Show notes
So, in today’s show, you’ll learn how to safely perform a major OS update on your iPhone, iPad or Mac.
For that, I’ve laid out a step-by-step process that will help you minimise the risk of losing data and precious time.
At the time of recording, the iPhone and the iPad are now on iOS 13.1.2 and macOS 10.15 Catalina just got released for the Mac.
If you’re not sure whether or not you should update your Apple gear to the latest and greatest version of the operating system, I invite you to pause this episode right now and listen to episode 45.
Spoiler alert, if your iPhone or iPad is compatible, at one point you’ll need to pull the trigger while on the Mac side, you don’t necessarily need to update it, and even if you do, you’re not obliged to install the latest and greatest.
Talking specifically about macOS Catalina, because it is bringing so much architectural changes and breaking compatibility with older apps, it’s more important than ever to proceed with caution, whether you’re listening to this episode in 2019, 2020 or even 2021.
Now, whether you need to upgrade or decided to upgrade, this episode will guide you step-by-step on how to perform it.
iOS/iPad OS update process
First, I’ll talk about the iPhone and iPad, and then I’ll cover the Mac.
Okay, so let’s start with the iPhone and the iPad
- Make at least 1 backup, preferably 2
- Gather the PIN code of your SIM card and important passwords
- Decide the upgrade method
- Start the upgrade
- Setup your device
- Optional: Upgrade your Apple Watch
Step n°1 is to make a least 1 backup and you have two options: either through iCloud or via a computer.
iCloud storage is very affordable: for $3 per month you can get 200GB, which is enough if you have a 128GB device and a medium-sized photo library.
If you have a device with more capacity and it’s full, then you can bump your iCloud storage capacity to 2TB for 1 month or two. It will cost you 10 to 20 bucks total, then when you don’t need the backup anymore, you can delete it from iCloud and downgrade your storage back to 200GB or 50GB.
The second option, and yes, I recommend to do both, is to perform a locally encrypted backup to a computer, can be a Mac or a Windows PC with enough free storage to accommodate the content of your iOS device.
On a Windows PC or Mac running Mojave and earlier, it will be done via iTunes, whereas if your Mac is running at least 10.15 Catalina, it will be done via the Finder.
In any case, you’ll need to connect the device to the computer via a USB cable, and if it’s the first time, you’ll need to manually trust it by tapping on Trust then entering your device passcode.
In iTunes, you’ll need to click on the device icon in the top left corner and in Finder, you’ll need to click on the device name in the Sidebar on the left.
Then, make sure that the option to encrypt the local backup is ticked and if not, tick it, then enter a password that you’ll need to remember or store in a password manager to access and restore the backup later on.
Wait for the backup to complete and depending on the amount of data on your iOS device, it can take a while.
Now, it’s not finished yet. What we want to do next is to archive the backup so that it cannot be overwritten.
For that, click on « Manage backups » in Finder or access iTunes preferences pane using the CTRL Comma shortcut, then click on the « Devices » tab. Now right-click on the last backup performed for that device, then choose the option « Archive »
OK, we have at least 1 backup, preferably 2
Step n°2 for an iPhone or an iPad with cellular is to gather the PIN code of the SIM card, because to make the upgrade, the device needs to reboot and thus we’ll need to be able to supply the PIN code upon restart.
Now is also a good time to retrieve the PUK code because if you ever forget your PIN code, the PUK will give you the option to set a new PIN without needing to visit your cellular plan provider.
Credentials gathering continues with the iCloud password and the password of important e-mail and web services, as you never know if you’ll need to re-authenticate yourself after the upgrade.
If you don’t use a third-party password manager, the first place to look is in Settings > Passwords & Accounts > Website & App Passwords
Step n°3 is to decide which upgrade method to take. You basically have 2 options, either you do it over-the-air by downloading it directly onto your iOS device or you do it plugged into a computer, using iTunes or Finder.
In the past, before app offloading was a thing, one needed to use a computer when there was not enough free storage on our iOS device to even download the update.
Nowadays, it’s less problematic, unless your device has only 16GB of internal storage.
An advantage of doing it over-the-air is that it requires to download a smaller package than via a computer. It’s about 2.2 GB over-the-air and 3.8GB via a computer.
So, if you have a low monthly bandwidth cap with your ISP and provided that you have enough available internal space, do it over-the air, otherwise use a computer.
Same thing as with the backup, you’ll use iTunes if you have Windows PC or a Mac running Mojave and earlier and you’ll use Finder with Catalina and later.
Step n°4 si to start the upgrade which will take between half an hour and an hour, so it’s best to do that in the evening or during the week-end.
Step n°5 is to finish the update by entering the PIN code of your SIM card then setting up various parameters, like dark mode.
When you’ll launch certain apps for the first time, you’ll see what’s new and improved and in some cases, you’ll be asked whether or not you want to upgrade the database.
With iOS 13, it’s the Reminders database that will prompt you and it’s very important to understand that if you upgrade it, you can’t go back.
