Macpreneur

How To Safely Upgrade Your Solopreneur Mac, iPhone and iPad (Rebroadcast)

• Damien Schreurs • Episode 112

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In this episode, you'll learn how to safely upgrade your macOS, iOS, or iPadOS devices step-by-step.

Show notes and video version available at: https://macpreneur.com/episode112

Highlights

  • [00:00] Introduction
  • [01:02] Preparing for macOS, iOS and iPadOS Upgrade
  • [01:53] Step-by-Step iOS and iPadOS Upgrade Guide
  • [10:53] Step-by-Step macOS Upgrade Guide
  • [26:14] Contest Announcement and Conclusion

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How To Safely Upgrade Your Solopreneur Mac, iPhone and iPad (Rebroadcast)


Introduction

You've decided to install a major upgrade of macOS, iOS, or iPadOS, and you're wondering how to do that safely. 

Today's your lucky day, as this is a rebroadcast of episode 46, which originally aired on October 13th, 2019.

It's part of what I retroactively called Season 1, and I apologize in advance for the lower production quality.

Quoting Pat Flynn, one of my virtual mentors: "You've got to be cringe before they binge."

Stick around till the end as I will talk about the contest that is taking place during the month of August and you still have a few days to participate in.

For now, let's jump into the DeLorean of Back to the Future. Let's punch in October 13th, 2019, and as soon as the intro is completed, enjoy a blast from the past.


Preparing for macOS, iOS and iPadOS Upgrade

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 one hundred eleven.

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.

Now, whether you need to upgrade or you've decided to upgrade, this episode will guide you step by step on how to perform it. First, I'll talk about the iPhone and iPad, and then I'll cover the Mac.


Step-by-Step iOS and iPadOS Upgrade Guide

So let's start with the iPhone and the iPad. The process has six steps.

First, you'll make at least one backup, preferably two. 

Then, you will gather the PIN code of your SIM card and also important passwords. 

You will decide the upgrade method. 

Next, you will start the upgrade, set up your device, and then, optionally, if you have an Apple Watch, you will be able to upgrade it as well.


Backing Up Your iOS Device

So step number one is to make at least one backup. 

And here you have two options, either through iCloud or via a computer. 

Nowadays, iCloud storage is very affordable. So for $3 per month, you can get 200 gigabytes, which is enough if you have a 128-gigabyte device and I would say a medium-sized photo library.

The second option, and yes, I still recommend doing both, is to perform a locally encrypted backup to a computer.

It can be a Mac, but it can also be a Windows PC. In any case, with enough free storage to accommodate the content of your iOS device. 

Now, on a Windows PC or a Mac running Mojave and earlier, it will be done via iTunes, whereas if your Mac is running at least 10.15 Catalina, then 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 very first time you do that, you will need to manually trust it by tapping on Trust, then entering your device passcode.

In iTunes, you will need to click on the device icon in the top left corner, and in Finder, you will need to click on the device name in the sidebar on the left.

Then you have to make sure that the option to encrypt the local backup is ticked because then you will be able to really do a complete backup of your device.

Then you will need to provide a password twice that you will need to remember or to store in a password manager so that later on, you will need that password to restore the backup.

Okay. So now you initiate the backup. You have to wait for the backup to complete. And depending on the amount of data that you have on your iOS device, it can take a while.

Now, it's not yet finished with the backup because what we want to do next is to archive it so that it cannot be overwritten later on.

So for that, if you use Finder, you will click on a button that says Manage Backups. And if you're using iTunes for the backup, you will access its preference pane using the control comma shortcut. Then you will click on the devices tab, and then in both cases, in Finder or iTunes, you will right-click on the last backup that you just performed for that device, and then you choose the option to archive.

And then, to the right of the name of the device, you will see the date and time at which the backup was archived.

Okay, so now we have at least one backup, preferably two, so you have iCloud and the locally encrypted backup.


Gathering Credentials for Upgrade

So the next step for an iPhone or an iPad with a cellular plan is to gather the PIN code of your SIM card because, to make the upgrade, the device will need to reboot.

And so, after the reboot, you will need to supply the PIN code if you want to be able to use a SIM card.

Now is also a good time to retrieve what is called the PUK code, P-U-K, because if you ever forget your PIN code, it's the PUK code that will give you the option to set a new PIN without needing to talk to your cellular plan provider.

