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Mail Data Loss in macOS 10.15 (mjtsai.com)
280 points by zdw on Oct 11, 2019 | hide | past | favorite | 128 comments



I always find it strange when OS updates affect apps in this way. It just shouldn't happen. It reminds me of when Linus preaches that "the kernel should never break userspace". Why would a OS update suddenly cause the Mail app -- developed by the same company as the OS, for what it's worth -- to have these strange (and catastrophic) data syncing issues?

And, just to add, I am tired of OS updates updating and/or releasing userspace things like "Music" and saying:

> iTunes forever changed the way people experienced music, movies, TV shows, and podcasts. It all changes again with three all-new, dedicated apps — Apple Music, Apple TV, and Apple Podcasts — each designed from the ground up to be the best way to enjoy entertainment on your Mac. [0]

It is literally the FIRST thing they advertise. What does that have to do with the OS? Nothing! They should release apps separately from major OS versions.

[0] https://www.apple.com/macos/catalina/


The new OS comes with new versions of apps, and that's usually fine because they're either fixed bugs or added features; the main problem is Apple's internal culture that seems to be preaching "change is good, constant change is always good" --- as I explained in this comment I made a few days ago, the love of constant massive internal changes to their code always tends to cause such bugs:

https://news.ycombinator.com/item?id=21174947


It makes sense now because they said bug is a feature. No surprise.


>I always find it strange when OS updates affect apps in this way. It just shouldn't happen. It reminds me of when Linus preaches that "the kernel should never break userspace". Why would a OS update suddenly cause the Mail app -- developed by the same company as the OS, for what it's worth -- to have these strange (and catastrophic) data syncing issues?

It's doesn't "suddenly" cause the existing Mail app to break.

It's the new version of the Mail app that breaks -- for reasons not having to do with the rest of the OS.

macOS, as an OS, is not just the kernel, SDK, and GUI libs, and tooling: it's rather a distro that includes regular apps like Mail, Safari, Notes, etc.

If it was OS caused, it would affect others apps too.


Because to Apple and Microsoft, the OS is the experience, not just the kernel and some runtime bits of userland. It's more accurate to compare a macOS release to a new Ubuntu release (which updates a bunch of apps in the process), but still not entirely so since they don't insist on tying the default apps so deeply into the OS innards as Apple and Microsoft do.


> I always find it strange when OS updates affect apps in this way. It just shouldn't happen.

Right? Are there not automated tests for this stuff? I would expect that if you commit something that causes this, the next day you get an email that says, "your name is on commit $FOO, which caused regression tests to fail in tests/firstparty/apps/mail; please fix it (sincerely, Jenkins)" or so. Heck, it's more egregious here because it's a first party application, but it seems like it would be in their interest to keep copies of the most popular third-party applications and include those in their test suites as well. ("Hi, Adobe? Hey, it's Apple. Hey, so this is a heads up that Photoshop doesn't work with the new OS version; we're sending you a RCA so you can fix it before it hits end users.")


I wouldn't place much emphasis on testing, and Apple most likely has tests, because the exact conditions that trigger such bugs are often so narrow that an artificial testing environment for them to "make the stars line up" would be nearly impossible to create. Anything involving multithreading/asynchronous code tends to fall in that category, but even single-threaded code can be like that; to make an artificial relevant example, it could be something like "if two consecutively received emails are exactly 8192 bytes long[1], and the first one is the 256th message in the folder when sorted by the sender's email, then the second one will be missing." That's a condition which you're highly unlikely to hit, even more so if you're generating test data randomly (as some tools like to do, and fuzzing is one prominent example). Even if you specifically test power-of-2 sizes, the two-in-a-row subcondition would make that improbable. If you let everyone in Apple "dogfood" the software, they might not hit. Yet everyone who has subscribed to a set of mailing lists that happened to issue such an exact sequence of messages would see the bug.

That's also why I think other automated tools and "code quality" metrics don't help so much; tests are more of a sanity/last-chance check and shouldn't be relied upon to catch everything. Correctness should be assured through design and code reviews, and for that nothing beats the power of intense mental deliberation. To paraphrase a popular saying, "there is no replacement for intelligence."

[1] https://news.ycombinator.com/item?id=8797640


You are absolutely right, but all of this is known to Apple.

What they need to do when it's potentially about permanent loss of user data is to prove that a postcondition is met (i.e. all messages were successfully converted) and roll back if it isn't.

Instead they apparently sync the faulty data with the IMAP server and destroy what most users consider their email backup. This is breathtaking incompetence and negligence if it's actually true.

The worst thing is that it is near impossible to find out whether or not you're affected by this.

I'm so fed up with Apple and its second rate software. I have lost music playlists in this ill fated Catalina "upgrade" as well. I've been wanting to move on to a more flexible and less oppressive environment for a while. At least this finally breaks my inertia.


>I'm so fed up with Apple and its second rate software. I have lost music playlists in this ill fated Catalina "upgrade" as well. I've been wanting to move on to a more flexible and less oppressive environment for a while. At least this finally breaks my inertia.

