple’s changes, but even running the same app can be faster if Apple’s supporting programs are more efficient and use less resources.

Apple Lists the dozens of changes and enhancements at

I want to call out one major change that will delight you or infuriate you. Apple has made numerous workflow and app layout changes (buttons, colors, controls, etc…) so if you like your Safari tabs to do exactly what they did last year, you might not appreciate the new changes. All sorts of cross-application integration has been added so you can do tasks faster than before once you’re mastered the changes. Maps, Notes, Photos, Mail, Safari all work together better and there are subtle visual clues you will probably have to learn by reading the manual or asking/watching someone who has explored the new software.

Apple has done far, far more user testing with the AppleSeed program, the public beta program and letting developers kick the tires on El Capitan since WWDC in last June. Yes, there are some major changes to System Integrity Protection that will break many programs that don’t ship from the Mac App Store. Yes, all sorts of drivers and extensions and developer tools will need some work or major work to accommodate these changes. For the vast majority of users, the upgrade will be smooth and painless as long as realistic time estimates and a plan for support are at hand. The upgrade script is designed to avoid numerous problems, nonetheless you might have a different setup and need to re-do the upgrade if things hop off the rails that Apple has laid out for us.

With all that out of the way, here are two suggestions on how to upgrade your Mac. First, open System Information with your backup drive(s) connected and write down the free space and total space numbers for all the disks on the back of your notecard where you wrote out your time expectations and deal-breaker apps.

The “All-In” Plan

Ingredients: A hard drive you can set aside until you’ve finished testing the new OS or a sense of adventure to proceed without investing time and material consisting of a backup drive and a bootable backup.

  1. Make a bootable backup (CCC/SuperDuper/DU) – see backup options below for the tools to make this backup
  2. Download the El Capitan installation app and install all App Store updates and third party updates if they are ready for El Capitan.
  3. Save a copy of the installation app to your external drive (or a USB drive)
  4. Reboot your Mac – hold option when you hear the chime and select the bootable drive. Make sure you can log in and your deal-breaker apps all run. Don’t make any changes to files, just check that your backup is operational.
  5. Power off your Mac – disconnect the backup drive once the Mac is off
  6. Power On and optionally clean out downloads, other files you don’t need cluttering up the Mac (and /usr/local if you place things there) and empty the trash.
  7. Glance at your note card to re-set your expectations
  8. Run the installer and go make a cup of tea, coffee once the progress bar starts giving time estimates (if not sooner).
  9. The Download might take an hour or more if the servers are busy, and the install itself should take less time than the full backup does, but not less than 30 minutes for the installer to run in many cases.
  10. Open the App Store and update all apps
  11. Keep the backup drive disconnected and safe until you’ve tested all your seldom used apps. Seek support (see below) if your deal-breaker apps have problems or the install fails in some manner


The “Test Drive” Plan

Ingredients: A hard drive or partition on a hard drive with enough space to hold your entire system and data

  1. Make a normal backup if you do so (consider the pictures that make you happy if you don’t currently back things up)
  2. Download the El Capitan installation app
  3. Save a copy of the installation app to a USB drive
  4. Connect the backup drive you will use for your “Test Drive” of El Capitan.  Use Disk Utility to erase the drive. (Optionally,  partition a section of the drive to be your El Capitan OS install. Select GUID partition format and Apple Extended file system if you go the partition route).
  5. Optionally clean out downloads, other files you don’t need cluttering up the Mac (and /usr/local if you place things there) and empty the trash.
  6. Run the installer but be sure to install El Capitan to the USB drive and not install the OS on the Macintosh HD.
  7. When the installer finishes, you should boot to the welcome screen instead of your usual Mac. If not, power off the Mac and hold the option key after you press the power on key. Boot from the USB drive
  8. Look for a prompt to restore files from another Mac – choose that and “restore everything” from the Macintosh HD
  9. Now you can use the option key to select if you want to boot into Yosemite (using the internal drive) or into El Capitan (using the external drive and a copy of your data).
  10. Be sure to upgrade your apps on El Capitan and be mindful of not making changes to the same document in both places. Come up with a plan to move forward with the upgrade or erase it and wait for changes if you find El Capitan not ready for your uses.
Be sure to choose the location properly when you install on to a USB drive

Be sure to choose the location properly when you install on to a USB drive

The downsides of this plan is that you spend more time shuffling between systems, but you have two systems so it takes no time at all to revert to your old Mac. I recommend the All-In plan since in most cases, it’s enough to have a bootable backup since the vast majority of people won’t have problems. If you think you have a very rigid workflow and are unwary of changing things on a first release of a new OS or have third party apps you suspect will be problematic, the “Test Drive” is well worth the extra effort.


Backup Options

I highly recommend just buying a new backup drive from Costco or your local store that stocks decent hard drives. $90 to have a new drive to do a first backup of your system before upgrading and to put your old backup drive on the shelf “just in case” is a great value.

  • Carbon Copy Cloner – 30 day free trial
  • Super Duper – free version includes free support!
  • Disk Utility – it works, but if you already knew how to use it, you probably aren’t reading this article.
  • Time Machine + Recovery HD – this works, but can take more time than making a bootable image. The benefit here is you don’t need a second drive or double the storage space by using a bootable backup just for pre-upgrade safety.

Help and advice

  • AppleCare – Direct vendor support is often the best – especially for new releases. They will know what people are experiencing before the rest of us can write up our experiences, but you might have to pay for this. Don’t go to an Apple Retail store as Apple is focusing the genius staff on hardware repairs – so your wait is almost always lower using online/phone support these days.
  • Ask Different – of course!

Filed under Apple OS X Tutorial

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