Wednesday, October 16, 2019 [Tweets] [Favorites]

Catalina Vista


Tyler Hall (tweet, Hacker News):

I completely realize and wholeheartedly own-up to the fact that I’m a geek and a Mac power user above and beyond what normal muggles will ever experience, nonetheless, this is the first-run experience I was greeted to this afternoon after upgrading to Catalina.


I only spent about ten minutes on that system today. But it was enough time to capture all of these papercuts and combine them into one truly-awful über screenshot.

I want to make clear that I’m not blaming the talented Apple engineers who obviously worked their butts off on Catalina just like they do every release.

My side-eye is squarely directed at the managers and Marketers who push for such an insane release cycle.

Sean Heber:

Just installed Catalina and logged in for the first time and have been hit with 6 permission prompts for various things so far.

Ben Sandofsky:

Your first time running Catalina:[…]


Apple seems to be forgetting their own credo against nag-based security


I’m astounded with some of the user security dialogs that Macs display. I got one today: “VSCode wants to make some changes. Deny or Allow.” That was the exact wording.

Matt Birchler:

Can Apple reimburse my company for all the time I’ve spent authorizing apps to perform basic functionality on my Mac today?

Joking of course, but man, this feels like Vista to me. Do a thing I do every day…“do you want to do this?”

I support the move to make the Mac more secure, but this is a rough first run experience.

Dave Wood:

Thanks for wasting more of my time #macOS #Catalina. Seems cron jobs don’t run anymore if they touch certain files/folders, including your ~/Documents folder (even if your script is stored there).

The system should be prompting for access to that now-protected folder but isn’t.

Dave Wood:

Solved the cron permission issue properly: drag /usr/sbin/cron into Full Disk Access in System Prefs.

Steve Troughton-Smith:

Everybody’s complaining about Catalina getting in the way of the command line and I’m like you know you can turn off SIP, right? Everything goes back to the way it used to be; I’ve never seen aaany of this. If you want the legacy security model, you can have it

Dave Wood:

The problem w/doing that is that I won’t see problems that my customers will run into. I need to swim in the same cesspool first so I can find out how to get them through it.

I bet a bunch of Apple engineers have done this exact thing & thats why we’re in the boat we’re in now.

Phillip Boushy:

There are so many other security controls that SIP implements that disabling it is overkill. Apple should have given a better UX for this. Make them entitlements if needed, pop up a single window during first load. Also an “allow all apps access to X” would be nice...

Benjamin Mayo:

Most of the privacy dialogs in Catalina are sane; patching holes in the permissions system that should have been there for years already. Nevertheless, Apple could have come up with a better policy where you don’t get bombarded with dialogs from every app all at once.

Jeff Johnson:

A good practical joke to play on someone running Catalina:

$ tccutil reset All

Mr. Macintosh:

This article will show you how to Manage Catalina’s New Application Notification Preferences with a Config Profile.

Craig Hockenberry:

If you think the Catalina permissions problem is bad from a customer’s point-of-view, it’s absolutely brutal for developers.

The security prompts are so half-baked that developers have to guess about permissions. And since we don’t know the internals, that guess can be wrong.

Rui Aureliano:

Dear macOS developers, recently for Catalina we see this window for Screen Recording permission. Has anyone found a way to check if it’s already granted?

Matthias Gansrigler:

this is how I do it in @ScreenFloatApp.


Tyler Hall (Hacker News):

But Catalina has been different in two particularly gruesome ways that get even worse when combined.


I’ll go through some of the highlights (lowlights?) I’ve run into below, but I guess this is my thesis: The final (well, first) Catalina release along with the outright awful public beta makes me think one thing. And that is Apple’s insistence on their annual, big-splash release cycle is fundamentally breaking engineering. I know I’m not privy to their internal decision making and that software features that depend on hardware releases and vice-versa are planned and timed years (if not half-decades) in advance, but I can think of no other explanation than that Marketing alone is purely in charge of when things ship. Why else would stuff so completely broken and lacking the attention to detail that Apple is known for and (ahem) markets themselves on have shipped if not than to meet an arbitrary deadline? Apple has so many balls in the air – and this metaphor doesn’t really make any sense now that I’m typing it – but they’re all interconnected now that Apple is a services company. And as a services company they must find a way to ship features, fixes, and updates outside of the run-up to the holiday season.


