macOS Catalina: 'More trouble than it's worth'?

Interesting blog posts from Riccardo Mori, from October, and with a follow-up this week.

"The amount of feedback I’ve received about Catalina
in the past few months is staggering, to the point that
I have created a dedicated folder in Mail to collect all
the messages that keep coming on a fairly regular basis.
They’re 83 so far and — spoiler alert — 98% of them are
complaints. The remaining 2% are neutral."

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This one is so strange to me. The beta for Catalina had some rough spots, but for me most of those were related to iCloud sync issues–particularly on Notes. Looking at the beta feedback that I submitted, I also had a problem with Books constantly asking me to enter my AppleID and password. Lastly, I had some strange issue not being able to drag an e-mail from Mail into the compose window of a new message as an attachment. There were some other issues involving 3rd party apps, but those were just a function of things breaking and needing to be updated by the developers.

Since the official release, I have experienced no problems that I can attribute to Catalina. I know the security process has gotten a bad rap, but I think the comparisons to Widows Vista are grossly exaggerated. I lived on Vista for four years (which was a big part of why I migrated to Mac to begin with). It was torture, and the security model was excruciatingly painful. (I never did understand what a Roaming directory was, what it did, why certain of my apps couldn’t find it, and why it was not automatically included in backups, but I digress.) On Catalina, you have to approve more things than on Mojave, but once approved the OS doesn’t continue to ask you repeatedly for permissions.

I’ve spent more time in front of my Mac from about early October to now than I have in years, and I have zero complaints related to bugs, unexpected behaviors, unwelcome behaviors, or what have you.

I like Catalina. This is just one guy’s experience, but I do find it surprising that my experience has been so smooth and so many others are seemingly having a miserable go at it.


This is a good example of selection bias. “98% of the people at the swim meet enjoy swimming, the other 2% were too young to respond.” “100% of people at the peanut festival did not have a peanut allergy “ etc.

tw: science
The math doesn’t work out either, 98% of 83 is 81.34 people. 2% of 83 is 1.66 people. (People are normally measured in whole numbers.)


As usual, when upgrading, some minor issues. I am not going to blame Catalina because vendors were late in the game with 64 bit updates. I was able to sort out every one of those minor issues within 1-2 weeks.

Since then, no issues. But I didn’t send out emails or wrote posts “I upgraded to Catalina and life goes on”.

My prediction: it doesn’t matter at all what the next version of macOS (“Venice Beach” with hip design, “Alcatraz” heavy on security, “Hollywood” with added video stuff, “Redwood” extra stable) will bring, 98% will again complain (“everything broken”).


Whole numbers are entirely rational whereas people are frequently irrational and sometimes even imaginary :slight_smile:


I first adopted Catalina late in the beta release and have been happy. As others have said it was a bit bumpy in beta but I have had no notable problems beyond having to find solutions for a couple of 32 bit apps that were part of my regular routine since the official release. No complaints here.

Definitely some negative roots on the planet.

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The Security issues are really over the top. It’s like a household safe so hard to open that even the owner has a difficult time doing so. It borders on paranoia for such a degree of “security” to be mandatory for all users.

Nah, as long as you don’t need 32bit apps and don’t mind getting forced to upgrade some apps to subscription model it’s all fine.

You get used to the extra step to give apps permission it’s fine.

Remember that negative news about Apple sells.

What things are happening when you use Catalina that make you conclude this? You’re not the only who has asserted this proposition, of course. But nobody seems to do much more than make the pronouncement.

I’d also like to know what’s the problem with security? The OS asking for access for apps the first time you use them? And BTW, being “paranoid” is exactly the right mindset when it comes to security.

I’m not sure what I get out of Catalina. But I know CleanMyMac 3 didn’t work with Catalina and I’m forced to try CleanMyMac C, which is a subscription base. I’m not happy.

No, there has always been a one-time purchase option, and upgrade option.

18 months ago I purchased the $44.98 upgrade (compared to the $34.95/yr subscription), three years after buying CleanMyMac 3 upgrade for $19.95 (after essentially getting it for free in a 2013 MacHeist bundle). It’s a good product, it’s well-supported, and the upgrade pricing has seemed fair to me. And when I made that 2018 upgrade to the current version I was also sent a non-expiring coupon-code for 30% off any of their other products. An unexpected surprise, a nice lagniappe.

I see their subscription pricing as a strong hint for people to consider their SetApp subscription product, as SetApp contains all their apps plus several dozen of the highest-quality Mac apps around, for a very affordable overall price. (If I didn’t already own most of the SetApp apps I’d want I’d jump at it.)

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Here is an example -

Every time I use the Devonthink 3 web clipper I am presented with this question:

It would be fine if I had to grant permission once and have it remember my approval of the web clipper. But that is not possible - I have to add this step every single time I use the web clipper.

Devonthink development has concluded that the problem is at one point when I installed Catalina, I answered “no” when presented with a security requesting offering Devonthink this permission. If I did not grant the permission then, there is no way to go back and change that decision short of doing an entire re-install of Catalina from scratch. Some of the new security settings cannot simply be changed by the user ad lib; they can only be changed when the query is presented to the user, and that may occur only once during the installation of the software.

More details here:

and especially here - a related security issue:

Not if “security” locks yourself out of your own home.

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Where am I locked out of?

DEVONthink web clipper is constantly locked out unless I give explicit permission every time - no way for me to change it.

Reminders script is permanently locked out of DEVONthink - script can only be run externally

That would be annoying to have to approve the web clipper every time you use it, especially if you use i multiple times a day. You are reporting this here as a Catalina problem. But when I read your post about the web clipper in the Devon forum that you linked, it looked like you have been having this problem since you were on Mojave (macOS 10.14.6). Or did I misread the post?

There are lots of DevonThink users here, I wonder if any of them have confronted this? I understand, for example that @OogieM is a faithful DT user, but I don’t know if she’s upgraded to Catalina. I also don’t use Chrome so I can’t speak to that.

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I agree, and I say this as someone who’s job is managing information security. Although it’s something of a paradox, “paranoid” thinking is generally counterproductive to effective security.

To keep this on topic: I was recently working on my MBP while out of the office and on something that would have benefitted greatly from having a second display. Swiping back and forth between spaces was fine, but not nearly as nice as having two displays. Then I remembered Sidecar, pulled out my iPad, and within 20 seconds (really) I had my second display, a Catalina win :slight_smile:


Correct - the problem started with 10.14.6. I mention it as a Catalina problem because Catalina has required similar mandatory security permissions to an even greater extent than Mojave did. But perhaps the problem would be better stated as related to the recent increased requirement for apps to request security access which is an evolving an increasing trend over multiple macOS versions.

The bottom line is that there exist macOs security settings that can be changed only if the user is prompted to do so, and for some reason in some apps the user only gets one chance to grant that permission, with no way for even the developer of the app to allow the user a second chance.