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Can't mount encrypted disk images after Monterey upgrade

I have some encrypted disk images I've been using since 2007 to store health, financial records, etc.. and I can't open them since I moved to macOS 12. I waited until 12.1 avoid some of these bugs.


I just get a message "The disk image couldn't be opened - The disk image is corrupted" when I click on the .dmg file. I have backups in time machine and backblaze, I can't open the backups either.


I did notice that I can "hdiutil attach <path to dmg>" in Terminal - and it prompts me for the password, mounts the DMG and then I can access everything normally via Finder. So I don't believe the disk images are corrupt. This same issue is happening to several encrypted disk images I have.


Any ideas what the problem is? This is only similar post I found: https://discussions.apple.com/thread/253490294

Mac mini, macOS 12.1

Posted on Jan 4, 2022 1:49 PM

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Question marked as Top-ranking reply

Posted on Jan 30, 2022 12:37 PM

I have a similar, but not idential, issue to to David Carlin's. I have an encrypted DMG that I've used for many years. It contains sensitive financial information. It worked fine on my old Mac, but I recently purchased a MacBook Air running OS X Monterey 12.1, and when I click on the DMG to open it, it asks me for my password as usual. I enter the password—it is the correct one—and nothing happens. No error, no nothing. It does not mount. I was wondering if there was somehow a password issue, so I typed in an intentionally incorrect password, and the password window reappeared, signaling that the previous password was incorrect.


The file is stored locally, and to be sure, I moved it to my Desktop and tried mounting it, but no dice. It does not appear in Disk Utility under any circumstances.


This is quite vexing. I hope Apple releases an update in the future for this bug.

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6 replies
Question marked as Top-ranking reply

Jan 30, 2022 12:37 PM in response to David Carlin

I have a similar, but not idential, issue to to David Carlin's. I have an encrypted DMG that I've used for many years. It contains sensitive financial information. It worked fine on my old Mac, but I recently purchased a MacBook Air running OS X Monterey 12.1, and when I click on the DMG to open it, it asks me for my password as usual. I enter the password—it is the correct one—and nothing happens. No error, no nothing. It does not mount. I was wondering if there was somehow a password issue, so I typed in an intentionally incorrect password, and the password window reappeared, signaling that the previous password was incorrect.


The file is stored locally, and to be sure, I moved it to my Desktop and tried mounting it, but no dice. It does not appear in Disk Utility under any circumstances.


This is quite vexing. I hope Apple releases an update in the future for this bug.

Jan 5, 2022 5:55 AM in response to CharPatton1

I ended up making new encrypted disk images and copying everything over. I took this as an opportunity to use sparse image instead of fixed size read/write images to save on disk space. The new encrypted images also show up as "version: 2" in "hdiutil isencrypted" output. I'm guessing Monterey Finder isn't capable of opening anything else.

Jan 6, 2022 5:40 PM in response to David Carlin

Good idea. I will likely wait a bit to see if Apple fixes the bug in a future iOS update before going to the work of making new ones.


Three questions:

  1. Are you happy with sparse disk images? I had tried them a few years ago and they behaved kind of squirrely so went back to the old kind.
  2. Did you try mounting regular new disk images in Monterey, or just the sparse ones?
  3. My Drobo NAS images no longer work with Carbon Copy Cloner. The backups always fail (and they worked great in Big Sur and earlier). Does anyone think the issues are related?


Thanks!

Jan 4, 2022 3:49 PM in response to David Carlin

Also interesting is "hdiutil isencrypted <path to dmg>" output. I noticed all the images I cannot open via Finder report "encrypted-file-version: 1" and the images I can open are "version: 2"


The oldest images from are from April 2007 and I've been using them continuously - Created on my Titanium PowerBook G4 at the time, presumably MacOS X 10.4 Tiger. Worked fine w/macOS 11 Big Sur.

Jan 4, 2022 4:43 PM in response to David Carlin

It seems like you found a solution using Terminal commands in Monterey. Another approach could be using the Disk Utility and Terminal from a bootable installer of an earlier version of macOS such as Big Sur. The Disk Utility (or Terminal) could mount the disk image and then a Terminal CP command could be used to copy the data elsewhere. Finally, the Disk Utility could be used to re-encrypt using a newer encryption version.


By the way, I've had problems with Monterey creating disk images from folders residing on external devices. The workaround (assuming sufficiently available storage) is to copy the folder to the internal (system) device before running the Disk Utility. Alternatively, the same bootable installer technique (with Big Sur or earlier OS) would work without the need to copy the data.


- Pie Lover

Can't mount encrypted disk images after Monterey upgrade

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