Try Linux or Windows! Their first rate apps will keep your email safe and secure!

https://bugs.launchpad.net/ubuntu/+source/evolution/+bug/372...

https://forums.linuxmint.com/viewtopic.php?t=88648

https://blog.lightlyseared.online/2010/04/06/fixing-corrupt-...

https://windowsreport.com/outlook-emails-disappeared/

https://thenextweb.com/microsoft/2013/06/20/outlook-coms-mis...

https://www.pcworld.com/article/237103/five_outlook_nightmar...


You're missing the point. If I'm getting shoddy QA anyway, why keep paying Apple's excessive prices and accept their oppressive content restrictions?


No reason, especially since others are both cheaper AND better at shoddy QA!


>Right? Are there not automated tests for this stuff? I would expect that if you commit something that causes this, the next day you get an email that says, "your name is on commit $FOO, which caused regression tests to fail in tests/firstparty/apps/mail; please fix it (sincerely, Jenkins)" or so.

Do you really believe they aren't running automated tests at Apple?

It's more likely than not, that this was not caught by one of the tests...


You have a very outdated vision of what constitutes an OS. (Or perhaps a very Linux-centric vision.) Nowadays an OS is far more than just a kernel. It's the associated userland libraries, frameworks, and basic utilities. And yes, the scope of these basic utilities have expanded far beyond just shell-utilities like sh or cat; they now include things like a graphical mail client.


How is that a Linux-centric vision? Linux distributions have always tightly coupled application updates to OS (distribution) updates. In fact, this was often a criticism of Linux and one of the motivators for a lean immutable system like Fedora Silverblue, where you install and update applications out-of-band with Flatpak.


>How is that a Linux-centric vision?

In that many people consider the Linux kernel and basic userland as the "OS", and the applications, packaging, etc as the "distro".

Even casually, when we mention OSes, we say "Windows, macOS, Linux", not "Windows, macOS, Ubuntu, Debian, Centos, etc etc...".


I'm talking about the Linux project. You're talking about GNU/Linux distributions.


I’ve always seen MacOS releases like a UNIX distribution release, encompassing more than just the OS, including userland applications and development tools.

It seems that by locking their userland application release cadences to that of the rest of the distribution they lower the number of unique configurations of userland applications and OS components they have to support in the wild. I’d imagine this has implications with regards to the cost of support.


This happens to iOS: every time there's a new major version coming, the layout of many apps breaks for some reason and elements move all over the place. I wonder why.


Huh? Never happened to me, much less "every time".

I had some apps break and need update after an iOS update, but not layout problems in apps... at least not in the 50+ non-Apple apps I use...


WhatsApp currently has some weird layout bugs when swiping back to the root view for me.

More annoyingly, it seems the changes to how multiple windows are handled has made it so any visible notification will prevent me from interacting with anything except the notification, so I can't ignore them anymore - I have to dismiss them to carry on using the phone.


I see. Don't use WhatsApp anymore, so can't check.


Well "otool -L iTunes" shows Carbon in there, and Catalina doesn't have Carbon.


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).

- Peaked in terms of brand perception rather than market cap or market share.


The Mail app in Leopard had a bug that would spam recipients with copies of drafts as they were typed and saved automatically by the app.

Not an apologist, but showstopper bugs were a thing even under Jobs.


Yeah, I hit a bug where it deleted my contacts and then synced the deletions across devices. :(


I ran into the same problem but was able to fix it with Time Machine. The contacts app has special support for Time Machine (you can slide through time and don't have to go to the Finder) and I could restore all my contacts from a few weeks ago.


It wasn't obvious at the time, but I think in retrospect the case can be made that Apple's ability to innovate effectively (both in terms of time and quality) died with Jobs.

Jony Ive made a good effort to keep pushing hardware design forward, but without Jobs to curb his worst impulses (in my opinion), the end was result was "thinner above all else" (as you mention).

If someone can come up with a corporate structure that allows for the dynamism provided by having a visionary dictator at the helm, without actually needing a visionary dictator, that would be a corporate structure that would take the world by storm.


>> structure >> dynamism

Almost antonyms, which is perhaps why it's so hard to do without that visionary leader. A philosopher king if you will. Or benevolent dictator for life.


> It wasn't obvious at the time, but I think in retrospect the case can be made that Apple's ability to innovate effectively (both in terms of time and quality) died with Jobs.

Oh stop. Apple's effectiveness was entirely a product of its time. You had designers building the Zune and calling it competitive but really there was no competition for the products Apple was building for a market that was screaming for a better balance of form vs function.

This picture of Apple's innovation includes no part of OSX, which was always an OS that was technically capable but superbly messy and extremely behind on the times.

Innovate effectively? For a long time of Jobs' tenure, Cocoa was being supported on BOTH Objective-C and Java, and when they ripped it out, they actually chose Objective-C, not Java, as their platform of choice (in retrospect: wow), only to have to build yet another platform (Swift) just a few years later (Swift of course, based off of MacRuby, which they initially tried to build Cocoa on top of internally, so I hear).

Innovate maybe, but effectively no. There is a whole host of broken, abandoned, and outright bad decisionmaking in the OS layer at Apple. Apple's success has everything to do with their success with industrial design, UX design & marketing, and just a bit of being at the right place at the right time.

