macOS 12 Monterey Upgrade Issues

Originally published at: macOS 12 Monterey Upgrade Issues - TidBITS

While our general advice to hold off on upgrading to macOS 12 Monterey remains in place, Adam Engst shares some thoughts on why Monterey may merit an earlier upgrade than previous versions of macOS. But he also points to some upgrade problems that suggest that we’re not quite there yet.


Mr. Macintosh is talking about upgrading to Big Sur, not Monterey and the link provided references a directory that doesn’t appear to exist in Monterey. I have updated three systems - MBP16, iMac Pro and iMac 21 (Intel) - and all updates went fine.


My Late '14 Mini updated to Monterey (from Big Sur) without any problems. I did not disconnect my external drives, even though I know you’re supposed to do that before updating. (My bad!)

I tried Live Text by taking a PDF I had of a document in Italian (needed for my class this semester), making a JPG of a page, and then -trying- to get Live Text to see and translate from Italian to English. No Go. Very disappointed with that!

My new MB Pro 16" last reported location was Anchorage. I presume it’ll arrive Monday as Apple promised (rather than tomorrow, as UPS -originally promised-. But there’s a chance it could arrive Friday, depending on where it goes to next. I’m in New Hampshire.)

Plus, as Howard Oakley notes, Apple seems to be focusing its bug fix and security attention on Monterey over Big Sur and Catalina.

I don’t think that’s a correct way to paraphrase what Howard was getting at.

His argument is that Big Sur is likely only getting security patches from here on out. So staying on Big Sur and delaying Monterey should not expose you to any specific security risk. But you will most likely be left without non-security related fixes which can, as he points out, be “damaging to workflows or downright annoying”. Let’s note he is not saying Apple has removed security attention from Big Sur (yet).

1 Like

I am a bit confused on the release dates.
I enrolled a Mid 2015 MBPro system in the Beta (developer?) program well before
Oct 25, 2021, (in July actually) only lightly, dabbled with Mac OS Monterey
with no notable issues.
I blithely updated to 12.1 Beta last week 11/29… at that time the Beta version was in the App Store.
I notice today that the App Store offers Monterey, no v. listed … presumably out of Beta.
What happened between a safe Beta and this problematic official release?

macOS Monterey 12.0 shipped with the new M1 Macs late last month, but a 12.0.1 update was released as RC2 to beta testers on 10/21 and to the public on 10/25.

Beta testers generally aren’t the ones reporting these problematic issues, rather it’s coming from mostly from regular users who were running Mojave or Catalina and a few Big Sur users. There were some Beta testers that had the same issues back in the summer, but those mostly forgotten over the following months. A group of about 200 Enterprise IT’s didn’t forget and got together to find the root cause which they have communicated to Apple and gotten a promise that it will be fixed in a subsequent update (I would guess 12.1).

1 Like

While my adventurous nature and tendency to be an early adopter had caused me some software compatibility issues in the past, I must confess that the upgrade of my 2019 i9 MBP16 from 11.6.1 to 12.0.1 went smoothly. Not only that it was relatively quick (disregarding the long software download that happened in the background and did not affect my work), I am also yet to discover a single application (out of those I regularly use) that misbehaves. Maybe it is the 1-week wait before performing the upgrade that allowed 3rd party software developers time to fix any incompatibilities and release the necessary updates. All in all a clean upgrade and so far a solid and stable release.

My first concern was, obviously, ensuring two applications work as they should:

  • Cisco AnyConnect to ensure my VPN to corporate HQ works.
  • Microsoft Outlook for my e-mail and calendar. Yeah… Yeah… I know… It sucks but did I mention “corporate” in the previous line?
    So - they both do. I checked the Berkeley compatibility report and held off the upgrade until I saw the green light (or rather green V-sign) on their site.
    Then it was the Video-Conf tools I use: Zoom, GoToMeeting, Teams. All work well.
    The rest is easy: The Apple stuff (Safari, Final Cut, Logic Pro) was nothing to worry about, the Microsoft Office and Adobe stuff are both so widely used that if there were any compatibility issues they were resolved during that 1-week wait, and I saw nothing of them.
    The lighter tools scuh as Fantastical, Keyboard Maestro and some of the technical diagram design tools (Camunda, OmniGraffle) all issued updates during that week and were stable after the OS upgrade.
1 Like

Thanks for this Adam, the installer is sitting in my Applications folder. I’ll hold off a while more. Most of my critical apps, Capture One, DevonTHINK, Notion, various image editors are updated.


Talk about tunnel vision! I was so heads-down in Monterey issues that I failed to notice that key fact. I’ve recast the article now to address that error.

We know Live Text has fairly specific system requirements on iPhones and iPads (A12 Bionic or later). Apple didn’t specify any such requirements for Live Text on Macs, but perhaps there are some.

Hmmm. In that article, he seems pretty clear about how the security fixes are not equally distributed, saying:

Last week, though, the penalties with staying on Big Sur or Catalina were spelled out in starker terms: if you want all the latest security fixes, then you must run the current release of macOS, as older versions, even though still in security maintenance, don’t get them all.