Credentials gathering continues with the iCloud password and the passwords of important email accounts or web services because you never know if you will need to reauthenticate yourself after the upgrade or not.

Now, if you don't use a third-party password manager, the first place to look into is Settings, then Passwords and accounts, then website and app passwords. Normally, you will find a lot of passwords there.


Choosing the Upgrade Method

Okay, step number three is to decide the method for the upgrade. And you basically have two options. Either you will do it over the air, by downloading it directly onto your iOS devices via Wi-Fi, or you do it plugged into the computer using iTunes or Finder.

In the past, before app offloading was really a thing, using a computer was really needed when there was not enough free storage on the device because you couldn't even download the update.

Nowadays, it's less problematic, so unless your device has only 16GB of internal storage.

One advantage of doing it over the air is that it requires less data to download. So, we're talking about two point two gigabytes if you do it over the air. But if you do it via a computer, because it needs to download the complete updates, it's almost four gigabytes that you need to download.

So if you have a low monthly bandwidth cap with your ISP, and also provided that you have enough available internal space on your computer, it's better to do the update of the iPhone or the iPad over the air. Otherwise, use the computer for the update.


Starting and Finalizing the iOS Upgrade

Okay, step number four is to start the upgrade, which will take between I would say half an hour and an hour depending on your device. So it's best to do that in the evening or during the weekend.

Step number five is to finish the update. So remember, the device will reboot.

The first thing to do will be to enter the PIN code of the SIM card so that you can start calling and receiving SMS and so on. Then you will need to set up various parameters like if you want Siri or if you want dark mode. Also, when you launch some apps for the very first time, you will see what is new and improved.

In some cases, you will be asked to provide credentials. In other cases, you will be asked whether or not you want to upgrade the database. So, with iOS 13, it is the Reminders database that will prompt you, and it's very, very important to understand that if you upgrade the Reminders database, you can't go back.

Okay? There is no way to downgrade the database. And how to decide? 

Basically, if you want to continue synchronizing your Reminders with devices that are stuck at iOS 12 or macOS Mojave, then you should say no to the upgrade. 

You will be able to use Reminders on your iOS 13 device, but you will not have all the latest and greatest features. At least you can continue synchronizing them with other devices.

Actually, Apple will show you a list of devices that have not been upgraded yet. 

So if you see there are mission-critical ones, do not upgrade the Reminders database. 

Some people reported that after upgrading the Reminders database, all their reminders disappeared, and they only reappeared half a day, sometimes a day later.

So they were really panicking because they were like, "Oh, I've lost all my reminders." But no, this was apparently part of the upgrade process, and they came back.

Also, keep in mind that this applies in a Family Sharing environment too. So family members need to have compatible devices.


Upgrading Your Apple Watch

Last step now, it's only if you have an Apple Watch.

And here's the standard process again. So, you put your Apple Watch on its charger. You wait until it's at least 50 percent charged. Then, you connect your iPhone to Wi-Fi, put it in close proximity to your Apple Watch, and open the Apple Watch app on your iPhone.

You tap the My Watch tab, then tap on General, Software Update. Then, you will be able to update your Apple Watch to watchOS 6.


Preparing for the macOS Upgrade

Okay, so now let's talk about safely updating your Mac.

My recommendation is really 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 three versions of macOS, so there's absolutely no rush to upgrade to the latest and greatest.

Another advantage of upgrading to an earlier version of macOS is that you will skip all the intermediate minor updates and go directly to the most stable version of that operating system.

So let's take an example. Let's say that your computer is running macOS High Sierra right now, and it 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, what you'll need to do is also go through all the minor updates, so the 10.15.1, the 10.15.2, the 10.15.3, until fall two thousand twenty.

On the other hand, if you upgrade to Mojave, you will go right away to version 10.14.6, which is the last one, and you will only need to install the latest security updates until you upgrade again the next time. So, it's really less painful and also less risky.


Overview of the macOS Upgrade Process

So let's go through the seven steps that I've laid out for a macOS update process.

Step number one, we'll decide which version of macOS we want to upgrade our computer to.

Second step, take screenshots of all the System Preferences panes.

Step number three, perform at least one backup. Again, preferably two.

Step number four, gather your most important passwords.

Step number five, download the desired macOS installer.

Step number six, initiate the update. And step number seven, finalize the update.