IMO this interpretation fits the timeline much more cleanly: Apple was churning out the same iPhones and Macbooks long before Jobs left, just as they had been before with the iPod. The butterfly switches, the thin above all else, that's all part of Apple's MO dating back years. Lack of FM radio on the iPods, lack of IR sensors on their early phones, removal of removable batteries, headphone jacks, USB-A, etc, is all part of the DNA. A $5000 screen is not surprising to anyone who saw the Powermacs of the last generation. Butterfly switches look an awful lot like bendy iPhones, which look an awful lot like DOA Powerbooks.

I'm really not sure what part of this is new post-Jobs, but I have a good feeling this is a great case study of confirmation bias. If you believe Jobs was a one-of-a-kind irreplaceable visionary who was single handedly responsible for Apple's success, then you have no choice but to interpret any action Apple makes post-visionary as a failure, otherwise you were wrong about the one-of-a-kind irreplaceable visionary.

And it would be a pretty big blow to most to be wrong about Steve Jobs.

The other interpretation, of course, is that Jobs was not a magical visionary, just a smart guy who made a couple of right decisions, got lucky on lots of others, while still getting it wrong on plenty of occasionss (Macintosh TV cough Apple TV cough Apple TV2), just like most fallible humans.


Apple only kept Java around because coming from Pascal and C++ background they were unsure how the Apple developer community would welcome Objective-C.

When they saw the community had no issue embracing Objective-C that is when they dropped the Java bridge, QT for Java and eventually their own JVM.

Chris Lattner never speaks about MacRuby on his interviews, rather how, like clang before it, Swift started as a side project before being shown to upper management.

According to his interviews, many of the Objective-C 2.0 and later improvements were already a kind of slow roadmap into Swift.


Yeah, but Objective-C 3.0 would have been a much better path than Swift. It would have allowed easier upgrading to existing code instead of mass rewrites, which always bring their own bugs (and that's ignoring the bugs in Swift itself).


I don't know if I'd term it 'cocky'. It's more that they don't have to pay attention to the competition so their mind wanders. When you're behind you can have laser focus on precisely what's important and what's not. MacOS isn't important to Apple any more which is why they have an OS full of bugs.


What's thin at Apple? They aren't the thinest by a long shot now a days. They aren't the lightest. They aren't the most powerful. There was a time when a Macbook Air was kind of thin and light compared to other laptops. Now it's neither by comparison to the competition. Plenty of thinner lighter more powerful laptops. iPhone nor iPad is also not even remotely the thinest. There was also a time when a Macbook Pro was a top end laptop. That's long not been the case, in particular the underpowered GPU. I own them all but am tired of waiting for Apple to lead again.


I don't get the downvotes. I'm an Apple fan. Apple pushed the crap out of the Air when it came out as the lightest thinest laptop. It's not anymore. Not even close. I want Apple to reclaim the throne. What is there to downvote?

Similarly 2008-2012 or so AFAIK, maybe I'm mis-informed, Macoobk Pro's were top of the line notbooks, no compomises. I've from now through then and am typing on one now. But, now they aren't the top. Low powered GPU means all my graphics friends have had to switch. Some of them had previously bought Macbook Pros and installed Windows but they can't even do that now as the GPUs just aren't there. eGPUS don't count as they aren't portable by any reasonable defintion of portable. I want Apple to reclaim the throne here too. What's is there to downvote about that?


A lot of this is a repeat of weird issues that we saw 8(!) years ago with OSX Lion. Perhaps I'm off the mark here, but I strongly suspect there's lack of a proper manual QA team at Apple.

QA at most so-called "modern" companies these days has turned into overly fetishising automated testing. Automation is valuable, but crucially also leads to situations where the least-common-denominator situations get tested since it's easier to automate the conditions for testing them. So for example you might write an automated test that verifies that the mail index is correctly upgraded from (say) El Capitan to Mojave to Catalina; but that doesn't show the whole picture. There could be 20 other complex factors that affect it when it's used as part of an OS upgrade, and none of those get tested.

Project managers, line managers, and other suits also seem to love automated testing, because you can show off some kind of real number to someone in an "Oh we wrote 200 tests this cycle, isn't it great that we can run them everyday" way, even if there are 0 issues found. Manual testing in the same case leaves you with no output that can be run in an automated fashion. Also, no one wants to argue against automation (even if it's taking away manual testing resources) because that can make you seem old-school and out of touch. And once this attitude gains steam, no one on the QA team will want to go against the grain and say "You know what, we should spend more time not writing automated tests".

All of this is to say -- sometimes during testing, you simply have to put yourself in a user's place (for as many different kinds of user you can imagine) and actually use the thing you're supposed to be testing. I strongly suspect that Apple is not investing enough, or at all in this kind of testing. Instead, they are pushing it off to those enthusiasts who install and use beta or newly released versions of their software. So far, this strategy seems to have paid off for them, but perhaps people will wise up and stop testing their stuff for free. I am certainly not upgrading my machines to Catalina any time soon.


