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macOS 10.15 Catalina

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MacBook Pro (13-inch, 2016, four Thunderbolt 3 Ports)
MacOS Catalina 10.15.1

My iWorks apps (Pages, Numbers and Keynote) and also Preview display e.g. "The document xxx.pages could not be opened" when double clicking the relevant file. If I Restart, then opening works, but next time I log in, the same happens.

I ran Onyx, restarted with the shift key down, used Disk Utility to no avail. Anyone else observing this? Any solutions?
 


My iWorks apps (Pages, Numbers and Keynote) and also Preview display e.g. "The document xxx.pages could not be opened" when double clicking the relevant file. If I Restart, then opening works, but next time I log in, the same happens.
I have experienced this same issue, with a restart fixing it.
 


... My iWorks apps (Pages, Numbers and Keynote) and also Preview display e.g. "The document xxx.pages could not be opened" when double clicking the relevant file. If I Restart, then opening works, but next time I log in, the same happens. I ran Onyx, restarted with the shift key down, used Disk Utility to no avail. Anyone else observing this? Any solutions?
Try deleting the Finder .plist and any other appropriate plist files using the following method. This was a common fix in the pre-OS X days (i.e. Mac OS 9 and below) and was discussed in macReports today.

Drag this file to Trash:
~/Library/Preferences/com.apple.finder.plist

Restart your Mac and try opening the file.
 


I decided to dip my toe in Catalina's waters. Installed it on a peripheral machine - a new 13" laptop that's not essential to my work flow.

Mostly, it went well, despite a few, predictable glitches that I was able to figure out and fix quickly. Here's one that's really giving me pause, though, from installing it on my other machines: I cannot boot from an external clone. This is core functionality that I have had no issues with for years. And, in order to encrypt an external clone, you need to be booted from it, then turn on FileVault.

When I went to Mike Bombich's "why won't my external clone drive boot" page, there are a ton of conflicts and issues listed.

Bottom line, I'm not doing anything on another machine until I can figure this one out. Trust me, I have tried a few of the most basic things already and no dice. I'll keep at it when I have a day of my life I can waste forever. Ugh.
 


Mostly, it went well, despite a few, predictable glitches that I was able to figure out and fix quickly. Here's one that's really giving me pause, though, from installing it on my other machines: I cannot boot from an external clone. This is core functionality that I have had no issues with for years. And, in order to encrypt an external clone, you need to be booted from it, then turn on FileVault.
When I set up Carbon Copy Cloner on my new 16-incher last night, I got a warning about the same thing but also a tip that it can be fixed by restarting in recovery mode (command-R), then from the Utilities menu selecting an option whose name I forget, but it's clearly related to start-up security. There is a radio button to allow start-up from an external drive there.
 


Here's one that's really giving me pause, though, from installing it on my other machines: I cannot boot from an external clone. This is core functionality that I have had no issues with for years. And, in order to encrypt an external clone, you need to be booted from it, then turn on FileVault.
Mike Bombich - one of my favorite software developers of all time - has a great page with stuff detailing this issue. Turns out, I just found a way to make it work.

Not sure I figured out the cause but, in my case, the first time I tried to do it was from a Sandisk Extreme 2TB drive that I had partitioned. I had been able to boot from this partition on Mojave with no problems. I did the same thing on a Samsung T5, which apparently has caused some people problems, but this drive was not partitioned, and it worked like a charm. I wiped it, reformatted it, then booted from it, turned on FileVault and rebooted from the normal startup drive. It's encrypting now.

I know there are some bugs in Catalina, and I will probably leave my 2012 cheese grater Mac Pro 5,1 alone for now, along with my other MacBook Pro, but so far I'm heartened. Another worry would be how it would handle the 20,000 plus songs I had laboriously ripped from my CDs over the years, but that has been smooth, as well. Not doing some full-throated endorsement of Catalina here, but so far, so good.
 


