Serious Monterey File-sharing bug

Here's fun:


1) From a Monterey client, connect to a share on file server. Any file server. Can be a NAS, windows box, macOS file sharing - what have you.


2) Open a file on that share by double-clicking it.


3) Move that file into a subfolder.


4) Try to double-click that file again and discover that... you can't.


Relaunching the Finder/disconnecting and reconnecting the server/changing the filename or filetype will make that file openable again. Moving it back to its original location will not. It's not a permissions issue - I've been down that road at length, culminating in pulling a brand new M1 iMac out of a box and putting it next to a freshly-wiped M1 MBA, turning file sharing on on the iMac, connecting to it from the MBA, making some blank .txt files on the brand new share, and watching everything fail.


Other versions of macOS do not show the same issue when connecting to the same file share. The issue is definitely with 12.5.1, but the client who alerted me to had the issue with 12.3 so that might have issues too.


I've been in touch with AppleCare - who have been helpful but don't have any information on this. Is anyone else seeing this problem?


Posted on Sep 8, 2022 1:47 PM

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Posted on Sep 8, 2022 3:03 PM

Excellent questions!


Yes, I can move a file before opening it and it'll work fine.


I'm reasonably confident that it's not the fault of the documents. To test the issue I made ten each blank .txt, .rtf, .psd and .jpg files, copied them to a file share, was able to open them just fine until they were moved. Also, I've tried accessing the same files and share with macOS 11.6, 10.15.7 and some flavor of Mojave that I don't recall right now. Everything worked as expected with those OSes.


If I open the file from within the app and then hit save then it will make that document accept a double click. If I open the file from within the app, make a change and save then it will also work. If I open the file from within the app and just close it again without making a change or saving, then it won't respond to a double-click.



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Sep 8, 2022 3:03 PM in response to Old Toad

Excellent questions!


Yes, I can move a file before opening it and it'll work fine.


I'm reasonably confident that it's not the fault of the documents. To test the issue I made ten each blank .txt, .rtf, .psd and .jpg files, copied them to a file share, was able to open them just fine until they were moved. Also, I've tried accessing the same files and share with macOS 11.6, 10.15.7 and some flavor of Mojave that I don't recall right now. Everything worked as expected with those OSes.


If I open the file from within the app and then hit save then it will make that document accept a double click. If I open the file from within the app, make a change and save then it will also work. If I open the file from within the app and just close it again without making a change or saving, then it won't respond to a double-click.



Sep 8, 2022 2:03 PM in response to etresoft

Ah. Apologies!


No error message. Nothing to see at all, really; double-clicking or selecting the file in the Finder and hitting Cmd-O or choosing "Open" from the file menu just does nothing. The file doesn't open, no application opens. Dragging the file to the appropriate dock icon works, as does opening the file from the appropriate application's "Open" dialog will work, though.


Which is fine, except that if you're dealing with a large number of files then calling the dialog box every time is extremely awkward.


Relaunching the Finder or renaming the file makes it executable once more, but again, large number of files, awkward etc.

Sep 9, 2022 10:27 AM in response to -RWX-

-RWX- wrote:
I've filed bugs and opened a case with the folks on the Enterprise Helpdesk.


It's not my intent to beat this dead horse any longer, but please be sure that you filed a bug report using the link etresoft provided.


Enterprise Helpdesk is unlikely to do anything more than lend a sympathetic ear.


It is my intent to let you know that's what I did with a similar bug in the past, and it was fixed within a couple months, at most. Apple may or may not be interested in continuing to do that, considering their overwhelmingly dominant market is fixated upon having the latest cool gadget.

Sep 9, 2022 9:39 AM in response to etresoft

I've filed bugs and opened a case with the folks on the Enterprise Helpdesk. So far it's been made clear that they're very nice and very sympathetic, and say that they have engineers looking at it, but without getting into the specifics it's also terribly clear that they're probably stretching the truth on that one. I'm not looking to hoist a pitchfork and rabble-rouse; I'm looking to see if anyone else is seeing this issue and if anyone has a workaround.