After upgrading to Catalina, macOS made me reauthorize every app that wanted to send me notifications. Ironically, the following alert appears every time I reboot despite always dismissing it using the most definitive option Apple provides and never giving whatever-process-is-showing-it permission to notify me of anything in the first place[…]

Thomas Claburn:

Since at least 2015, developers and other technically-savvy folk have fretted that Apple’s software quality isn’t what it could be. The gripes reached Apple executives and by 2018, there were reports that company technical leaders were focused on improving quality.

To judge by the reception of macOS Catalina, aka macOS 10.15, it appears Apple’s quality push was more aspirational than actual.


Things are so broken here at Apple. I joined about 4 years ago.

I am awed by the fact that we manage to release any software at all, let alone functional software.

The biggest problem is communication. No one fucking communicates.

- No communication between orgs. Tons of bureaucratic tape to cut through just to get a hand on someone working on a different product

- Barely any communication between teams. Literally every group of 4 people is in a little silo with no incentive to go outside it

- Broken management structure. I have had many managers (a red flag in itself) but even worse none of the managers take suggestions from engineers. Everything is purely top down. If an engineer realizes there is a problem on a macro scale they cannot fix it. It is literally impossible to unite more than 1.5 teams to get anything done.


- Culture of secrecy means nothing gets fucking done. You file a bug report and you can’t even see it any more for some orgs


When I worked there under SJ, the Mac OS org (then under Betrand Serlet), it was sort of open amongst the org itself. It was really easy to walk to someone’s office and strike up an interesting conversation. Many late nights were spent working through collaborative problems. Or randomly, I had a friend who would pop by my office and spend hours explaining how he figured out some complex Javascript compiler bug of the day.

It always felt like we were in a mission to ship Mac OS together. What Apple did do back then was create these special versions of the OS that had a few key hidden/secret products that SJ was going to demo, like iTunes or iPhoto. So while I could install the latest internal developer build of the OS, it would have a feature or two missing. You would then get radars that mentioned the code-name and explained a bug that you had to fix for the feature, but you had to fix the bug blinded and send the bug back to verify. (Radars could never be closed until the original creator verified them) The secrecy didn’t really get in the way and it made for an interesting culture.

Then it all started to change when Forstall was promoted to VP of the iPhone effort. He took what was probably meant to be a short term secret launch team culture and expanded it to create this massive secret island in the company. The program office and by extension, the original founding engineers were all promoted to management that expanded on the secret culture. I think if management meant to open the culture back up to the same level as Mac OS in 2009, they would have been burned by Samsung and Palm WebOS making exact copies of the software coming out at the time. So the hyper locked down culture persisted and SJ passed away. Then Forstall was fired and Federighi was promoted to replace him and merge both the Mac OS and iOS orgs finally killing off any of the remaining openness that once existed.

Then came all the ridiculous tools such as checking someone’s security clearance when you had a meeting with them.


I should note that most developers here really do care, and that’s probably why products can be released in the first place. You have to have really dedicated people willing to cut through the organizational bullshit to get things done.

All of the engineers I’ve met here are smart and innovative. Only if we could organize, things would be much better.


Tyler Hall (Hacker News):

I fully stand behind every criticism I leveled at Apple. From the specific bugs, to the broader statements about detecting a lack of focus on the Mac in recent years, to my final thesis about their lock-step, annual release cycle hurting the company’s ability to maintain software quality.

But the part that wasn’t fair. The parts that I regret are my direct insults at those in charge.


Around 11am the next day, I received a Twitter DM from an Apple engineering manager who (I thought) had somehow stumbled across my post. And they very kindly asked if I could jump on a call to go into more details about my post and the bugs I identified. They were super awesome and I’m looking forward to working with them more this week.

They say that running to the press “never helps,” but the Mail bug that’s causing users to lose hundreds of thousands of e-mails was reported months ago via a bug report that was apparently ignored. Hall’s concerns are at least being heard.

Luc Vandal:

Really Apple, why bother with this yearly update cycle non-sense if it just adds more bugs that are annoying your users and prevents them to actually do some work? We need stable OSes, not full of bugs shipped because of some marketing-force deadline.


And I’m not blaming Apple engineers, which are doing their best. I think the issue is within high management.