Ric Ford

MacInTouch
... the first time I tried to do it was from a Sandisk Extreme 2TB drive ...
This may or may not be related, but might be worth noting: I bought a Sandisk Extreme SSD and, fortunately for me, used SoftRAID's Certify function to check it before putting it into production: it failed. I returned it to Amazon, and I will not buy any more of those (though I bought one other that has worked, so far – I don't use it much and do extra reliability checks on it).

I have a bunch of Samsung T5's, and they've all passed certification without problems, along with many other SSDs and hard drives of all kinds.
 


Thanks, Ric. I know the Sandisks are not as reliable. In fact, I think I got that from a post of yours once. Still, that sucker, partition and all, did always work as a boot drive. I don't know much, but I suspect that Catalina may have had a problem booting from an external drive with a partition. Anyway, so far, so good. Thanks for all you do and I'll remember to use your Amazon link the next time I get a Samsung T5!
 


And, I guess the next thing I have to do is test the Sandisk with no partitions to see if that works. Just don't have time to do that tonight.
 


Ric Ford

MacInTouch
And, I guess the next thing I have to do is test the Sandisk with no partitions to see if that works. Just don't have time to do that tonight.
Well, there has to be at least one partition, right? If you have a chance, I'd be interested in seeing the output of these terminal commands:
Code:
diskutil list
diskutil coreStorage list
diskutil apfs list
(For reference: diskutil - Manual for macOS)
 




Sure, that should work.
I'll get to it later today. Mike Bombich does not think it was the partition, but I sent him the log, upon his request, and I'll update you if I hear back from him.

Sadly, my main communications machine, a 2019 MacBook Pro 15", revealed a broken speaker last night, so I had to do a lot of transferring of stuff and setting up another machine late, then wiped and reinstalled a vanilla OS on it today, so that I could bring it in for warranty work. Ugh.
 


Not sure I figured out the cause but, in my case, the first time I tried to do it was from a Sandisk Extreme 2TB drive that I had partitioned. I had been able to boot from this partition on Mojave with no problems. I did the same thing on a Samsung T5, which apparently has caused some people problems, but this drive was not partitioned, and it worked like a charm.
So much for my data point. I booted from the same partitioned Sandisk drive tonight, but from another machine - MacBook Pro 15" that was Catalina native from the start - and it worked fine. Booted, turned on encryption, etc. Not sure why it would not boot from the other machine. They were both relatively similar machines. Biggest difference to me is that one was upgraded from Mojave and the other was always Catalina. That being said, I'm tired, so I'm going to sleep on it.
 


Here's a "good news" Catalina adoption story. Apologies in advance for its length. It will be of interest, probably, to only a few people.

Like many, I had been waiting before adopting (better word than "upgrading," maybe?) Catalina from Mojave. I had some projects dependent on old 32-bit software (Adobe CS6, and a favorite old app, QuickTime 7). Plus, the first versions of Catalina seemed to have lots of bugs. So I waited. (At the end of this long note, I offer a few observations about running Catalina.)

When Catalina 10.15.1 was issued a couple weeks ago, I decided to take the plunge, with my 2017 iMac 27". But I wanted to preserve my ability to run some 32-bit software, just in case I needed something. I wanted to find a way to maintain a Mojave system to accomplish that, even as I adopted Catalina for everyday use. Plus, I'm "virtualization phobic" because virtualization just seems too complicated for me to maintain (probably I'm wrong about that, but that's what's in my head, anyway).

I'm going to give you the "headline" first, then offer some (longish) details for those who might find it useful.

Headline: Mission accomplished! Successfully!
Running a very stable version of Catalina (10.15.1), with a Mojave system safely embedded on the same internal (not external) drive, I'm able to reboot at will between the two systems, and am able to run 32-bit software from the Mojave system if/when needed, then switch back to Catalina.