Basically, if you want to continue synchronising your Reminders with devices stuck at iOS 12 and macOS Mojave or earlier, you should say NO to the upgrade.
Apple will show you a list of devices that have not been upgraded yet and if you see mission-critical ones, DO NOT upgrade the Reminders database.
On top of that, some people reported that after upgrading the database, all their reminders disappeared and only reappeared half a day to a day later.
Again, if you decide to upgrade the Reminders database, do so when you know you don’t absolutely need it and keep in mind that your Reminders won’t sync with devices running older versions of the operating system.
This applies in a Family Sharing environment too, meaning that you may lose synchronisation of a shared list if only some devices get their database upgraded.
Step n°6 is optional and is for Apple Watch Series 1 and above owners.
Once your iPhone is running iOS 13, you’ll be able to update your Apple Watch to watchOS 6.
Here it’s the standard process:
- Put your Apple Watch on its charger and wait until it’s 50% charged
- Connect your iPhone to Wi-Fi
- Put your iPhone in close proximity to your Apple Watch
- Open the Apple Watch app on your iPhone
- Tap the “My Watch” tab
- Tap on General > Software Update
I’ve compiled all this process in a neat PDF here: iOS 13 Upgrade checklist
macOS update process
Ok, now let’s talk about safely updating your Mac.
As explained in episode 45, my recommendation is to stay at least one version behind the latest one for all the mission-critical machines.
The main reason is that Apple provides security updates for the last 3 versions of macOS, so there’s absolutely no rush to upgrade to the latest and greatest.
It’s not like for the iPhone and the iPad where a compatible device absolutely needs to be updated to get security updates.
Another advantage of upgrading to an earlier version of macOS is that you’ll skip all the intermediate minor updates and go directly to the most stable version of that operating system.
For example, let’s say that your computer is running macOS High Sierra and is compatible with both Mojave and Catalina.
At the time of recording, Catalina just got released, so if you upgrade right away to the 10.15 version, you’ll need to also go through the 10.15.1 update, the 10.15.2 update and so on until Fall next year.
On the other hand, if you upgrade to Mojave, you’ll go right away to 10.14.6 and you’ll only need to install the latest security updates until you upgrade again.
So, here are the 7 steps for the macOS update process
- Decide which version of macOS you’ll upgrade your computer to
- Make screenshots of all your System Preferences panes
- Perform at least 1 backup, preferably 2
- Gather your most important passwords
- Download the desired macOS Installer
- Initiate the update
- Finalise the update
Step n°1 is to decide on the version of macOS to upgrade to.
For that, you’ll evaluate the compatibility of the software and peripherals you rely upon for your business.
- Make a list of the potential version of macOS you could upgrade your computer to
- Make a list of the software and peripherals you use on a daily or weekly basis
- Software
- Visit the developer’s Web site or the crowdsourcing site RoaringApps and check the latest version of macOS that is compatible
- For Catalina and later, download and run the Go64 utility which will list the 32-bit apps and libraries that are not supported anymore
- Peripherals: Visit the manufacturer’s page and look for drivers for the exact model number
- Check which macOS version is compatible with all your apps and devices.
If there’s a macOS version that is 100% compatible, great, you’ve found the one.
If none are 100% compatible, then you’ll need to look for alternative apps and/or hardware, and make a list of their respective cost.
If your Mac is currently running a version of macOS that will still get security updates for another year, you could decide not to upgrade right away, which will you give more time to research alternatives or for third-party app developers to make their app compatible.
Talking specifically about macOS Catalina, Adobe Photoshop and Lightroom are not compatible at launch.
It’s the same for DJ apps that rely on XML export of playlists created by iTunes, since iTunes is gone and the feature has not yet been ported to the new Music app.
Step n°2 is to make screenshots of all your System Preferences panes.
By doing that, you’ll keep a record of how your Mac and user account was setup and, if there’s a small glitch during the update process, you’ll probably be able to correct the issue by re-configuring System Preferences properly based on the screenshots.
This is a quite tedious process to go through all the preferences panes and you may never need it, but if you do, you’ll be glad you have it.
Step n°3 is to make at least 1 backup, preferably 2
The most obvious one is via Time Machine and if you haven’t configured it yet, now is the perfect time to do so.
Buy an external hard drive with at least twice the storage capacity of your Mac’s internal hard drive, plug it in then macOS will ask you if you want to use it for Time Machine backups.
First, tick the option to encrypt the backup, then provide a password twice and the first backup will start automatically 3 minutes after that.
Now, in addition to that, I recommend to also create a bootable clone of your computer. For that, I recommend to buy and external SSD drive over USB or Thunderbolt with at least the same capacity of the internal hard drive of your Mac.
Then, with a free utility called SuperDuper!, you’ll be able to create a bootable clone. There’s a paid version if you want to use it to schedule backups but for what we need it here, the free version will do.
The purpose of a bootable clone is to be able to start the computer from our old setup in case there’s a major issue after the update and we absolutely need to be able to work.
This is why I recommend a SSD, so that it will be fast enough to run macOS.