Michael Rockwell:

Apple should just take the next year or two and Snow Leopard every piece of software they make. Fixing bugs and improving overall quality needs to be their number one priority.


The position of Apple today reminds me a lot of Microsoft after they peaked (~2000?). Cocky to the point of arrogance because of market position, past innovations and brand loyalty (e.g., it is cool to own Apple). But loyalty and market sentiment can only endure so much amidst plummeting product quality, nonsensical pricing (e.g. dongles) and lack of any meaningful innovation (thinner doesn’t count). Apple doesn’t listen because they think they know better (and that used to be true).

These seem to be common sentiments, though I don’t understand the persistent claim that Apple hasn’t innovated lately.

Justin Blanton:

I genuinely can’t remember the last time I was even remotely excited about macOS/OS X. All I really care about these days is that the newest version doesn’t break shit. 🤷🏻‍♂️

Jeff Johnson:

Let’s not forget that Apple used to charge $129 for Mac OS X updates.

If they charged $129 for Catalina, it would be DOA.

John Gruber:

That’s an interesting measuring stick. A MacOS update (or iOS for that matter) should feel like something many users would pay for. If it doesn’t that’s a problem.

Joe Rossignol:

Apple shares are currently trading above the $234 mark on the intraday market, setting a new all-time high for the company.


Update (2019-10-17): scott:

The selling point of Catalina is it will be the only version of macOS that runs on Macbooks with scissor switch keyboards.

Update (2019-10-21): David Shayer:

In a well-run project, features that are lagging behind are cut early, so engineers can devote their time to polishing the features that will actually ship. But sometimes managers play “schedule chicken” since no one wants to admit in the departmental meeting that their part of the project is behind. […] Apple could address this scheduling problem by not packing so many features into each release, but that’s just not the company culture.


When I worked on Apple products, we’d get a list of the top bugs driving Apple Store visits and support calls, and we were expected to fix them. […] Unfortunately, bugs that are rare or not terribly serious—those that cause mere confusion instead of data loss—are continually pushed to the back burner by the triage system.


But if you file a bug report, and the QA engineer determines that bug also exists in previous releases of the software, it’s marked “not a regression.” By definition, it’s not a new bug, it’s an old bug. Chances are, no one will ever be assigned to fix it.


No need to go into the details here, except to say that, apart from a few specific areas, Apple doesn’t do a lot of automated testing. Apple is highly reliant on manual testing, probably too much so.

Riccardo Mori:

What I want from a new version of an operating system, especially one as mature as Mac OS, is that it fixes or improves what was not working well in previous versions, and that it leaves tried-and-true features and functionalities as untouched as technically possible. I don’t need and I don’t want disruption for disruption’s sake on a yearly basis.

Update (2019-10-22): See also: Hacker News:

Colin Cornaby:

I feel like Apple needs to take an OS release cycle just to fix their internal process.

I know it’s a political problem and not a technical one that can’t just be solved by throwing a unit of time at it. But still. Makes it harder to fix actual bugs.

The repeated whispers of a lack of automated testing is concerning just because it’s so hard to ensure quality at the scale Apple is trying to ship at. Either you hire a lot of QA engineers (which Apple doesn’t seem to be doing) or you automate the heck out of things.

The challenge is that it’s a political problem and they need to throw a unit of time at it, which is also a political problem.

Update (2019-10-23): See also: Hacker News, John Gruber.

Bob Burrough:

I worked with David, and I have great respect for him. However, the premise is false. iOS 13 and Catalina are not any more bug-riddled than any release over the last five years. They’ve all been filled with bugs.

Dave Mark:

This one passes the vast majority of those tests. This doesn’t feel like post-Apple spite, but rather a knowledgable take on problems, with thoughts on where things are going wrong.

Apple is a fast moving train, steadily producing and refining immensely complex products. Apple is dancing to the opposing forces of satisfying shareholder demands for ever-increasing growth, and user demands to stop and fix the bugs. Short of halting forward progress and retooling, there’s no easy answer here.

Peter Steinberger:

I still remember at WWDC a few years back, I went with some older radars to the labs, only to get turned down with a „You already have a workaround - why do you care?“

...that made me mostly stop filing radars for older issues. (There are just too many, not even mad, mgmt issue)

Jeff Johnson:

If Apple’s reputation is temporarily dinged, but that doesn’t hurt the company financially, does it really matter to current leadership?