The details:
  1. Of course, I created multiple backups of my iMac's internal SSD (2TB), using Carbon Copy Cloner, to two different external drives, and set those aside. I also ejected and unplugged all other external drives (Time Machine, CCC, other files, etc.) so as to prevent any of them from somehow becoming "contaminated" by my experimentation with Catalina and APFS.
  2. Throughout the following narrative, I "restarted" or "rebooted" using the Option key upon startup, selecting the appropriate startup volume.
  3. I shut down my iMac and booted it from a bootable Mojave external drive. This drive also contained a copy of the Mojave Installer file.
  4. Using the Mojave (external) system's Disk Utility, I completely erased my iMac's internal SSD.
  5. Still running from the external Mojave drive, I selected the Catalina "Upgrade" from the nagging "upgrade" under the Apple menu. Of course, that downloaded the Catalina installer. When the Catalina installer completed downloading and launched itself (expecting to install itself on my Mojave drive), I quit the installer and moved it out of the Applications folder of the Mojave drive, so it wouldn't auto-launch again.
  6. Still running from the Mojave external drive, I also copied the Catalina installer to yet another external drive, as a "safe" backup. (This was probably an unnecessary step, but I wanted to have flexibility about my later installation.) I also created a bootable Catalina installer drive on a USB stick.
  7. Still running from the Mojave external drive, I connected yet another "spare" external drive, and proceeded to install Catalina on this external drive. The installation went smoothly. I had created a bootable standalone Catalina drive.
  8. Next, I shutdown the computer from my Mojave drive, and restarted from my bootable Catalina external drive. The startup proceeded normally. (I had to create an admin "user" on the new Catalina drive, of course.)
  9. Now running from the external Catalina drive, I launched Catalina's Disk Utility. Naturally, my "blank" iMac internal SSD appeared as an empty, mountable drive.
  10. Still running from the external Catalina drive, using its Disk Utility, I again "erased" the internal iMac SSD.
Here's where I proceeded very carefully to prepare my internal iMac SSD to host my hoped-for dual-boot systems.
  1. Using Disk Utility (still running from the external Catalina drive), I "formatted" my internal SSD as "APFS." (This involved selecting "GUID Partition Map," then choosing "APFS" and entering a new name for the iMac's internal SSD, then clicking "Erase.")
  2. The internal iMac SSD now appeared in Disk Utility with the name I'd given it, as a single "container" with a single "volume" within it.
  3. Now I created a second "container." Carefully ensuring I was selecting the correct disk (the internal iMac SSD) in the list on the left, I clicked on the "Partition" tool. Upon request, I confirmed that I wanted to create a new "Partition."
  4. In the drop-down sheet that followed, I was able to "partition" my internal iMac SSD into two distinct "partitions." I chose to create a 40GB partition which would later host my "Mojave" system, and devoted the entire remaining (1.6 TB) partition to what would later become my everyday Catalina system. I named the smaller paritition "Mojave System," and named the larger partition the same name I had given the entire internal SSD. (I had to click "Apply" to complete my scheme.)
  5. Disk Utility now showed me two "containers," each with its own distinct single "volume." Each of those "volumes" was named as I had decided, including my "Mojave System" named volume.
Next steps: Installing different macOS versions on each volume:
  1. Still running from the external Catalina drive, I launched the Catalina installer. I proceeded very cautiously so as to be sure I would be installing Catalina on the newly-created APFS-formatted internal iMac SSD, and to be sure I was installing it on the larger of the two SSD "containers."
  2. The Catalina installation proceeded without a hitch, and pretty quickly, considering that it was a completely "fresh" install on a completely "clean" SSD uncluttered by previous-system user files or applications.
  3. I shut down and booted from the new "virgin" Catalina installation on the iMac internal SSD. No problems. When the startup completed, I saw my (empty) "Mojave System" drive appear on the desktop, a reassuring moment. Catalina was running fine.
  4. Next, I restarted, but booted again from my external Mojave system drive. When its desktop appeared, I could see the internal iMac SSD appear, plus its "Data" drive, plus my empty "Mojave System" drive.
  5. Running now from the external Mojave system, I launched the old Mojave installer. I told it to install Mojave on the (empty) "Mojave System" drive I had created on the iMac's internal SSD. The installation proceeded smoothly.
  6. When the Mojave installation on the internal SSD was complete, I restarted, selecting the "Mojave System" drive from which to boot.
  7. The iMac booted just fine running Mojave from the internal SSD's "Mojave System" partition. I created a new admin user for that partition. The other partition of the internal drive, the Catalina partition, appeared on the Mojave desktop, as did the Catalina "Data" partition. I ejected/disconnected all external drives.