Many of us had already suspected this to be the case, but it was the careful analysis of last week’s upgrade and updates by Josh Long @theJoshMeister, Chief Security Analyst at Intego, which provided the damning evidence: more than 20 of the vulnerabilities fixed in 12.0.1 have been left unpatched in 11.6.1 and Catalina Security Update 2021-007

I don’t think for a moment that Apple’s security engineers are deliberately withholding fixes from the two previous versions of macOS to ‘punish’ those who haven’t upgraded to Monterey. It’s far more likely to be a simple matter of cost and benefit. Fixing some of the known vulnerabilities can require considerable effort, in some cases as much as rewriting substantial parts of the kernel or one of its multitude of extensions. If the perceived benefits are low, and the costs of implementing a fix are high, it’s only understandable that some only make it to the current version of macOS. Apple’s priority is quite reasonably to ensure that Monterey is as good as it can make it.

I can confirm that Live Text does not work using Danish.

I made an example photo with some Danish text, but have the same results using English texts on photos.

Using Danish as primary language, no character cursor ever comes up in neither Photos nor Notes, but as soon as I change the primary language to English , text suddenly becomes searchable (in Notes at least), and select-/copyable. Even Danish text… a rather silly missing functionality.

Oh man, I’m reading too fast these days. @deemery was talking about Italian text, which Live Text explicitly does not support at this point, so my comment about the system requirements was misguided.

Now, your point that Live Text doesn’t even work on English text if the primary language is set to something other than a supported language is well-made—that does indeed seem like a silly limitation. Why not detect text in a supported Live Text language regardless of what the system language is set to?

FY amusement: A friend has some OCR programs left over from a project where he’d run stuff through multiple OCR and then ‘vote’ on the results to improve accuracy. I sent him the PDF of the paper in Italian. Then I took the results from the best individual program (rather than the weighted average), and then page-by-page, I pasted the Italian into Google Translate. I read the English results, and where things made no sense, I went back and fixed the OCR mistakes. This produced something that was good enough for my purposes (understanding the paper), even if it wasn’t a perfect line-by-line translation.

1 Like

Well, it actually picks up both English, German and Danish, when the system language is set to English, in my brief test here. And somehow it works better in Notes than in Photos. (perhaps it is still indexing, though)

This does sound strange. Since we’re talking about image-to-text conversion and not translation, it seems to me that this should be a function of the language’s alphabet, not the language itself.

Anything using Latin characters (plus accents, of course), should work equivalently, since it is ultimately all going to use the same engine.

On the other hand, languages that use a different alphabet (e.g. Slavic, Hebrew, Arabic, Chinese) will require a completely different back-end.

I can understand having the system only support one back-end at a time, because it could be a large CPU load to test every image against every supported alphabet, but I still think all languages using (for example) the Latin alphabet, should be supported at once.

Doing text recognition in a different language, even with (almost) the same alphabet is not an easy task, so that is at least a probable cause of the missing languages - and then doing simple character recognition in whatever text is present makes sense. I have just checked that the Danish characters æøå fail to be recognised, even though the text seems fine, as well as most Polish, where some letters like śą or ł don’t show up, but it picks up German characters pretty well, even without German as the primary language (it is my 3rd language on the list of languages that I use)

1 Like

I guess this is more of an Op-Ed: Not to be argumentative but shouldn’t we be a little bit skeptical with regard to cost benefit in regard to maintaining support for “older” systems?
In the past Apple did support up to three systems, with aplomb. While, of course, the engineering skills on this are way over my head, I have a hard time being convinced that the burden of the cost seriously hampers this trillion dollar company.
Especially when it appears their engineering dept is a tad bit casual about bricking “old” computers
Things are really being thought “different” when a 2019 or 2020 Mac system is considered old

1 Like

I’m often tempted to think that a trillion-dollar company can do just about anything as well, but the Mythical Man Month does come into play here. You can’t just assign more resources to some tasks to finish them sooner, and as the test matrix increases, the amount of work goes up much faster than linearly. That’s especially true when there is specialized knowledge that’s required to complete the task, as opposed to something where more bodies are really all that’s necessary.

And as David Shayer pointed out when iOS 13 and Catalina had such problems, we’re dealing with vastly more complex systems than in the past. Making even small changes could (and often does) cause other bugs, so there are tradeoffs to consider in every change.


Thanks. I hadn’t read that article (it was posted before I started reading TidBITS).

The lack of automated testing is very surprising. It is simply not possible to thoroughly test something as large as an operating system without it.

I remember reading, back in the 90’s, how IBM used automated testing to greatly improve the quality of their OS/2 operating system. Their policy, according to the article, was that after fixing a bug, an engineer was required to develop an automated test in order to demonstrate that the bug was fixed. The full suite of automated tests were configured to run as a part of a nightly (or maybe it was weekly) build process. So any regression could be immediately detected.

If Apple isn’t doing something like this system-wide, then I would consider it a very big mistake. They should have an in-house data center full of Macs (or at least servers running macOS in VMs) that can constantly run regression tests as a part of their internal CI strategy. A core set of tests to run after every code check-in, a broader set to run every night and the complete set running at least once a week.

And if they’re not using some form of CI, they need to start. There’s no excuse for not using it on a large project today.


I have heard that some systems for doing OCR use neural networks and operate at a higher level than individual characters, such as words. In that case I guess every language would need its own engine. But I have no idea whether Apple is using that.

thanks for the referral.

I could not help wondering as I read through the various sections whether at its core
the questionable reliance on the (clockwork): Annual Mac OS Upgrade looms as the major problematic element