Upgrading from Mojave to Catalina

I’ve spent this weekend doing some maintenance on my Macintosh: organizing old photos into albums, upgrading various operating system patches, and finally upgrading from Windows 7 to Windows 10. Upgrading Windows was so wonderfully easy it reminded me about my difficult experience upgrading my Mac from Mohave to Catalina.

To set context, I run Windows in a VM on my Macintosh. Before upgrading, I simply made a copy of the virtual machine so that I had a direct path to roll back if things did not go well. I then ran the installer on the virtual machine. Windows was upgraded! It really was that simple.

So why upgrade to Catalina?

I have to admit there was a good bit of Mac fanboy wanting to upgrade to the latest and greatest operating system. The real driver, however, was a new feature called voice control.

Nuance, the makers of Dragon for Mac (screenshot right), stop support for the building of that product. While I didn’t love it, Dragon for Mac provided a meaningful solution to dictate on the Macintosh platform. Once Catalina shipped, it was clear why Nuance made their decision. I ran the upgrade wizard and within a few minutes, my Macintosh was running Mac OS 10.15 Catalina.

What problems started with Catalina?

Mojave was a great operating system for me. It was stable, fast, and made my mid 2014 Mac run well. All of that changed when I completed the upgrade. My Mac now felt slow, the fan ran constantly, and Lightroom labored with every switch of a photo. To say I was disappointed was an understatement. With a little experimentation I found out that disabling Voice Control decreased the running of the fan significantly however, my Mac still felt sluggish.

To complicate matters further, it took me a while to come to the conclusion that I was disappointed with the performance of Catalina or that at least Catalina would require the purchase of a new Mac – which was money I wasn’t ready to spend. I couldn’t just revert with Time Machine as I had a bunch of new work on the Macintosh I would’ve lost.

I came to expect a Windows machine needs to be reformatted about every 12 to 18 months so I had engineered the set up of my Windows machine to facilitate that workflow. All of the applications were on one partition of the hard drive and all of my data was on a different partition. I would simply wipe the C:\ drive and reinstall Windows and various applications while the D:\ remained intact.

I started using a Mac in 2009 and had never done a full format and reinstall. Sure, I had used migration assistant to move data from one Mac to the other. I’d used Disk Utility to format external drives and SD cards. I had not however used the Disk Utility to format “Macintosh HD.” It was really my first time issuing that fatal command on a Windows platform:

a:\> Format C:

The road backwards is bumpy!

Apple never intended for people to regularly downgrade operating systems. I had been living with Catalina for three months so reverting with Time Machine just wasn’t an option. I had to go through several bumps to get back to the operating system I left.

1. Create an external Mojave bootable drive

Disk Utility will not allow formatting the drive the active operating system is running on. Therefore, I had to create an external hard drive that was bootable with Mojave on it. This allowed me to format “Macintosh HD” and reinstall a fresh copy of Mojave.

2. Migration assistant for the not win

After installing Mojave I figured I could run the migration assistant to pull all of the data from my Time Machine backup into the latest copy of Mojave. This approach mostly worked until I started browsing the web. The migration assistant pulled over the Catalina version of Safari which would not run on Mojave.

Making matters worse Safari was a protected file so there was no way I could upgrade or shall I say downgrade Safari to a version that would work with Mojave.

3. Repeat step 1

4. Copy all my files over manually

Before formatting my hard drive I made a copy of my entire home folder onto a different external hard drive. After the second installation of Mojave I simply copied over my whole home folder back to the internal hard drive on my Mac.

Apple makes reinstalling applications from the App Store super easy. However, I forgot there were a couple of applications on my hard drive that weren’t available in the App Store. Tracking down those extra applications took some work, but I eventually got there.

A kudos to Apple

I purchased my Mac in December 2014. It’s not new by any stretch. To add insult to injury I was reverting an operating system upgrade. I wasn’t exactly the ideal caller for 1-800-MY-APPLE. Throughout my 3 to 4 calls to Apple support I got no pushback and the staff was more than accommodating to help me get back to functioning Mojave. Having that level of free support for a well out of warranty product doing something that likely isn’t sanctioned – kudos to y’all.

Hopefully the support folks at Apple were able to capture a few bugs off of my experience so that future users of the Migration Assistant won’t fault the same trap that I was in. The good news is my Mac is back to its former self running as good as it did before the upgrade!

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