  8. Notably, while running from the Mojave System partition of the SSD, I was easily able to access everything on the Catalina partitions, including everything in the Applications folder. For me, this was another immensely reassuring moment.
  9. Next, I restarted and booted from the iMac's internal SSD's Catalina partition. At this point, the SSD contained none of my previous user files or applications. It was still "virgin."
  10. Now running Catalina from the internal SSD, I launched Migration Assistant and told it to "migrate" all my user files and applications from one of the CCC backups I had created just before this operation began. Migration took a while but proceeded smoothly. It imported my users, system preferences and applications from my backup onto the Catalina partition of the internal SSD.
  11. Note that I did not perform a "migration" to the "Mojave System" partition. No need, since I had previously (above) determined that when running Mojave, all the folders on the Catalina partitions would be accessible.
  12. Just to be sure, after the migration, I rebooted from each of the Catalina and Mojave partitions of the iMac's internal SSD.
Mission accomplished! A few "afternotes:"
  • I have successfully booted from both system partitions, running from the same internal SSD — separately, of course, not at the same time. This, I presume, is the difference between my setup and "virtualization." I'm OK with it.
  • I have successfully run 32-bit applications, from the Applications folder of the Catalina partition, while running Mojave from the Mojave partition. This was a crucial confirmation for me.
  • I have successfully opened documents from the Catalina partition while running Mojave from the Mojave partition. (For instance, I opened-and saved an Adobe Photoshop document from the Catalina partition while running the 32-bit Photoshop from the Mojave partition.)
  • I have since realized that the applications residing in the Catalina partition seem to appear within the Applications folder of the Mojave partition, though they were not copied to the Mojave partition. This seems to be part of the "magic" of the Catalina APFS system. Mojave can "see" those applications, and appears to have those applications within the Mojave Applications folder... even though they are not on the Mojave partition.
  • My dual-boot Catalina/Mojave iMac seems completely calm. No puzzling reboots, no crashes. Following this procedure, I needed to update several scripts for my backups in Carbon Copy Cloner and Chronosync, which, of course, needed to learn the new locations of source files and destination backups.
  • Accessing user files from the Mojave System partition has a "permissions" twist: Naturally, the admin user on the Mojave System partition is not allowed even to "see" protected user files on the Catalina partition. Possibly, I could find a way to override this, but I think it's a good security feature. Since I mostly need to access only a few user files for occasional work with legacy 32-bit applications, I plan to copy those files to an external drive or USB drive, where they can be accessed while running the Mojave system. The modified files can then be copied back to the Catalina system.
A few observations about running Catalina 10.15.1, now, for about two weeks:
  • I have not experienced any loss of iTunes music or music data... so far. (I'm not a big music user, so maybe a revelation is yet to be disclosed.)
  • I have not experienced any disappearance of any of my photos in the Photos application. Everything seems to be as it was (of course, there are some new features in the Catalina version of Photos, but my user files seem to be all there).
  • I have not experienced any loss of Apple Mail, or any problems with my several different email accounts... all of which are showing up just fine under Catalina. Probably I haven't noticed yet, but whatever changes have taken place in Mail have not hit me in the head yet. (I actually was a user of Mail's "stationery" feature, and I will miss that, a bit. But it's not a showstopper for me.)
  • In short, for me, the switch to Catalina has been pretty smooth. Nearly flawless. I'm still futzing with some preferences and notifications, etc. But nothing unnerving.
  • I have not felt troubled by a raft of "permissions" or "authentication" notices. Yes, upon the first few startups under Catalina, I had to modify "authentications" for several apps... especially for those which create screen grabs or otherwise want to use "access" to things Catalina is defending. But once those were done, Catalina has not intruded unexpectedly.
  • My overall positive experience led me to also adopt Catalina 10.15.1 on my MacBook Pro (late 2013, 13" retina). I did not create the dual-boot scenario on the laptop. Having access to the old 32-bit apps on my iMac is enough. On the MacBook Pro, I used "Go64" to eliminate almost all 32-bit software, including tons of Adobe detritus which had accumulated over many years through several previous versions. This "housecleaning" on the laptop felt good! ;)
 


