Image: Apple Inc.

Some OS releases are better than others. macOS Catalina? I don’t believe the operating system’s introduction is Apple’s finest moment. Let me count the reasons why not.

In fact, I began encountering trouble even before Catalina, macOS version 10.15, was released October 7, 2019. Apple readied iOS 13 first, which I dutifully loaded upon release September 24, 2019. Subsequently, for two weeks I was presented with recurring errors in which critical Notes and Reminders, updated on various iPads and iPhones, failed to synchronize to my primary Mac. Confusion and frustration resulted, impacting and interrupting daily production, as no practical fix was available until macOS Catalina hit the streets. If I had known the trouble would arise, I would have waited to update my iPhones and iPad.

SEE: Top 20 Apple keyboard shortcuts for business users (free PDF) (TechRepublic)

Problems with the macOS Catalina installation

Even the macOS Catalina installation proved problematic. Sufficiently experienced to recognize one should never interrupt an OS installation or macOS update in progress, or hard reset a Mac installing a new release, I was required to do just that.

After staring at the Setting Up Your Mac screen, and watching the corresponding Setting Up twirling cursor image for hours, I was forced to search for others’ experiences with the same problem. I immediately found I wasn’t alone. Numerous users were complaining online about the same problem, with the only readily identifiable guidance being to interrupt the install by depressing and holding the Mac’s power button. Fortunately, the macOS installation proceeded after doing so, but there were anxious moments wondering whether I was going to have to recover all my data from a local Time Machine backup.

Once macOS Catalina was installed, I presumed trouble related to the new OS was over. I was wrong.

Problems after the macOS Catalina installation

If my Mac were a car’s dashboard, the equivalent of multiple warning and check engine alarms displayed upon booting. Apple ID, iCloud, and related features generated alerts. Previously validated services, such as a remote desktop connectivity application, aggressively and repeatedly generated failure pop-up windows. I had to invest time navigating System Preferences Security settings and re-enabling these applications’ behaviors, even though these applications had already previously been configured.

Then I turned my attention to Mac and Apple passwords. The Apple ID window repeatedly popped up requiring a fresh login, which upon completing, continually re-appeared. Frustrating. I expect better from Apple. The issues reminded of similar experiences so often associated with Windows, the very ones that prompted me years ago to convert to using a Mac as my daily production platform.

Ultimately, I traced Apple ID, iCloud, and local computer login errors to the need to change my already complex passwords to new entries. Changing all the passwords, both local and cloud-based, was the only solution I found to work.

SEE: macOS Catalina: Avoid my mistake and wait before you upgrade (ZDNet)

With those issues resolved, I encountered more trouble. Photos were no longer synchronizing and, as a result, new images were missing. After much trial and error troubleshooting, the only solution I found to work was logging out of iCloud completely and logging back in, a process that literally required days for the corresponding photo and file downloads to complete.

I also found Apple Pay and associated credit cards no longer worked on my Mac. After several attempts, in which I received only an innocuous error message stating the action failed because the Mac security configuration changed, I discovered the solution was simply to open my Mac’s lid while re-enabling the feature. Mind you, the lid didn’t need to be open for Face ID or fingerprint authorization; the lid just needed to be open.

Meanwhile, on a deadline to perform a Windows-specific task, I found my VMware Fusion 11 virtual machine no longer worked. That’s a frustrating discovery to make at midnight the evening before you go out of town. While that’s not Apple’s fault, the problem was due to a macOS Catalina incompatibility with previously installed software that operated flawlessly before the macOS upgrade was installed. Following a free VMware upgrade to Fusion version 11.5, I was back in business, but the overall process was anything but smooth.

The bottom line

Apple boasts a long track record of elegant operating system upgrades. But as these issues—most all confirmed to be widespread—indicate, macOS Catalina wasn’t quite up to those typical standards. Hopefully, future releases prove to be more polished.