Apple Mail stopped working after upgrading to macOS Ventura

On the upgraded iMac the home volume is on an external APFS mirrored volume - the boot drive is too small. I have indeed moved the home directory to another volume and I’ve had tons of issues with Apple not properly supporting this. It would be disappointing that Ventura now removes support even further…

This is almost certainly the issue.

I would check this out…

https://c-command.com/spamsieve/help/resetting-mail-s-privat

I followed the instructions. The mailbundle is re-installed by DTp in the correct location but it is not visible from the Mail settings. I’m looking at clearing out all Mail settings.

Are you looking at Mail Menu: Main → Settings → Tab General → Button "Manage Plug-ins (at bottom left of that tab?

yes, as mentioned earlier, on my macbook the devonthink plugin shows, not on the imac

Interestingly, when the ~/Library/Mail/Bundles directory is not present, the settings do not show the option ‘Manage Plugins’. After DTP re-installs the bundle, and the Bundles directory exists, the ‘Manage Plug-ins’ button appears. However, when I click on the button, the list is empty (on my macbook it shows the DEVONthink mailbundle).

Listing the directory shows:

lodewijk@imac ~/Library/Mail/Bundles % ls -ltr
total 0
drwxr-xr-x  3 lodewijk  admin    96B Dec 20 15:51 DEVONthink_BigSur.mailbundle/
lodewijk@imac ~/Library/Mail/Bundles %

So it is clearly present… I can explore the whole directory from Finder, I’m at a loss what to do next…

To test the mailbundles, I installed spamsieve, and installed the plugin - that does appear in the “Manage plug-ins” menu. Interestingly, the SpamSieve plugin is not in the bundles directory, but in its own directory in ~/Library/Mail.

Even after clearing out all the Mail settings and reconfiguring, I don’t see the DEVONthink mailbundle

On my laptop, the plugin has also stopped working. In ~/Library/Mail I removed the Bundles directory and restarted mail, then restarted DTP and re-installed the plugin. When I then try to import mail, DTP get stuck with the spinning beach-ball.

This used to work… What changed?
The installed bundle is the DEVONthink_BigSur.mailbundle, dated July 20th, 2022 - this is the same bundle that is giving me grief on my iMac. The previous version seemed to work on my laptop.

Did you only install the plugin or also enable it in Mail > Preferences > General > Manage Plug-ins…?

And did you read the article from C-Command I linked previously?
As mentioned, Mail doesn’t like it when the home directory isn’t on the boot drive.

I’m testing on my laptop to make sure the Mail directory is on the bootdrive.

After removing and reinstalling the plugin, I go into preferences to enable the plugin and confirm that it has access to the Mail directories.

Hold the Option key and choose Help > Report bug to start a support ticket.

I think I solved the problem. Not only does Mail not like it when it is not on the boot-drive, it doesn’t like it when alternative paths are used. I’ve been using a synthetic mountpoint /map/bones to maintain consistency between my iMac (where my home directory is /Volume/apfs-ext/bones) and my macbook (where my home directory is /Users/bones).

After reverting the macbook to /Users/bones as path, instead of /map/bones, everything worked. Frustratingly, on both machines the Mail application works find with /map/bones. Could it be a hardcoded dependency in the plugin?

Summarizing:

iMac:/Volume/apfs-ext/bones : plugin does not work
synthetic /map/bones to iMac:/Volume/apfs-ext/bones : plugin does not work
synthetic /map/bones to macbook:/Users/bones : plugin does not work
macbook:/Users/bones : plugin works

Thanks for the follow-up!
Indeed you are doing something quite out of the ordinary here.

I can’t answer on any possible dependencies in the plugin, but @cgrunenberg would be the person who would know.

The plug-in doesn’t have any dependencies, it “only” needs to be installed, enabled & accepted by Mail.

I have the same problem - the Mail plug in no longer appears in mail preferences on my MBP. Nothing else has changed except the upgrade to Ventura. All DT3 files have always been on my internal hard drive.

I need a fix. I am not capable of sending you all the stuff you asked for above. Just help me.

Thank you

Stan Kramer - long time, 77 year old DT user.

You have two requests for help. Let’s just use this one and ignore your other post.

  1. Title if this post says stopped working after upgrade to macOS Ventura. Did you recently upgrade.

  2. In Menu: DEVONthink → Install Addins → does it show the Apple mail plug-in is installed?

  3. in Apple Mail Menu: Settings → Tab General → bottom left click on Plug-ins, is DEVONThink plug in shown and available?

  4. Have you by chance recently re-booted the machine? A good thing to do periodically. If not done recently, do it now and see if problem goes away.

Per other posts you can find on this forum, there are certain files you can delete via Finder, but we’ll do that later. @bluefrog can step in.

  1. no. but I recently started using DT3 again.
  2. yes
  3. “Plug-Ins” no visible anywhere
  4. of course I have.

has it ever worked since you started using again? If yes, then can you think of what might have changed when you saw the problem?

What version of macOS now in use, and what version of DEVONthink?

There is only one place: In Apple Mail Settings, Bottom left corner of General Tab, a button “Manage Plug-ins”. Button not there, or after you click on button you don’t see DEVONthink Plug-in?

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Also see your other post with suggestion from @cgrunenberg