I recently upgraded to Catalina on my Macbook Pro and unfortunately, this is the first time I had some issues doing a macOS upgrade.
First is the installation process itself. I always opt for a clean install using a USB drive, it’s a way to get rid of the clutter on my Mac. This time though, I had my first attempt freeze and I had to restart my Mac. I personally get paranoid about things like that, so I had to repeat erasing the drive, and starting the install process again.
Second issue I had was my iCloud Drive did not sync immediately. If you view it on the Finder, my iCloud Drive would only show empty Desktop and Document sub-folders and with an iCloud icon that indicates “Waiting for upload”. I did a quick search on why this happened, and found others who experienced the same issue. Sadly, the solution was to just wait.
The last issue is that my Apple ID could not sign in to both Music and TV apps. If I enter my Apple ID credentials, nothing happens. Another quick search shows that this is another known issue, and the workarounds are annoying to do (1, 2). Apparently, not signing in to your Apple ID during the Catalina installation process is a way to avoid this problem.
I’ve never been one to be cynical about Apple’s software quality but this is very disappointing.