The client concerned recently bought eighteen M1 Studio Maxes with Studio Displays to replace their aging iMac Pros. It's a lot of money, and prompted the jump from Big Sur to Monterey (which is why its something that just got brought to my attention). I agree, that's a drop in the bucket as far as Apple's concerned, and I'm not naive enough to think that Apple owes anyone anything. You're right - those are misguided expectations, Think Different is a marketing slogan and not indicative of some ridiculous socio-emotional contract between a corporation and its fans etc etc. However, the fact remains that this is a chronic, simple, reproducible problem that impacts a lot of users.


It's not that the bug exists, it's just that it's so... basic. And shoddy.

Sep 9, 2022 10:19 AM in response to -RWX-

-RWX- wrote:

I'm looking to see if anyone else is seeing this issue and if anyone has a workaround.

As I said above, I was easily able to reproduce this bug. However, I had to configure my Linux server to run a file server first. Like the vast majority of Mac users, I don't have regular access to any file servers.


A workaround would be to look for alternatives to traditional file servers. The truth is, you really shouldn't be using those at all in the modern world. There is no better avenue to a large-scale ransomware attack than a file server. That alone should be a perfectly reasonable excuse to get rid of them. But going beyond that, there are other methods available to share data between users while improving your ability to control access and track changes.


I realize it is very hip these days find fault with Apple. However, it does appear that Apple has found a sweet spot that attracts more and more of the best users every year, while gently nudging existing users towards new solutions, and allowing more recalcitrant users to move off to other platforms and be some other company's problem.


Sep 9, 2022 4:48 AM in response to -RWX-

-RWX- wrote:

Fun update (and, admittedly, possibly not something that necessarily belongs here): the problem persists in the latest build of Ventura.

So that's special.

Discussions of betas are not allowed in these forums. If you can file a bug against Ventura, then you should do so. You stand a pretty good chance of getting it fixed in Ventura. At this point, it is relatively unlikely to be fixed in Monterey. It is cool to be the first person to discover a bug, but unless you discover it very soon after the first beta release, it is unlikely to ever get fixed. The fact that the bug lasted so long undiscovered is a testament to it’s lack of importance.

Sep 9, 2022 8:54 AM in response to -RWX-

-RWX- wrote:

While I appreciate your perspective on the matter, I'm not interested in devolving this into squabbling-on-the-internet; I'm interested in getting this addressed, because its the OS performing in an unexpected condition, it's a recent development, and it's a tangible real-world problem that is actually costing time and money. Writing it off as unimportant without considering those factors is reductive at best.

Just so we're absolutely clear on this - I have zero personal investment in finding a "cool" bug. There's no glory in having the people who pay you have to restructure deadlines to accommodate their files not opening.

I’m not “squabbling” at all. I’m just trying to manage expectations. The fact that you discovered this bug so late in the life of Monterey strongly suggests that few people were using it in this manner. Apple makes consumer devices. I understand when people manage a business where their employees use Apple devices that they have certain expectations about the value of their business to Apple. Those expectations are misguided. From Apple’s perspective, such customers are a tiny portion of their user base and a significant portion of their support expenses. It is an unrequited relationship.


If you haven’t already reproduced this bug in Ventura and filed a bug report through appropriate channels, I strongly urge you to do so at your earliest convenience. You have probably already missed the window to get the fix in the first released version of Ventura, but you might be able to make the 2nd minor release, maybe in February.

Sep 9, 2022 11:00 AM in response to -RWX-

-RWX- wrote:

That you were able to encounter the bug connecting a Mac client to a Linux server is an interesting data point, and not one that I'd seen so far.

It shouldn't matter. It isn't your job to research the bug and find out what causes it. No amount of Free Labour that you donate to Apple will influence their decision about whether or not to fix the bug.