Also, no one wants to argue against automation (even if it's taking away manual testing resources) because that can make you seem old-school and out of touch.

As someone who is "old-school" and has argued against automation countless times, it's more that your arguments against it will likely be dismissed because the management just wants to see the numbers on their pretty "quality metrics" dashboards going up; regardless of what it means for the actual quality of the product. They'll even ask you to "fix" automated tests by forcing them to pass, if they are failing for some reason you don't know yet. Truly a case of "you get what you measure". It's only when you start showing them the bugs that customers come back with and why they couldn't possibly be discovered in automated testing (at least without an impossibly large and nearly-infinite set of test cases on a similarly large set of hardware and software) that they may start to listen to you. Sometimes.


When they’re ready to listen, what do you propose instead?


> lack of a proper manual QA team at Apple

Yeah, I think so.

Apple's apps have always been terrible, and it seems weird because their Mac OS (though of course buggy in absolute terms) has, for almost 20 years, far outshined any other desktop computing OS of similar complexity (meaning, basically, Windows and Ubuntu and equivalent Linux-plus-all-basic-apps type distros).

I think this is a side effect of their silo culture. App teams are tiny, often one person, and they work in permanent stealth mode. Then they finally release a developer preview, which includes the core OS plus like a hundred app releases.

Suddenly, they have thousands of beta testers: Mac developers paying Apple for the privilege. I've been one for the past 20 years or so. But we don't have time to file bugs (especially through their shitty, rude Radar system, although it's recently finally gotten... um, marginally less shitty). We spend our bug-filing time on the OS deficiencies that are fucking up our own applications.

So the OS itself gets stress tested by thousands of developers, whereas none of us really gives a shit about the app collection that will ship alongside the OS.

E.g., relevant to this issue: thousands and thousands of developers install every OS release and beat on it, but almost none of us would expose our actual email accounts to some developer preview release of Mail.app. We'd just use a different machine, or use webmail for a while while working with the new OS.

So the apps themselves actually get released with pretty minimal real user testing.


The reality is actually the opposite. They rely pretty much solely on manual QA and only in the past few years started writing unit tests, sometimes. Apple is actually quite an old school company some ways.


Not so much automated testing but too much focus on unit and shallow integrations and not enough the big picture testing.

Such as load testing, end-to-end testing, fuzzing. All of which can be automated to a large degree.


My hypothesis is that the difficulty of writing automated end-to-end tests where failure can reliably indicate actual brokenness, combined with some of the other factors I mentioned is the reason for all the focus on unit and shallow integrations that you mention.


I wish I only lost mail data in the upgrade to Catalina.

I lost 400GB of data when the installer repartitioned the hard drive and the files that were in folders in root went bye bye.

I know I'm not supposed to put stuff there, but it was a family video project I was putting together for my wife for Christmas, and she would have seen it anywhere else.

There should have at least been a notice or a warning or some kind of confirmation. But there was nothing.

Nothing in the "Relocated" folder, either.


If you can reproduce this (I suggest using a VM, they're perfect for this sort of thing), it would be great to write it up as an article and get more visibility on it, because removing files that it did not put there is a really really serious bug.

Microsoft suspended an update after reports of data loss, and was still severely chatised for doing it (explicitly deleting files it did not create without asking permission first): https://news.ycombinator.com/item?id=18189139

I'm a long-time Windows user, have put files in the roots of drives (maybe this is not such a common thing for Mac users to do, but nonetheless the OS should not assume...), and have never had any OS upgrade remove them. It would be interesting to see what, if anything, Apple will do in response.


Check /Users/Shared/Relocated\ Items/Security/


The Mojave installer just up and trashed my whole file system. No reason to believe it can’t happen again. Always backup.


Damn. Thanks for sharing. I hope you had something on a backup somewhere


Did you backup before you upgraded?


Just so I clearly understand, if I have a lot of files and directories in say /repositories or /projects and go to upgrade, there’s a chance I won’t have that any more because I mistakenly treated it like any other *nix filesystem? That’s... not disconcerting in the least.


Don't you have to disable SIP to be able to put files there?


In Mojave, I didn't. I don't recall it even asking for an administrator's password, though it was seven months ago when I created the directories.


sorry to be harsh, but you have only yourself to blame.

1. you know not to put stuff in root. you must have disabled SIP to do this? WHY?

2. ever heard of backups? it is SO easy in mac os.


Not surprising. The new Podcasts app deleted years of downloaded podcasts when I updated, including a lot that are no longer hosted on the web. For some reason the "sensible default" in the new app is to delete anything beyond the most recent ten episodes. Now I need to remember to restore from backup before it gets overwritten, heh.


> For some reason

Giving you the other side of this: Podcasts was essentially a disk-space-leak made app, if you subscribed to any podcasts that you never actually listened to (but still listened to others, and therefore regularly opened the app.) It would just pile up new unplayed episodes forever, eventually taking up tens of GBs of space, on a device that doesn't have all that much space to spare.


> It would just pile up new unplayed episodes forever

AKA exactly the desired behavior.


Humans are forgetful, sometimes it’s nice to have machines help us organize things.


'organize' != 'delete'


Option 1: Fix the leak, i.e. the download strategy.

Option 2: BURN IT ALL.

Guess which one I don't want my apps to ever do.


Doesn't excuse user data loss


He didn't say it was an excuse, though; he just provided another perspective that may explain why Apple made the new Podcasts app that way.


Why wouldn't it prompt or inform during the upgrade or before they were deleted though?


If you have 'Automatic Downloads' enabled in iTunes, which pre-downloads any new tracks you add to your Apple Music library (as opposed to streaming them), a similar thing happens if you're subscribed to any playlists that update frequently.

For example, Apple themselves have a stack of playlists for different genres that are updated on a weekly basis, so after a few months you end up with a ton of downloaded files for songs that are no longer in your library (because they've been rotated out of the playlists).

Problem is, because they're not in your library there's nothing surfaced in the UI, so there's actually no way to know that it doesn't clean up after itself until you go to investigate why you have no disk space.

No idea if this behaviour has survived the transition to Music.app, but considering it seems to just be iTunes with a fresh coat of paint, it wouldn't surprise me.


That's a piss poor excuse. Never assume; at a minimum ask! I have many podcasts saved that as the OP points out, are no longer publicly available. A few are now locked behind a paywall but many others aren't available - period.


Apple always knows better. Even if you think you know what you want, you don't, actually. Because Apple knows better.

At least with Windows, Microsoft will never intentionally delete or cause user data to disappear. Bugs have happened (the one where files in the original Documents folder after relocating to a new location would be deleted was pretty bad), but it usually results in an apology, delaying further rollout of the patch and a fix for the issue. Instead of pretending "it's best for our users, they never should've put stuff there in the first place".


Easily solved by a notification on first use after updating which asks if you want the new default.


Oof! Thanks for the warning. I care about my podcast archives and I suppose this means I should figure some alternative out. I think most podcast apps don’t bother keeping the downloads around long-term.


An update that deletes emails is "not surprising"? I respectfully disagree.


I’ve never used Mail because I’ve never felt comfortable with Apple’s apps when it comes to long term data storage. Here Mail is said to delete data. This has happened before, IIRC. Someone in this discussion has written that their old downloaded podcast episodes were deleted on upgrade. In the distant past, Apple has also broken compatibility in data formats (for its iWork apps) and left those who upgraded with almost nothing.

Apple seems to focus too much on reinventing things, as if every app team gets a new (and inexperienced) set of developers each year and they see whatever is there as bad, incomprehensible code...so they write things from scratch, introducing tons of bugs and removing backward compatibility. Look at its app history and you’ll see a lot of work just thrown away every few years, only to be replaced with crippled applications that would take long to mature but aren’t allowed to.

Mozilla Thunderbird is “boring software”, and hasn’t made huge strides in UX in the last several years, but I trust it more than I would ever trust Apple Mail.

If I want “office software”, I have LibreOffice, which has its own issues in UX, but I can trust that it won’t drop backward compatibility at the drop of a hat.

If I want a browser, there’s Firefox. Safari 13 has become just ok now (from decent) because of the new extensions system that has junked all old extensions. It’s fine for firing up an ephemeral window, and it still provides the best battery life.

I feel the days of power users on the platform are numbered. I doubt if AppleScript and Automator will survive and be around in the next two years.

Is there any Apple app on Mac that’s been great and really improved in a stable manner?


> If I want a browser, there’s Firefox. Safari 13 has become just ok now (from decent) because of the new extensions system that has junked all old extensions.

To be fair Firefox did that recently with their transition to WebExtensions too, and Chrome will soon do something similar when they move to Manifest v3. Sadly all mainstream browsers have become "move fast and break stuff", mainly in their desperate bid to keep pace with the de facto standard that is Chrome. But most of them don't have browser dev teams the size of Chrome's...


Firefox’s transition to WebExtensions has caused pain to developers and users, but there was a warning for some years about the transition. I still don’t like where the WebExtensions API support is, and Mozilla hasn’t done much for erstwhile popular extensions like Tab Mix Plus and many others. The case with Safari 13, IIRC, is that extensions have to be developed in Swift and have lesser access than before.

While I get the privacy benefits with block lists that have been/are being/will be implemented in these browsers, the overall extensions scene doesn’t look very good. Hopefully Firefox will delay or not go with everything that Manifest V3 proposes, whenever that becomes standard in Chrome.


A counter-example I can think of is iPhoto/Photos, which seems to have just gotten better and better for me. But it is tightly integrated with iCloud so if you don’t use that I could see how you consider it to be getting worse and worse.


I recall the last version of iPhoto, before it was junked, was more powerful in editing. The Photos app that replaced it was heavily crippled and still doesn’t have some features that iPhoto had.


I have earned many thumbs down on the net for saying that Apple can't write software for shit. Apple is a design company, they make nice hardware, nice really looking hardware and sometimes performing hardware. That's it, a nice hardware design company. There software is straight up garbage and has been for a long time. Just as I have always been suspicious of those whose main OS is windows and they are not writing native windows app, I'm suspicious of those who use Apple if there full time job is not developing iOS apps. I do own a used Mac mini I bought a few years ago for the solo purpose of developing iOS apps. First time I ever upgraded it after being annoyed to death, it trashed the system and I had to do a fresh reinstall.


