My Catalina Upgrade

Hello there,

This is about my Catalina upgrade. I was on the road when it dropped and I do not control the upgrades on my work Mac.  So at home now and time for the upgrade.  I like very much Catalina as I have been using it for a while in beta.

Learning / Links

  • Here is an excellent video on it. Reminds you well of the new features.
  • Here is a good article
  • Here is another article that looks at things a little different.
  • Another article that is good too.
  • Here is a review of it by PC Mag.
  • Here is an article on the 8 hidden features of Catalina.
  • Here is a good article that will help you with sync type activities in Catalina.
  • Apple’s List of 235 Apps that are not compatible with Catalina - here - not truly an easy list to go through.  My test above about checking for 32-bit apps is the key thing to do.


  • I do a Time Machine file backup, as well as an image backup using SuperDuper.  Do not want any issues that I cannot recover from. Yes, I know not likely but still like to be careful.
  • I also confirmed I have no 32-bit apps. You can check this by:
    • About this Mac
    • System Report
    • Now select Software, and Aplications.
    • You should not see any No in the 64-Bit Intel column.

  • I suggest you visit some of the links above.  iTunes is gone so you might wonder how to sync your iPhone.
  • This update is one of the longest I have experienced so leave a good amount of time aside for it.

Release Notes

When I went to upgrade, I say where it said more info, and I thought htat would be the release notes.  But, instead, what I got was this article. Some nice info but not really release notes.


So I see the red 1 in the Settings app.  So I open it and select Software Update.

  • So we use the Upgrade Now button.
  • The upgrade appears to be 8.09 GB - which is a pretty good size!
  • I have a fast internet connection so it doesn’t take long to download.
  • Next I see the install screen.

  • So continue, and make sure you have the right drive selected.
  • You will be warned if there is any apps that will not work due to the 32 bit lack of support now.
  • It will take approximately 20 minutes (on my newish MacBook Air).
  • It will restart, and it will be a bit slow. It will have a couple of restarts, and then it will take about 25 minutes. Actually, in my time it was more like 40 minutes.
  • It will be turned off when done.
  • Turn it back on!
  • You will get a few questions.
  • Now I get to my first issue.  When I am asked about Screen Time, which I don’t care about I say to Set it up later.  But then I cannot get past that screen.  But after several minutes it just went on by it self. No harm. (and one time it did not go on.  I hit power off and then power on and all good).
  • Next is the Setting up Your Mac screen. Which must be a bigger job than I anticipated due to the time I stare at that screen! I did not time it, but it did take quite some time. Not sure why, but I suspect this may be something that may vary for people. My drive is already APFS, as well as encrypted so that is not happening but maybe it is slowing things down? This step is over three hours now.  I should have timed it. So I was distracted by an amazing dinner my wife did, so I did not check until morning.  And it was still doing the setup.  So I powered off and back on. I logged in, and things appeared to be OK.  I was prompted for a Catalina overview, and to allow some notifications. I had to authenticate with the cloud again. I answered the questions on notifications, and authentication, and I restarted.
  • I had to log in several more times into the cloud.  Even after the restart.  So I logged out of Cloud and back in again. I had this issue with my iPad / iPhone after upgrading to 13.x.  There, I got past it by saying cancel! The log out, and then log back in did fix the issue as I was not prompted any longer. BTW, be aware that when you log out, and log back in to the cloud, you will need to download documents and pictures again.


  • The first thing I look for is my reward info still on the login screen before I log in - and it is.
  • Can I log in using the account / password that is correct - Yes.
  • The next thing I like to check is email.  Can I send and receive - Yes.
  • Does the new Find My app see my devices? My wife - yes. Her picture is not seen.  In the old version, and on the iPone it is.
  • Does my Horizon View client (v5.2.0) work - Yes.
  • Does BusyContacts (v1.4.1) and BusyCal (v3.7.1) work - yes.
  • Does Evernote (v7.13) work - yes.


This was the longest and hardest upgrade for macOS in recent memory.  However, no data was lost, and no functionality was impacted so it ended well.  But it certainly could be improved.  I am happy I am on Catalina now for certain.

I am not sure if this update is for everyone.  My wife updated when I was not looking, and it was a little faster than my update.  I think most people that are not really into computers, but rather think of them as tools, maybe wait a bit to update.


  • 2/8/20 - I did this on another mac, and on the Screen Time screen I said do it later but this this time it did not go on after a few minutes.  I hit the power button, and everything came back fine.  Still connected to iCloud, proper screen background and more.  All good.
  • 10/26/19 - I have been using Catalina since it dropped and I am very happy with it.  I have not experienced any issues. I know you might have issues like 32bit apps but I did not so I am very happy.


=== END ===

2 thoughts on “My Catalina Upgrade

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