Saying that the solution is to abandon using file servers is almost absurd, though. Yes, there are other workflows that bring value when used in the appropriate sized-workgroup, but there are large customer bases in organizations with considerable file assets that require collaborative, timely access.

There are always large customer bases using obsolete technologies. Every year, those technologies get more and more difficult to maintain. They require painful compromises. Your only choice in the matter is the method of torture.


Plainly, storage services and file synchronization have their place, but they don't scale to organizations that work with in multiple shares in the 40TB+ range run through 10GBe.

Sorry, but 40TB is not much storage. Years ago I worked for two different groups that maintained PBs of local storage. But even that is obsolete in today's world of cloud storage. So there's another workaround for you. You can move your data to S3, Azure, or half a dozen different providers. That gives you global distribution and probably saves a huge amount of money. Nobody ever got fired for using AWS.

I mean, I really take your point, but on the other hand when you see your doctor complaining that it hurts to bend your elbow, having him say "well, stop bending your elbow" isn't a practicable answer.

How about a brace to immobilize the elbow instead?

Sep 8, 2022 3:10 PM in response to etresoft

That's good to know. I mean, it's not good, but I appreciate knowing I'm not losing my mind here.


I've already been on the phone with the Enterprise Helpdesk folks, and they've been sympathetic and courteous and haven't really done anything about it for the last week or so except sort of shrug and mention off-handedly that maybe it'll be fixed at some point. I get the strong impression that they haven't actually bothered to actually look at it or make any effort to replicate the issue. Meanwhile I have clients whose workflow has ground to a halt.


It's less than ideal...

Sep 8, 2022 3:17 PM in response to -RWX-

That is the preferred method of copying a file to a second location, i.e. not opened. While you have it open in the original location you can do a save as to the new location and I'm sure it will work as intended.


Just so we're on the same page - you are copying the file to the new location and not moving it, i.e. dragging with the Command key held down.

Sep 8, 2022 3:24 PM in response to Old Toad

No, I'm moving the (closed) file, and not copying it. Either that, or the client selects the appropriate files they want to work with and chooses "make new folder with selection" from the Finder.


Said client - who reported this to me a week or so ago - is prepping a huge project for print and distribution, and their production department are moving (large amounts of) design files into folders and then finding they can't open them. This is a problem that at small scale is an annoying inconvenience, but at large scale (many thousands of files) this is turning into a major expenditure of time and money. They are... annoyed. And they're not shy about sharing that annoyance around, so their problem is very much my problem :)


Sep 9, 2022 6:51 AM in response to etresoft

While I appreciate your perspective on the matter, I'm not interested in devolving this into squabbling-on-the-internet; I'm interested in getting this addressed, because its the OS performing in an unexpected condition, it's a recent development, and it's a tangible real-world problem that is actually costing time and money. Writing it off as unimportant without considering those factors is reductive at best.


Just so we're absolutely clear on this - I have zero personal investment in finding a "cool" bug. There's no glory in having the people who pay you have to restructure deadlines to accommodate their files not opening.


Thanks for the note on discussing betas, though. Apologies. Won't do that again etc.


Sep 9, 2022 10:28 AM in response to etresoft

That you were able to encounter the bug connecting a Mac client to a Linux server is an interesting data point, and not one that I'd seen so far. I appreciate that.


Saying that the solution is to abandon using file servers is almost absurd, though. Yes, there are other workflows that bring value when used in the appropriate sized-workgroup, but there are large customer bases in organizations with considerable file assets that require collaborative, timely access. Plainly, storage services and file synchronization have their place, but they don't scale to organizations that work with in multiple shares in the 40TB+ range run through 10GBe.


I mean, I really take your point, but on the other hand when you see your doctor complaining that it hurts to bend your elbow, having him say "well, stop bending your elbow" isn't a practicable answer.

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Serious Monterey File-sharing bug

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