Wish Me Luck Major Upgrade to Catalina

Subject says it all, been preparing for a while, updating SW, testing my LambTracker development on my laptop running Catalina, cleaning and organizing my emails, files, music library and cleaning up all the internal and external hard drives.

Today I will attempt the upgrade of my primary iMac from High Sierra to Catalina.

Just finishing my second full bootable backup (Murphy never sleeps) and then I’ll start the in place upgrade. I had planned to do a nuke and pave but have been convinced not to, at least as a first approximation.

Wish me luck!


What was your analysis leading to this choice, if it’s possible to discuss.

Good luck!

I upgraded to Catalina today (10.15.4), on a 2019 MBA. Spent the morning updating various apps, running Time Machine, and then made a Carbon Copy Clone prior to upgrade.

While fairly minor (on a scale of 1- Aperture), I’m still a bit miffed at Apple for their iOS 13 upgrade blindside to Notes and Reminders under Mojave. As for significant losses: Scansnap and Banktivity 6 will have to be run from a 2012 iMac that will remain on Mojave.

I’m hoping I’ve delayed sufficiently to avoid the pitfalls others have experienced in earlier releases. We’ll see how it goes.

I’ve been slowly cleaning up my High Sierra system iMac for several months. Started back in November and been cranking through updates, cleaning and renaming files etc since then. The saga of my email is well documented elsewhere but the annoyingly slow DEVONThink backup of my curated mail database is something I can live with for now. I still have some backlog of files and folders to clean up but most of the system was clean. I had also been deleting old versions of software installs and removing old apps. I used to keep all the installers for every app I use for at least 2 revs, current and one before. That was due to relatively slow download speeds. But with fiber to the house and a nice high speed link I decided I could eliminate most of those. I still keep backups of my critical app installers as an OSBU (oh S**t Backup). Those are DEVONThink, Onmifocus, 1Password, Scrivener, iMazing, Scapple, LightRoom and the old version of Firefox I use to do SQLite database management and query testing. Everything else is not so critical that I can’t wait and download a few days after disaster, if it happens. So I felt my machine was relatively clean and I might get away with it.

I usually get the “Take Control of Upgrading to” books each time just to have a nice checklist of things and make sure I don’t forget anything. I often skip versions so need to get caught up on changes. For example, I never ran Mojave on any of my machines. Most of the time the recommendation has been to do a clean install or a nuke and pave. Both Mojave and Catalina were the first ones that suggested doing an upgrade in place and I felt I’d give it a try. I could always go back to the clean install or nuke and pave if it didn’t work.

What I was not entirely prepared for was the 30+ hours it took to make 2 complete bootable backups. One for my offsite BU and one for use in case I have to roll back. The actual install took about 6 hours to complete but went on without any major hitches or issues.

I then immediately got mail running and to my dismay had well over 600 messages to handle and none of my mail rules were working. Spam sieve was not enabled so they all ended up in my inbox. It took a while to get everything running properly and I’m only just now, several days later, am I getting my email inbox down to a dull roar. With the COVID-19 stuff my normal 200+ messages a day has jumped to 500+/day. People spending time at home have time to ask me hundreds of questions. Plus most of the Black Welsh flocks are lambing and I’m getting my usual how do I register or birth notify lamb questions from new folks. Spam is through the roof and even though I’ve got Spam Sieve working now I still have to review every spam message because I’m getting between 1-3 good messages caught as spam every day.

A lot of my regular software was not up to the current rev. I couldn’t upgrade it while I was still on High Sierra because the new revs didn’t work on HS so I’ve been slowing verifying and upgrading every app I own. It has made me realize some of the older ones I no longer used but missed in my cleaning and I’m now deleting all of them as well.

So far I haven’t found anything that doesn’t work at all except SplashShopper and the developer won’t upgrade it. I’m working on my own personal replacement and I actually scored the source code to HandyShopper from Palm days that I’m going to take a look at sometime later this summer. HandyShopper was great and SplashShopper was very similar. I knew going into this that SplashShopper would not run so it wasn’t a surprise.

A few glitches, se the MPU icon issue in Safari thread but overall it’s working as expected.


Thank you. This is a very helpful recap. I appreciate the time you took to put this chronicle together :+1: