I upgraded my 15” 2015 Macbook Pro to OSX Catalina (10.15) not long after it became publicly available, and now that I’ve been using it for awhile I wanted to share my experiences so others can decide if they’re ready to upgrade.

My Usage

First, though, you should understand a bit about my typical usage; that way you can identify things you’d use that I may not have tested. My primary day-to-day focus is web application development and Elasticsearch integrations, mostly working in NodeJS. Here’s a short list of dev tools and software I’ve used regularly on Catalina:

  • Docker
  • Elasticsearch / Kibana
  • Git / Fork
  • Homebrew
  • Mozilla Firefox
  • Node.js / nvm / npm / yarn
  • ProtonVPN
  • Slack
  • Tresorit
  • Virtualbox / vagrant
  • VS Code

When it comes to development I like to keep everything self-contained, repeatable, and specific to the current project I’m working on. This means I prefer using containers and VMs over installing software directly on my laptop, and this seems to play really well with the new security model in Catalina.

Here are some things that I have NOT tested:

  • Using / modifying built-in Apache webserver
  • Using built-in php
  • Installing / running a database server outside of a VM (MySQL / PostgreSQL / etc)

My Upgrade Method

I prefer clean installs to eliminate potential quirks from an upgrade, so this is the process I followed:

  1. Backed up all my files / configs (I use Tresorit for file sync/storage).
  2. Deleted most of my files - I noticed upgrades can be slow when you have a lot of data.
  3. Ran OSX Catalina upgrade.
  4. After upgrade, rebooted into recovery.
  5. Wiped hard drive, reinstalled Catalina cleanly.
  6. After install, restored my files and reinstalled needed software.

I use Homebrew for package management and rcm for dotfiles so restoring my environment doesn’t take long with a good internet connection.

What Works, What Doesn’t, and What’s Annoying

After a month of using Catalina I haven’t run in to any serious roadblocks, just some mild annoyances.

The biggest issue occurred the first time I tried to run software that hadn’t been notarized by Apple. At first it seemed like the program simply couldn’t be run - Catalina’s warning message simply said that the software could not be run because it could not be checked for malicious software (meaning it hadn’t been notarized). The only options presented were to confirm that the software wouldn’t run or move it to the Trash. This was misleading though as I soon found out any software can be run using one of these methods.

To open an unnotorized application on OSX Catalina:

  • Right click on the application and select ‘open’. In some cases the dialog box will now add an option to ‘open anyway’.

OR

  • Immediately after getting the notification that the application can’t be run, go to ‘System Preferences’ > ‘Security & Privacy’ > ‘General’. Under the ‘Allow apps downloaded from’ section, there should be a notice about the application you just tried to open and an option to allow it to run.

Another common issue I’ve run in to is granting permissions to applications the first time I use them - giving permissions for certain things sometimes requires restarting the application. This is most annoying in screensharing / call applications like Join.me and Slack where giving screen recording and accessibilty permissions requires a restart of the application, which you often don’t find out until you’re mid-call trying to use the feature. Luckily this is a one-time problem, once permission is given you are not prompted again.

All in all Catalina is stable and usable for my needs, your mileage may vary.

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