Deciding The Version of macOS to Upgrade to

So let's go back. Step number one is to decide the version of macOS that you want to upgrade to.

For that, you will evaluate the compatibility of the software and peripherals that you rely upon for your business. So, you make a list of the potential versions of macOS that you could upgrade your computer to. You then make a list of all the software and peripherals that you use on a daily or weekly basis for your business.

If we're talking about software, you will visit the developer's website, or a crowdsourcing site like Roaring Apps, and you will check the latest version of macOS that is compatible with the apps that you use all the time.

Regarding the peripherals, you visit the manufacturer's page and look for drivers for the exact model number of your printer, for instance, or your scanner or something like that.

And you will then check which versions of macOS are compatible with your apps and devices.

If you find that there is one version that is 100 percent compatible, great, you found one to upgrade to. 

But if none are 100 percent compatible, then you will need to look for alternative applications or hardware, and then you will make a list of their respective costs because it will give you an idea of how much it will cost you to do the upgrade.

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.

This will give you more time to do some research and also this will give time to third-party app developers and peripheral manufacturers to actually make their app and their drivers compatible with the version of macOS that you want to upgrade to.


Preparing For The Worst Case Scenario

Okay, so step number two is to take screenshots of all your System Preferences panes.

By doing that, you will keep a record of how your Mac and user account were set up. And if there is a small glitch during the update process, you'll probably be able to correct the issue by reconfiguring System Preferences properly based on the screenshots that you have taken.

Yes, this is quite a tedious process, I recognize, to go through all the preference panes, and you may never need it. But if you do, I'm sure you'll be glad you have it.

Okay, step number three is to make at least one backup of your Mac, preferably two.

The most obvious one is, uh, via Time Machine. And if you haven't configured it yet, now is really the perfect time to do so.

So you buy an external hard drive with at least twice the storage capacity of your Mac's internal hard drive, you plug it in, macOS will ask you if you want to use it for Time Machine backups, you say yes, you tick the option to encrypt the backup. Then you provide a password twice, and the first backup will start automatically, I think something like 3 minutes after that.

Okay, so now in addition to Time Machine, I recommend also creating a bootable clone of your computer. For that, I recommend buying an external SSD drive with at least the same capacity as the internal hard drive of your Mac. So why an SSD? Because it'll be fast enough to actually run macOS from it.

With a free utility called SuperDuper, you will be able to create a bootable clone. If you visit the website, you will see there is a paid version, but you only have to pay if you want to use advanced features like scheduling backups or doing Delta updates. But for what we need here, with the free version, it will be okay.

It will make a clone from your internal hard drive to the external hard drive, and it will be bootable, meaning that you will be able to start the computer from that external hard drive, meaning from your old setup, in case you encounter an issue after the update to the next version or the version that you decided to use for macOS.

Step number four is like for iOS. You need to gather all your most important passwords. So if you don't use a password manager, the first place to look will be in the Passwords tab of the Safari preference pane.

The second place to look into is the Keychain Access application that you can find inside the Utilities folder, itself inside the Applications folder. And there you will be able to search for your credentials.


Downloading the Installer and Making a Bootable Drive

Okay, step number five, now it is time to download the desired macOS installer.

To upgrade to the latest and greatest version of macOS, it's super easy.

On Mojave and later, you open System Preferences, then click on Software Update. It will tell you if there is an update. On High Sierra and earlier, you simply visit the Mac App Store and look for updates there.

But what if you want to upgrade your computer to a version that is not the latest and greatest?

In this case, you actually need a direct link that you can find on Apple support by doing a search. Visit support.apple.com and enter the name of the operating system you've chosen in the search bar. You will then see a simple process and a download link.

Before doing that, you may need to make some space on your computer because the installation process will require storage space. So, yes, you need storage space for the installer itself, but you also need more space for the installation.

For Mojave, for instance, you need to have at least 20 gigabytes of free space before upgrading from Yosemite or an earlier version.

One way to save space is to install a free application called OmniDisk Sweeper. With OmniDisk Sweeper, it will scan your hard drive and identify the folders and files that take up the most space on your computer. You can then temporarily move them to an external hard drive, for instance.


Initiating the macOS Upgrade

Okay, so you have enough space. Step number six is to initiate the update.

So once the installer has finished downloading, you have two choices. Either you proceed with the installation right away, or before that, you create a bootable installer and finish the installation process afterwards.