They’re still better than the (sucky) competition. It’s a can’t-lose situation.


Apple is in a comfortable, stable duopoly with Microsoft on desktop and Google on mobile.


The awful truth of the tech industry is that technical debt is profitable. It doesn’t pay to fix your bugs. You have to do it because you care, not because your stockholders care.

Andrew Hoos:

If you know anyone that wants to be a part of expanding automated testing at Apple. We are hiring: backend (Scala), client (Python, Objective-C, Swift), infrastructure (Kubernetes), and frontend (some kind of js I guess).

Update (2019-11-06): Manton Reece:

Day 2 of Catalina, now hitting more issues with full disk access and Ruby-related commands. Using rbenv and starting to wonder if I need to throw everything out and re-install to make Catalina happy. I’ve added all the obvious paths to System Prefs.

Rui Carmo:

Apple’s software QA has become so much of a risk to my personal productivity that I’m (again) considering switching to a Linux desktop, and only a combination of inertia, real life and my working at Microsoft has prevented that from happening.

Update (2019-11-27): Maxime Chevalier-Boisvert:

I decided that today I was finally going to upgrade MacOS after putting it off for a year. Three hours later I’m still trying to get my MacBook Air in some kind of working condition. :'(


As far as I can tell, the OSX installer corrupted my filesystem while trying to convert it to APFS, and left it in a broken state.


"I want to make clear that I’m not blaming the talented Apple engineers who obviously worked their butts off on Catalina just like they do every release."

This is a bit worrying if they really worked their butts off to produce this OS release…

@someone It seems totally plausible that there’s too much work to go around (how many operating systems now, plus technical debt?) and that they are working hard but not necessarily on the things we (or they) want. Plus the structural and communication impediments that have been mentioned.

Can verify that the assessment of the software org's dysfunction (Apple as a whole to a lesser degree) is more accurate than not.

>This is a bit worrying if they really worked their butts off to produce this OS release…

There's no doubt that they did. In fact, working in an apparently completely dysfunctional oranization just creates additional work and stress. Also, a yearly update schedule is brutal, particularly if you work on something that needs to ship in a new version with every release. You have no downtime to consolidate and refactor stuff, you go from cleaning up the mess from the last release straight to planning and executing the next one.

On a personal note, I just sold my last 2013 15" MacBook Pro, and I now have only my trusty old 17" MacBook Pro, and my work Mac. My 17" can't be updated to Catalina, and my work Mac isn't allowed to, so there's a good chance that I'll never run Catalina on anything. Good job, Apple!

Sören Nils Kuklau

Some of this seems unavoidable, and some overblown. But some does seem self-inflicted.

There were many problems with both the development of Windows Vista (which at one point became so Copland-esque it needed a “reset” where a wild amount of features was killed off, some of which — sadly! — Microsoft still hasn’t tried again to ship) and its release.

From a user point of view, I get that UAC permission dialogs were particularly unpopular. I also get that it was, frankly, an easy target for Apple’s marketing (and at the time, the evolution of Mac OS X felt so much more nimble than that of Windows). But Microsoft wasn’t wrong to ship UAC, and Apple isn’t wrong to do the dialogs. So I think the “forgetting their own credo” quip in particular (and therefore, apparently, Apple’s own Keynote slide!) is misguided.

While different in some details, UAC is really quite similar to the sudo/Authorization UI pervasive since Mac OS X 10.0, where, even if you’re technically an admin (but especially if you’re not), giving processes temporary access to root requires consent. (And literally, Windows’s UAC UI is in a process called consent.exe.) Microsoft made the same observation Apple a few years earlier: that if requiring admin access to perform some tasks is too cumbersome, people will simply give themselves permanent admin access for all tasks. Windows XP had a notion of non-admin users, but nobody wanted to live their lives that way.

The pattern isn’t that security UI doesn’t work. It’s that excessive security UI does not work. That leads to users getting Pavlov-trained to read dialogs even less and click whatever button looks positive even more quickly. And UAC in Vista was excessive. Boy, was it. As I recall, you needed admin permissions to change the screen resolution.