Ric Ford

MacInTouch
Here's a "good news" Catalina adoption story. Apologies in advance for its length...
That's an outstanding report, Ralph – thanks for writing that all up; there's really a lot there, and you did an admirable job of managing all the details and issues.

There's probably a lot more for all of us to pursue further, but there were a few things that bobbed up to the surface for me:
I also ejected and unplugged all other external drives (Time Machine, CCC, other files, etc.) so as to prevent any of them from somehow becoming "contaminated" by my experimentation with Catalina and APFS.
That's exactly the right thing to do, but one subtle caveat: as we've noted previously, simply running an Apple software update – a Catalina installation or a Mojave security update, for instance – can (and often will) change the firmware inside your Mac. Thus, though you have protected your clone drives from being changed, you're still making a permanent change to your Mac (i.e. its firmware) by installing Catalina, even if you subsequently erase your internal drive and clone back from the backup. Now, I don't know of any specific problems caused by the firmware updates, but I think it's important to understand these mechanisms and changes, which are invisible to the user.
I have since realized that the applications residing in the Catalina partition seem to appear within the Applications folder of the Mojave partition, though they were not copied to the Mojave partition.
This seems very strange to me, but I haven't experimented with Catalina, so I may well be missing something. I'd be interested to hear if others can confirm the behavior or explain what's going on there.
Accessing user files from the Mojave System partition has a "permissions" twist: Naturally, the admin user on the Mojave System partition is not allowed even to "see" protected user files on the Catalina partition.
Again, I haven't worked with Catalina, but I'm curious about what's going on here, because I can certainly access all the files on a backup clone drive while booted from a different drive, and I'm not sure why you can't access your files on the Catalina volume when booted from Mojave, which is a similar situation.

Perhaps you created a new user in Catalina first, then later migrated your Mojave system and this created different UIDs (User IDs in the Unix-based file permissions system) for your documents, because the usual first User ID, UID 501, was already taken. If you were offered the chance to import/migrate another system at the first boot of Catalina, before ever reaching the desktop, this problem might possibly be avoided. (That's the case in older macOS systems; I don't know about Catalina.)

Absent that option, you may be able to create a permission "group" that includes both your first Catalina user (UID 501?) and your original user (now UID 502?), so they can share files. But I'm just speculating here, and other folks may have more/better information. I just wanted to give you a potential clue. Here's some related reading from the late great Pondini:


#UID #501 #JamesPond #TheGreatPondini #migration
 


Ralph Begleiter said:
I have since realized that the applications residing in the Catalina partition seem to appear within the Applications folder of the Mojave partition, though they were not copied to the Mojave partition.
This seems very strange to me, but I haven't experimented with Catalina, so I may well be missing something. I'd be interested to hear if others can confirm the behavior or explain what's going on there.
Haven't looked closely, but Ralph Begleiter's conjecture that "[t]his seems to be part of the 'magic' of the Catalina APFS system" is confirmed by:
macOS 10.15 Catalina: The Ars Technica review
...
Volume groups, firmlinks, and why most people won’t notice any of this stuff
APFS in Catalina supports something called “firmlinks,” as a way to maintain macOS’ existing directory structure despite everything now being spread across two volumes. Think of an alias in macOS or a shortcut in Windows—these are forms of symbolic links (or symlinks), small files that can be stored anywhere and which point you toward another file on another volume, partition, or disk. But where symlinks only go one way, firmlinks are bidirectional. Folders can appear in multiple places, but from the Finder’s perspective and the user’s perspective, neither directory is the “real” one and neither is the “shortcut.”