So if you only have one Mac to upgrade, then I would say proceed with the installation, because once you have installed the version of macOS that you want, it will be removed automatically after the installation process. But if you have more than one Mac to update, and again, maybe you also have a limited monthly bandwidth cap from your internet service provider, then this is where the bootable installer comes into play.

This is something that you create on a USB flash drive or a spare external drive with at least 12 gigabytes of available storage. So if you've got an old 16 gig USB key laying around, and without any mission-critical data on it, it's really 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.

So then, using the Terminal app, you will copy-paste a specific command from an article that Apple has provided. And this command will be valid for a specific version of the installer.

I've put links in the show notes with the procedure to format the USB key, and also how to create the bootable installer using the Terminal command. 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 have created the installer key, you will be able then to use it to upgrade your other computers and you won't need to download the installer from the internet multiple times.

Okay, so on the first computer, you just continue the process. The installer will update some files first, and when it's done, it will reboot, complete the installation process, which itself might require multiple reboots, until you see the initial setup steps.

For the other computers, you will plug the macOS installer USB key into the computer, and you will shut down the computer, and you will boot then from the USB key, and there you will be able to perform the upgrade of the internal hard drive.


Finalizing the macOS Upgrade

Okay, so in step seven, now you need to finalize the update. You may think, okay, now it has rebooted, I've done, it's finished.

No, it's not yet finished. Because you still have to go through the initial setup screens of the version of macOS that you just installed.

And why do you need that? Well, you need to configure some options, like Siri, dark mode, and maybe new features that Apple has brought to the Mac.

But then, you will also need to launch all the built-in applications, like Mail, Photos, Notes, Reminders, and so on, to see whether or not the database needs to be upgraded.

And this process can take quite some time, especially if you have multiple gigabytes of emails, a large photos and videos library to convert.

And it's not finished yet because you will also need to launch all the third-party apps that you rely upon, like Dropbox, Google Drive, Microsoft Office, the Adobe Suite, and so on.

Either you will need to re-authenticate yourself, so re-enter the password. Sometimes you will need to approve new restrictions that Apple may have put in place.

Now, if we talk specifically about macOS Catalina, you will need to explicitly give all the apps permission to display notifications, to access the Downloads folder, Documents folder, to access the camera, the microphone, the contacts, and so on and so forth.

So yes, Apple has strengthened the security of macOS Catalina, but really at the expense of a multitude of authorization panels that will show up the first time, the very first time that you launch an app. 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 um. If you're listening to this episode right on the heels of the release of Catalina, please know that some people have lost a bunch of emails because of a bug in the mail database upgrade process. And the problem here is bigger than just losing some emails locally, the deletion of the email propagated via the mail server onto other devices.

So that meant that the device that was upgraded to Catalina deleted emails or corrupted emails and this propagated everywhere.

Yes, so this is another example of why it is really 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 in a few months or I would say by the end of 2019 or the beginning of 2020.

Now talking more generally, you should have realized now that safely updating macOS is much more elaborate than what one might think. And it also takes more time if you want to do it properly and safely.

So like with the iPhone and the iPad, Macpreneurs should really allocate a weekend to update their Mac in order to minimize the impact of potential issues on their day-to-day operations.


Contest Announcement

Before concluding this episode, there's one more thing I'd like to mention.

If you are listening to this in August 2024, you still have the chance to win a one-hour Mac coaching call with me worth $200.

To participate in the prize draw is very simple: rate and review Macpreneur in Apple Podcasts by visiting macpreneur.com/review.

This will direct you to the show page. Scroll down to the bottom where you will be able to rate and review the show.

Take a screenshot and send it to me by email. The address is damien(at)macpreneur.com.

Hurry up, as you have only until August 31st, 2024, at midnight Pacific Time.

Beginning in September, I will randomly select one of you and announce the winner.

Once again, visit macpreneur.com/review.


Next and outro

In the next episode, I will kick off Season 6 of the podcast with an interview of David Shriner-Cahn, host of the Smashing the Plateau podcast and a community of the same name.

So make sure to subscribe or follow this podcast to get it automatically next week.

And until next time, I'm Damien Schreurs, wishing you a great day.

Thank you for listening to the Macpreneur Podcast. If you've enjoyed the show, please leave a review and share it with a friend right now.