You’ll be able to choose the external hard drive by pressing the ALT key when booting the computer.
But warning, if your computer is equipped with a T2 security chip, you’ll need first to make sure that it is configured to allow booting from an external media.
For that, you’ll need first to boot into the recovery partition by pressing CMD R after rebooting the computer, then launch Startup Security Utility form the Utilities menu and tick the appropriate box.
Step n°4 is, like for iOS, to gather all your most important passwords
If you don’t use a password manager, the first place to look is the Passwords tab of the Safari preference pane.
A second place to look is the Keychain Access app accessible inside the Utilities folder inside the Applications folder.
Step n°5 is to download the desired macOS installer
To upgrade to the latest and greatest version of macOS, it super easy:
- on Mojave and later, you open system Preferences and click on Software Update
- on High Sierra and earlier, you visit the Mac App Store and it’ll be available there
But if you want to upgrade your computer to a version before, you’ll need a direct link available from the Apple Support site.
- Mojave: https://support.apple.com/macos/mojave
- High Sierra: https://support.apple.com/en-us/HT208969
In the support article, you’ll click on the direct link that will initiate the download of the desired macOS Installer.
At that point, you may need to make some space because the installation process needs some storage space.
Mojave for instance requires about 20GB of free space when upgrading from Yosemite or earlier.
Options to make space:
- Open Photos, access its iCloud Preference pane (⌘ ,) then activate « Optimise Mac Storage » if not done yet
- Open System Preferences and access the iCloud panel, click on « Options » next to iCloud Drive and activate « Optimise Mac Storage »
- Download and run a free utility called OmniDiskSweeper to find what takes the most space on your computer
Step n°6 is to initiate the update
Now, when the installer has finished downloading, it will launch immediately.
At this point, you have two choices:
- Either proceed with the installation right away
- Or create a bootable installer and then finish the installation process
If it’s the only Mac that you need to upgrade, you can actually proceed with the installation.
But if you’ve got more than 1 Mac to update and also a limited monthly bandwidth cap from your Internet Service Provider, then, I’d recommend to create a bootable installer on an USB flash drive or external disk with at least 12 GB of available storage.
So, if you’ve got an old 16GB USB key lying around and without any mission critical data on it, it’s a good candidate here.
To be used as a bootable installer, it needs to be formatted in HFS+, also known as macOS Extended, which you can do using Disk Utility.
Then, using the Terminal app, you’ll copy/paste a specific command valid for each version of the macOS installer.
Here are the links with the procedure to format the USB key and to create the bootable installer:
- How to erase a USB key and format it as Mac OS Extended (HFS+)
- How to create a bootable installer for macOS
Please be aware that this process will completely erase the USB key, so backup all the files that you want to keep before running the Terminal command.
Once you’ve created the installer key, you’ll be able to use it to upgrade your other computers without the need to download multiple times the installer from the Internet.
On the first computer, you’ll just continue where you left it off.
The installer will update some files first and when it’s done, it will reboot and complete the installation process, which itself might require multiple reboots until you’ll see the initial setup steps.
With the original version of macOS Catalina so 10.15.0 if you wish, the process stalled at various points for some users and those had to force a restart of the computer to get it complete the installation of Catalina.
In the worst case scenario, the computer is unable to boot from the internal disk and this is where the bootable clone and the Time Machine backup will come in handy.
In step 7, you’ll need to finalise the update.
This starts with going through the initial setup of the installed version of macOS by configuring various options like Siri, Dark Mode and other new features that Apple may have brought.
Then, you’ll also need to launch all the built-in apps, like Mail, Photos, Notes, Reminders and the like to see whether or not the database needs to be upgraded.
This process can take quite some time, especially if macOS has multiple gigabytes of e-mail, photos and videos to convert.
It’s not finished yet since you’ll also need to launch all your third-party apps, like Dropbox, Google Drive, Microsoft Office and so on, to re-authenticate yourself for instance, or to approve any new restrictions that Apple may have put in place.
Talking specifically about macOS Catalina, you’ll need to explicitly give all the apps permission to display notifications, to access the Downloads or the Documents folder, to access the camera, the microphone, your contacts, calendars and so on.
Yes, Apple has strengthened the security of macOS Catalina, but at the expenses of a multitude of authorisation panels that appears the very first time an app is launched.
This means that if you have a lot of apps on your computer, the first few days with Catalina will be a bit rough.
And if you’re listening to this episode right on the heels of the release of macOS Catalina, please know that some people have lost a bunch of e-mails because of a bug in the Mail database upgrade process.
And the problem here is that the deletion propagated to the mail server and onto other devices.
This is another example of why it’s unwise to upgrade to the latest and greatest version of macOS right away.
Hopefully this bug will be fixed by Apple soon so that upgrading to Catalina will be less risky.
Talking more generally now, you should realise that safely updating macOS on a Mac is more elaborate than what one might think and it also takes more time when you do it properly.
Like with the iPhone and the iPad, Macpreneurs should allocate a week-end to update their Mac in order to minimize the impact of potential issues on their day-to-day operations.