IMO Apple usually makes good software. That’s why the Catalina release is a big deal.

If Apple made shit software this story would be background noise, but it is surprising to see a company that usually delivers relatively polished experiences do this.


Blaming "the company" for bugs in complex human-machine systems doesn't really say anything insightful, actionable or useful.

Android, Linux, Windows, macOS and iOS are all broken, just in different ways. This is the quality that can be reached for mass-market consumer products with the standard development processes.


Yeah, good point. I am quite happy with Catalina so far so I have battled through a few issues. I think people basically have no idea what it takes to deliver perfectly functioning software. Basically, you need to combine user testing, design and theorem proving. It would be just too costly even for Apple.


I have a completely opposite opinion. I love macOS, I love iOS. But I think that Apple's devices are garbage. I don't like any current Apple device. None. The only reason I'm still using iPhone and I'm still considering to buy Mac is their software. iOS is better than Android and macOS is better than Windows or Linux.

Also, I guess, they produce good design. Their products look good, that's true. Too bad, that I don't care about looks at all.


You know I thought apple’s innovation is a hype part of jobs reality distortion field.

Then I compared iPhone and android the ux and form innovations start with Apple and are borrowed by android. Same for OS X and windows, specially the gestures and form it’s flowing from Apple.


As a daily Mac user who started to use macOS (OS X) about 7-8 years ago, I find the insurmountable number of bugs of macOS Catalina alarming. Don’t get me wrong, the situation is still much, much compared to Windows or Linux[0], buy it is alarming to see the general quality of macOS software to decrease.

I personally think it’s due to Apple engineers trying to do so much; I remember being impressed by the number of new features and changes introduced this year while watching the WWDC, but it looks like Apple couldn’t keep up its own enthusiasm.

Project Catalyst was poorly executed; I was disappointed that Catalyst doesn’t default to ‘HIG-respecting’ AppKit controls that correspond well with the UIKit equivalents (so that modal form sheets in UIKit are translated into floating windows, e.g.), and the inability to mix in AppKit controls and UIKit ones into the same view hierarchy (NSColorWell or NSPopUpButton doesn’t have UIKit equivalents), e.g.

SwiftUI is great in theory, but the tooling is immature, it’s not available to write any decently complex apps with them.

The iCloud changes were reverted right before Catalina’s release; looks like the iCloud team didn’t have enough manpower to fix all the bugs until the release.

It’s concerning, as one of the premise of macOS was that it works as expected, though that now the newly introduced parts doesn’t. I’m expecting a stabilizing release for macOS 10.16 akin to the stone-stable 10.14 Mojave, but I don’t remember 10.13 High Sierra to be unstable like this one.

[0]: For Linux users who don’t agree with this: I’ve never set up a Linux desktop system with all the hardware working without doing any ‘geek’ stuff like running some shell commands. And no, the fact that Apple only allows to use macOS only on its own computers isn’t an excuse. And no, even on well supported laptops like the ThinkPad, there are a furious amount of bugs that need ‘configuring’


The company and its engineering teams are absolutely subjected to delivering too much.

I think the prior perceived quality of Apple software was propped up by a lot of people internally grinding very hard on a far smaller set of products than the company ships today. That might work when you are at 10k people, not 120k.

It’s really time for Apple to make a good faith effort to improve its software development process. Honestly it seems more like an executive leadership issue, incessant and hasty product changes come at the cost of stability.


I am strongly of the opinion that the fixed yearly release cycle is almost unequivocally bad for macOS (and most years it ain't so great for iOS either -- 13 is still a mess).

My Mac is, and has been for many years, a 100% work machine. 'Leisure' computing for me is done on my phone or iPad, and I think the same likely applies for a lot of Mac users.

The yearly cycle mostly makes sense for iOS because they want flashy new features to go with their flashy new hardware, but the Mac has basically no schedule for hardware updates. Even when they happen, they're usually spec bumps and not the sort of update that requires new user-facing OS features.

Of course I want the Mac and macOS to continue to steadily improve. I love the platform. I am utterly apathetic towards Windows, and using Linux for 8 hours a day at my day job has confirmed that I could not possibly stand to run it full-time on my personal machine. I don't want the Mac to die off. But for the love of god I wish they'd just wait until the software is ready before releasing it.


It's temping to treat this as more of the same "Catalina is buggy, Apple is doomed" news, but note that Mail.app has ALWAYS been less than rock solid. For some reason, it seems to be a prime target for new features and reconfiguration every release, resulting in a lot of churn which unsurprisingly brings about bugs like this. A cursory search indicates a bug about some messages not showing up in 10.8, a Gmail issue in 10.9, VIP issues in 10.11, etc. But hey, we have gratuitous, cannot-be-disabled window animations when replying to a message, so what's a little data loss compared to that?


Is there a way to detect if you have data loss? It sure looks like Mail has my emails, but I'm not sure…


Perhaps if the mail database were blockchained or at least merkle tree linked or otherwise metadata secured.