So while introducing UAC was correct and a prudent countermeasure to a perception (and reality) of increasing security issues in Windows, they went too far in one direction. They toned it down significantly in 7, but the damage had been done. And it seemed unnecessary. Vista had literally years of previews (some of them semi-public), so they had an abundance of time to collect feedback.

Apple’s approach, to their credit, has been more gradual. SIP was introduced in 10.11 (?), and some of the permission dialogs, such as those asking access to your Contacts, have also been around for a while. But with 10.15 Catalina, for reasons not clear to me and apparently not communicated to anyone, they made one big step. Possibly too far, and arguably quite abruptly.

Unlike with Vista, macOS these days has just about four months for semi-public feedback. This is largely a self-inflicted wound, and the perception of poor design decisions (like this one) and poor quality seems like an unforced error.

These seem to be common sentiments, though I don’t understand the persistent claim that Apple hasn’t innovated lately.

Justin Blanton:

I genuinely can’t remember the last time I was even remotely excited about macOS/OS X.

I agree with both of these sentiments. Not sure how you would even begin to objectively measure innovation, but for some of their stuff, the level of iteration seems fine to me.

Ironically, we might actually think more highly of it if they didn’t churn out updated every year. How about a tick-tock cycle? New iOS, watchOS, tvOS, whatever stuff in 2020, then new macOS stuff in 2021. Give each major release 24 months to mature. (One flaw in this approach can be seen when looking at something like Reminders in iOS 13 / macOS 10.15: sometimes, apps are coupled to multiple OSes and their online iCloud service, and then a staggered roll-out becomes near-impossible to do.)

macOS 10.15 Catalina isn’t exciting, I would argue, for multiple reasons:

the years of early Mac OS X where so much was missing are long over. < 10.1 lacked disc burning and DVD playback, < 10.4 system-wide search, and < 10.5 an official backup solution. Compared to those, the feature set of 10.14 and 10.15 seems quite quaint. Not much Apple can do here. That’s kind of a good thing.
apps have been moving to the web. Apple needs to fight harder to make the case that non-web apps are great (which I continue to believe!), such as for privacy reasons. If they don’t, the question increasingly becomes: why would I use this over a Chromebook?
it cuts off 32-bit support. I support them in doing so, but they didn’t have to, and they also didn’t have to approach it the way they did. For example, Windows 7 shipped an “XP Mode”, which was an entire VM (based on Connectix Virtual PC) with Windows XP in it. Apple could’ve used their own Hypervisor framework to build a 10.14-in-a-box. Or wrapped a VirtualBox. Or cut a deal with Parallels or VMware. Or just provided support document pointers on how people can do this themselves. They chose to do nothing and leave people out in the cold.
the interval between releases has shrunk. That’s entirely on Apple.

But perhaps mostly: they… don’t seem to care as much. I remember getting excited when there was an “iWork” and it had Keynote, which was a great contender against PowerPoint at the time (these days, PowerPoint has mostly caught up). And it had Numbers, which had a refreshing approach to laying out a spreadsheet (Excel still has the fundamentally problematic worksheet approach). And Pages! They… somehow made an office suite cool again in the 2000s. But in 2019, none of that is cool any more, and they don’t seem to care. They don’t even demo it. They just update it now and then, and then let it linger again. There doesn’t seem to be an advocate (or the desire to have an advocate) for these apps. Does someone at Apple love apps like Garage Band, iMovie, and Clips? (Does someone at Apple remember they exist?) Show us!

Meanwhile, we got Microsoft trying to get people excited over… a new Terminal. Apple’s heart isn’t in that, and Microsoft’s is.

It’s interesting, actually. I’ve had far worse macOS upgrades, but decided to upgrade when the GM seed came out. I’ve run into one app that was 32-bit, but found an update. corespotlightd gobbles up too much RAM (reported as FB7347113), but other than that, about two weeks in, it’s actually been smooth sailing for me.

But it also hasn’t been exciting. The Mac is too old for Sidecar. The Watch is too old for unlocking apps. The Mac is probably too weak for gaming, but I haven’t really tried (Arcade might be fun on it?). Regarding Catalyst, I’m happy Home is available on the Mac (since Mojave… unfortunately, Health still isn’t), but its UI is laughably bad for a platform once considered the benchmark of good UI.