… Look at the contents of either /Applications or /System/Volumes/Data/Applications, and you’ll see that the only applications actually stored in that folder are the ones you’ve installed yourself, plus Safari (presumably to make the browser easier to update on its own without a major system update). But the Finder still shows the user their installed applications plus all of the regular macOS system apps in the same folder.
 


Ric Ford

MacInTouch
Haven't looked closely, but Ralph Begleiter's conjecture that "[t]his seems to be part of the 'magic' of the Catalina APFS system" is confirmed by macOS 10.15 Catalina: The Ars Technica review, Volume groups, firmlinks, and why most people won’t notice any of this stuff
Right, that trickery is part of macOS Catalina, but it doesn't explain why the Mojave system would display Catalina's Applications folder as if it were Mojave's own Applications folder. There seems to be some confusion here, and I can't quite sort out what's going on.
 


Right, that trickery is part of macOS Catalina, but it doesn't explain why the Mojave system would display Catalina's /Applications folder as if it were Mojave's own /Applications folder. There seems to be some confusion here, and I can't quite sort out what's going on.
I will investigate further and report again (probably not immediately).

I'll also try to check out your UID suggestion. (I'm not even sure where/how I would "see" those numerical UIDs. Don't think I've ever seen anything like that before.)

In this connection, however, I am able to easily access my user files on an external backup drive... just not on the internal SSD, where I see the folders and files, but with Apple's "Do Not Enter" icon signifying "no permission" to view. I hadn't thought about trying to create a "user group" to allow that. I'll give that a try and report back.

As always, thanks!
 


I will investigate [Mojave/Catalina Applications folder oddities] further and report again (probably not immediately).
Web search turns up
Carbon Copy Cloner (Bombich) said:
Working with APFS Volume Groups
Finder shenanigans with the Applications folder
which might be helpful.

My lightly-informed guess is that Catalina APFS and Mojave APFS are no different in this scenario. Good luck.
 



I'll also try to check out your UID suggestion. (I'm not even sure where/how I would "see" those numerical UIDs. Don't think I've ever seen anything like that before.)
The easiest way to check those is to go to the Users & Groups settings in the System Preferences. Unlock the settings and then right-click on the user account you are interested in. You will get an option to go to the "Advanced Options".

The Advanced Options will show you all the underlying information about that account. Would recommend against making any changes, just use this for information gathering only. You can get into serious trouble making changes if you don't know exactly what you are doing and why.
 



Here's a "good news" Catalina adoption story. Apologies in advance for its length. It will be of interest, probably, to only a few people.
Thank your the detailed information, as I am planning to convert my Mojave system to Catalina in another month or so but also need the ability to run a couple of 32-bit apps. You created a dual-boot system by partitioning your internal disk. Couldn't the same result be accomplished by creating a second volume in the APFS container, installing Mojave on it, and then updating the original internal Mojave volume to Catalina?
 


... Couldn't the same result be accomplished by creating a second volume in the APFS container, installing Mojave on it, and then updating the original internal Mojave volume to Catalina?
That should work. I did the same thing when I was trying to debug not being able get into recovery mode on my 2018 Mac Mini. Both macOS 10.14.6 and 10.15.1 seemed to work fine, but I didn’t check how 32-bit apps worked before I deleted the Catalina volume.
 


I've only got one Mac (2012 MacBook Pro) to try this on, but I cannot get an external drive to boot Mojave 10.14.6 on my MacBook Pro with Catalina OS 10.15.1 installed on it.
 


If you have trouble getting an external USB drive to boot, make sure you try plugging it directly into a native Mac USB port. Sometimes (always?) a USB hub will prevent the boot capability.
 


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