My Upgrade To macOS Catalina

Two weeks ago I did my upgrade to Apple’s latest and greatest OS which is macOS Catalina. Because this version of macOS is different than macOS updates, I thought that I would take a few minutes to walk you through the upgrade process and why I went approached it the way I did.

First of all, I didn’t dive into this upgrade the second it became available. Instead I waited for two things to happen:

  1. I wanted all my apps that I rely upon to have 64-bit versions available. That’s important as Catalina only runs 64-bit apps and 32-bit apps will not work at all. If you want to find out what apps are 64-bit or 32-bit on your Mac, this article will help with that. Most of the software that I own was already a 64-bit app. But my invoicing software which is Express Invoice for Mac wasn’t available as a 64-bit version until three weeks ago. So I had to wait until that happened before I could upgrade to Catalina That’s pretty bad as app developers had Apple warning them for two years to prepare for the demise of 32-bit apps. Thus you could make an argument that the company who makes Express Invoice was asleep at the switch.
  2. Even if my invoicing software was ready to go, I wasn’t going to upgrade until the first update to Catalina appeared. That’s because of Apple’s recent history of initial macOS versions being buggy. A perfect example of this is how Apple broke WiFi a few years ago and it took them forever to fix it. You don’t want to be in the middle of something like that if you don’t have to be. So when the .1 update appeared, and I heard good reports about it, that’s when I decided to make the jump.

My first step was to make sure I did a back up of me current setup so that I could roll back if I had to. I use Carbon Copy Cloner for my backup needs and I created a disk image backup on my NAS that would facilitate a roll back if the need arose. Then I ran the installer for the OS, which strangely (at least to me) is in the software update section. The install of Catalina was quick and after some quick testing, everything was almost perfect. I had two minor problems:

  • I found a “Preboot” folder at the root of my hard disk after upgrading to macOS Catalina. This is usually hidden so that the fact that I see it is a minor problem. And deleting it is a really, really bad idea as you would leave your Mac in an unbootable state. Fixing it was a bit of a pain in the you know what. I’ll tell what I did to fix this. But what I will say is that this is NOT for the faint of heart:
    • First I had to reboot and disable System Integrity Protection. This is a feature of modern operating systems that protects the OS from being affected by malware. There’s usually no good reason to turn this off, but in this case I had to using this method. Note: You will have to authenticate using an admin account to allow you to disable System Integrity Protection. That’s a new security measure in Catalina.
    • Once you reboot to get back into Catalina I had to go into Terminal and enter: sudo mount -uw / as this makes the system volume writable (which is read-only by default since Catalina so that the OS is protected).
    • Use this command to hide the Preboot folder: sudo chflags hidden /Preboot*
    • Re-enable System Integrity Protection
  • Carbon Copy Cloner apparently didn’t like the disk images that I had made for backup purposes. Thus I ended up deleting all (with the exception of the one that I made in case I had to roll back to my previous version of macOS) of them and making new ones. It also allowed me to shrink the size of these disk images so that they take up less space on my NAS as saving disk space is always a good thing.

So how is Catalina? For the most part I like it. The things that jump out at me are:

  • Some people described Catalina as “Windows Vista for Mac” as it will prompt you to allow or deny actions such as notifications or access to hardware like cameras. Plus it has options buried in the security preferences pane to allow you to customize access for apps. In my case, I saw a brief flurry of requests to allow or deny behaviors related to some apps after the Catalina install, and have seen maybe two requests since. So I think the whole Windows Vista thing is overblown. Besides, I would rather have more security with some inconvenience than less security with ease of use.
  • I like that you can now use the Apple Watch to not only log into your Mac, and to pay for stuff, but you can also use it to allow certain security related actions. Hopefully Apple expands on that.
  • It does not seem any slower than macOS Mojave so far.
  • The removal of iTunes and the use of the finder to sync your iPhone is a total non-event. It works exactly the same way. Though for me to get WiFi syncing working, I had to turn off WiFi Sync, reboot, and turn it on and reboot again before it worked.
  • There’s a Photos app that organizes pictures by day, month, or year, while also intelligently choosing your best photos so you can relive all of your favorite memories. It took all night of processing to get that to work as I have thousands of photos, but the results are good.

So should you update to Catalina? I would say that there is no reason to sit on the fence any longer. As long as you have a backup and you have 64-bit versions on the apps that you rely on, you should be safe to dive in.

2 Responses to “My Upgrade To macOS Catalina”

  1. Still going to wait for 10.15.2

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