Sören Nils Kuklau

This is a bit worrying if they really worked their butts off to produce this OS release…

To be fair, there has been behind-the-scenes stuff that users won’t immediately benefit from, like gradually phasing out kernel extensions in favor of higher-level, more specific APIs. Ars Technica went into some detail.

too much work to go around (how many operating systems now, plus technical debt?)

Yup. Which is why they want to share more and more code between macOS and the iOS-derived OSes (tvOS, audioOS, iPadOS, … how much am I forgetting?). Which in turn is why they’re cutting off stuff like 32-bit.

It makes sense, but like infamously with discoveryd, the bumpy road there seems never-ending, and they don’t seem very empathetic about what the interim means for some users.

>Apple should just take the next year or two and Snow Leopard every piece of software they make.

Yes, I agree wholeheartedly, but I'm not sure if they're capable of this anymore.

If anything, Catalina should have been the new Snow Leopard, given how the removal of 32-bit/Carbon is a substantial streamlining on par with 10.6's removal of PowerPC support, if not moreso. Part of the reasoning behind getting rid of 32-bit was to reduce complexity/tech-debt/maintenance burden, right? Yet, reliability and functionality are worse than ever (or at least in the 15 years I've been on the platform, since 10.3).

Much like Lukas, I find myself without a compelling reason to ever upgrade to Catalina. If this is the future of macOS — and apparently it will be unless management practices change — I then I have to admit I can no longer rely on it for getting stuff done.

It's annoying, but the way I see it is I have two years (of Mojave security updates) to figure out where to go from here. I'd rather not, because I have a substantial investment in muscle memory as well as 3rd party apps, but I don't see much choice if Apple keep shipping an unreliable operating system. I mean, frustration with an unreliable operating system is why I switched away from Windows XP to begin with! That's why this situation is so ironic.

>I don’t understand the persistent claim that Apple hasn’t innovated lately

Perhaps it's a matter of context, i.e. who does Apple innovate for nowadays? Expensive smart watches, expensive smartphones with impressive internal hardware, music streaming, original TV shows and entertainment... those are all well and good, but of no interest to me. So even if Apple are still innovating, it's in areas that are irrelevant to refining — or even maintaining — personal computers 'for the rest of us'. I feel like it's that loss of focus that's behind a lot of hand-wringing among indies and geeks like us.

For me, the last time Apple made a new Mac that suited my needs was 2010 (the tower Mac Pro)... at least that model was priced such that I could afford a used one 5 years after its release. No such hope with the upcoming tower, and all other Macs are either underpowered, come with glossy screens, or are not user-upgradable. At some point I have to realize that Apple are no longer interested in manufacturing work trucks.

All I can say is that I find it unbelievable that Apple can spend $6B on some spaceship campus, but obviously didn't put anything into improving QA. Even a few 10's of $million would hire/train more than a few people that could help identify & improve all the bugs.

I personally know and have worked with people that have been/are at Apple, so I know that the engineering crew is smart, capable and dedicated people. But clearly, the management at Apple has gone off the fucking rails. I guess that's "courage" for you.

Kirk McElhearn

I’m still irked that they took away the column browser from the Music app. It was the most efficient was to browse a large media library and had been in iTunes since 1.0. An Apple source told me that it wasn’t widely used, but those who did use it are stuck with clunky navigation and music selection options.

Whoa! Seriously? When I had iTunes, I used the column browser all the time. That's a shame.

"Holy, what an incredible post batman!"

In all seriousness, I think you bring up a lot of good points. Let me focus on one, the idea Microsoft is courting the hardcore tech crowd with recent versions of Windows. Yes, yes they are, aggressively. If I refused to run Linux directly because it was too hard for day to day use (not my personal thought, but I respect that opinion), I would not hesitate to suggest Windows. If you need Linux tools, the subsystems can be installed directly from the Windows App Store!!!! Now contrast with the worthless Mac app store and Apple pulling out as many command line tools as they can from the base system.

[…] Catalina Vista on Michael Tsai’s blog makes me sad. I more importantly feel for all of the very talented Apple engineers who are suffering through a systematic failure of management to address issues, innovate and drive the desktop OS. “No new features” for the next 3-4 years of MacOS would make me so happy. More: […]

Stay up-to-date by subscribing to the Comments RSS Feed for this post.

Leave a Comment