Or just backed up.


A hash tree for email actually seems like a semi-decent idea for verifying integrity of a synced mailbox.


So use a hash function like in the olden days.


The benefit of either a tree or a sequence or hashes is that you could identify where and when the active mailbox differs from the backups. If each message is its own separate file then it's less interesting.


My iCloud backup, with years of data, including apps which only had local storage, was completely borked when I upgraded to iOS 13 (on my iPhone XS). My phone would enter a boot loop during the iCloud restore process, and I tried 15 different restores (different iOS 13 versions including beta versions, iTunes backups, a couple different types of restores they have at the Genius Bar, a direct phone-to-phone restore, curating my iCloud backup with only the most important apps, etc). None of them worked, all ended in a boot loop. Apple Support basically gave up on me, telling me my "backup was corrupted".

In the end I had to start with a fresh iOS install, which was very disappointing, as my years of accumulated app data were lost. I manually backed up what I could, but some apps had their data lost forever, and I wasted many hours of time.

Very disappointing.


    I feel your pain. I hope you remember in the future:

    Unless a backup can be verified, it is not a backup.

    Backing up to a complex or binary format is trouble.


So true, but I’m not sure what I could have done here, except stay on iOS 12* indefinitely. This wasn’t a case of having an invalid backup per se (I was able to restore my phone back to iOS 12), this was a case of being unable to port forward data from iOS 12 to iOS 13. In other words, a perfectly working system could not be upgraded via Apple’s upgrade process, nor did Apple provide good workarounds for this scenario, such as allowing the restoration of individual apps.

That’s why I’m extra disappointed in Apple. I did everything by the book, including testing my backups, and my data was still lost.


I think what you can do now is avoid complex, binary, and/or proprietary formats for your data, because they are more difficult to back up and restore.

You can also learn to not trust software which promiess you the world, but doesn't let you see its internals.


Yeah, lesson learned. Fortunately my most critical data was backed up elsewhere. This seems like an inherent issue with iOS, I will consider migrating to a different platform. Any suggestions other than Android?


See which iOS apps can export/import plaintext or other common formats, especially in an automated way.


It’s a good idea to create a bootable backup and come up with a clean install of macOS with each major release. Every time I updated the existing system straight up, I had minor or major issues solved by a clean install.


good LORD

if this is true how are we supposed to trust apple with our information?

BTW since updating my iPhone & iPad to iOS 13, and my desktop to MacOS 10.15, the Notes app does not propagate changes unless I force-quit the app and then restart it.

Entering a new note, and quitting the app, the new note does not propagate to my other devices. If I re-open the Notes app then the update happens. WTF

A walled garden ecosystem’s main raison d’etre is for everything to work together. If it doesn’t, it defeats the purpose.

I’ve been an Apple advocate for a long time but things are getting dicey. Perhaps my macs will turn into defacto expensive chromebooks. In other words use them to run chrome and in turn gsuite everything, and nothing else.

God awful


I've also had issues with the iOS 13 on an iPhone X. Mail notifications appear but the messages don't download for 30+ seconds, and sometimes notifications don't disappear.

Other people are also having issues with mail on iOS: https://twitter.com/CliffordAsness/status/118240716828649472...


Just got an 11 Pro and some notifications don’t vibrate, other notifications no longer show up even though they have permissions to and are set to. Sometimes iMessages won’t vibrate either.

It’s a mess and I can’t trust my phone to notify me. Now I have to constantly be checking it


Add in that alarms randomly don't fire, or fire at the wrong volume. I'm using my old phone as my clock and timer. I wonder if it's related to the bonkers notification settings.

Either way, disaster of a phone, and disaster of an OS.


Oh yes! Notes failing to sync after iOS 13 update is something that happened to me too. And apparently other people as well, as posted on Apple's forums: https://discussions.apple.com/thread/250684880


A walled garden’s raison d’être is to ensure that the garden’s owner makes as much money as possible.


I don't know if Apple has changed the format again, but in the past at least it seemed reasonably sane and filesystem-based:

http://mike.laiosa.org/2009/03/01/emlx.html

https://wiki.fileformat.com/email/emlx/

It doesn't seem that hard to write some more tools to manipulate them.


I have had code to handle emlx for over 10 years:

https://taoofmac.com/space/blog/2008/03/03/2211

The thing here is that

a) there are also a number of SQLite databases that are used by Mail to store metadata and sundry

b) Mail's IMAP handling has been notoriously buggy at times

My guess is that this particular data loss bug in Catalina stems from a combination of the IMAP implementation and the metadata storage, but since they keep playing whack-a-mole inside ~/Library/Mail, I can't offer more details.


> Moving messages between mailboxes, both via drag-and-drop and AppleScript, can result in a blank message (only headers) on the Mac. If the message was moved to a server mailbox, other devices see the message as deleted. And eventually this syncs back to the first Mac, where the message disappears as well.

Actually this was already a problem on Mohave. I lost all my mail from one mailbox when moving messages from one folder to another (gmail)


Why do people use Mail? (genuine question)


It's very fast (native app), it supports practically every type of mail account ever, everything can be stored locally (great for offline batch processing of emails), and there are keyboard shortcuts for everything. It takes a bit of customization to get a layout that works nicely for my workflow (I use the classic layout).

There are a bunch of other 'efficient' mail apps, but if you just need basic features and don't go for some exotic or trendy workflow, Mail works fine.

I don't upgrade to the latest OS for at least a few weeks, though, because if something like this is systemic, it will be fixed in the .1 or .2 release.

Also, always keep at least one local backup (I have Time Machine for that), and at least one remote backup.


It’s also so much better for working with massive amounts of mail compared to Gmail and other webmails. In Mail I can work through many tens or hundreds of messages quickly and easily. With Gmail I often feel like I’m jumping through hoops to do the same thing.


A use Mail.app but to be fair. Search in mail.google.com is much faster than in Mail.app (when you have thousands of mails)


I’ve never figured out how to force Apple Mail to download ALL attachments. How do I do this? In my experience it never downloads ALL of them and when you’re offline and click on a very old message it will not have the attachment unless you go online.


You can set this preference by going to the Mail menu > Preferences > Accounts. Select the account you want to adjust on the left, and in the first "Account Information" tab, there should be a pop-up for Download Attachments: [All, Recent, None]. The default for newly added accounts is "Recent".


The preference doesn’t actually do what it says, as mentioned in the original post. Starting with macOS 10.12, it doesn’t always download all the attachments, and even ones that did download (because you viewed the message) may get purged later.


Like the other comment says, this does not work, unfortunately. It’s supposed to work but it does not, and I’ve easily verified this.


I don't know if it's still true, but until about Snow Leopard I could have a smooth keyboard driven experience that completely aligned with other apps such as NetNewsWire.


It has a simple and pleasant native (non-web) interface that works consistently across devices and comes with the OS. It doesn't have many features, but all I want is to send, receive and organize e-mail in folders. I don't need a splash/welcome screen, extensions or built-in calendar/reminders. Honestly, I wish more apps were like this.


> Honestly, I wish more apps were like this.

It's really hard to find apps like that, and I often feel like it's getting harder as time goes on.


The best feature is (for me anyway) it's fast and works consistently across all my devices. I've yet to have a reason to move to anything else.

If I was someone continually running into issues as some seem to continually have happen I might not feel that way, but I've been on the Catalina and iOS 13 betas and thankfully even with the betas didn't have issues.

EDIT: I did have earlier versions of the iOS betas duplicate draft messages. Which lead to confusion and double sending since at first glance it looked like like I hadn't sent a message in drafts; once I figured out what was going on I would just check my sent to make sure I sent it before deleting the dupe in drafts. At least it wasn't a data loss bug.


It's built-in, fast, and works for what I need. Which is mostly skimming newsletters and then deleting them.

When I need a more featured alternative to something I'll use one (Things instead of Reminders, OneNote instead of Notes, VLC instead of QuickTime, etc) but email hasn't been one of those things.

Is there a reason that I should be looking at Mail alternatives? What important features is it lacking?


1. It comes in the box.

2. It allows me to have 7 inboxes routed to one view

3. It's pretty fast.

4. While "boring", It usually" just works.


Looks decent, doesn't hog obscene amounts of memory (for me - I know others have different experiences, and this can vary based on more factors than worth explaining).

I also just use macOS/iOS Mail because FastMail can push notify to the clients, and FastMail's iOS app isn't ideal.


It’s built in, and it’s always worked fine. What do you recommend instead?

I’m not opposed to switching but everything looks pretty lousy, in terms of workflow and integration, and if I have to live with “pretty lousy”, then “zero cost” and “mainstream first-party offering” seem to be the way to go.


I've used Mail.app since my NeXT days, and besides familiarity it has the simplest UX that could possibly work (if it was actually implemented properly).

I have Thunderbird installed for accessing a large e-mail archive on my NAS (simply because it has more control over local copies of messages) and find it horribly clunky and un-Mac-like even today.

And none of the trendy, flashy "new inbox philosophy" apps that have come and gone over the years were any sort of an improvement.

Even though I work at Microsoft today and acknowledge that the Entourage dumpster fire was finally fixed in the modern versions of Outlook for the Mac, I still prefer Mail.app because of its simplicity and straightforwardness, and refuse to use anything else for my personal e-mail.

Which is why I won't be upgrading to Catalina until this data loss bug is fixed...


It’s the built-in email client.

And there’s nothing particularly wrong or bad about it (until now, maybe).


because it is a mail "app" and not a mail "service" that has access to my emails and sells my data.


Our CRM works only with Mail.app and we cannot use G-Suite Mail directly. (Gmail support is a longtime issue with Mail.app, Apple still does not use the API …)


You can get message: URLs using AppleScript which will open the mail. I paste these in my Orgmode files. This allows me to archive the mail (and keep my inbox clean) while still keeping track of tasks.


Native and I like it's rules better than Thunderbird.


What alternatives do you like?


what do you use? (genuine question)


you people are going batshit crazy over completely unsubstantiated report.

It even says,

> I don’t know whether these are due to Mail bugs or to other factors such as problems on the Mac or with the mail server.




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