brew services start fails when MacOS User Home Directory is on External Drive

[antiflash1]

Output of brew config

HOMEBREW_VERSION: 4.4.25
ORIGIN: https://github.com/Homebrew/brew
HEAD: f3bd91d3afe086824d24708230e1f0c7f943135a
Last commit: 18 hours ago
Branch: stable
Core tap JSON: 21 Mar 00:27 UTC
Core cask tap JSON: 21 Mar 00:27 UTC
HOMEBREW_PREFIX: /opt/homebrew
HOMEBREW_CASK_OPTS: []
HOMEBREW_MAKE_JOBS: 10
Homebrew Ruby: 3.3.7 => /opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.3.7/bin/ruby
CPU: deca-core 64-bit arm_donan
Clang: 16.0.0 build 1600
Git: 2.39.5 => /Library/Developer/CommandLineTools/usr/bin/git
Curl: 8.7.1 => /usr/bin/curl
macOS: 15.3.2-arm64
CLT: 16.2.0.0.1.1733547573
Xcode: 16.2 => /Volumes/Data/Applications/Xcode.app/Contents/Developer
Rosetta 2: false
johan@Internals-Mini ~ %

Output of brew doctor

Your system is ready to brew.

Description of issue

When I try to run any service using

brew services start <formula>

I get error

Bootstrap failed: 5: Input/output error Try re-running the command as root for richer errors. Error: Failure while executing; /bin/launchctl bootstrap gui/502 /Volumes/Data/Users/johan/Library/LaunchAgents/homebrew.mxcl.syncthing.plist exited with 5.

II understand that this error can have multiple causes, but none of the solutions I’ve found have worked for me. Since the error occurs with all formulas, I suspect the issue is related to the fact that I’ve moved my User Home Directory to an external drive, and the .plist file was copied to that external home directory.

Additionally, if I run:
sudo brew services start <formula>
the service starts without issue because the root home directory is on the internal drive. However, I don’t want to run it with elevated privileges.
MacOS requests "access to removable disk" when a program tries to access my home directory on the external drive, but I don’t get that dialog when I run the brew command.
I’ve tried giving "Full Disk Access" to Terminal, /bin/launchctl, and /opt/homebrew/bin/brew without success.

Any ideas?

[gromgit]

Does /opt/homebrew/var/log/syncthing.log show any errors?

[antiflash1]

No errors. I can run sycnthing without problems in terminal with /opt/homebrew/Cellar/syncthing/1.29.3/bin/syncthing.
It's only the launchctl that gives the error.

[gromgit]

How about /var/log/com.apple.xpc.launchd/launchd.log?

[antiflash1]

First thanks for your help in guiding me to the logs. Here is the relevant error from launchd.log
2025-03-22 22:49:19.504143 (gui/502 [100003]) <Notice>: Enabling service homebrew.mxcl.syncthing 2025-03-22 22:49:19.507486 (gui/502 [100003]) <Notice>: entering bootstrap mode 2025-03-22 22:49:19.507751 (gui/502/homebrew.mxcl.syncthing) <Error>: Caller specified a plist with bad ownership/permissions: path = /Volumes/Data/Users/antiflash/Library/LaunchAgents/homebrew.mxcl.syncthing.plist, caller = launchctl[11630] 2025-03-22 22:49:19.507762 (gui/502 [100003]) <Notice>: Bootstrap by launchctl[11630] for <private> failed (122: Path had bad ownership/permissions) 2025-03-22 22:49:19.507771 (gui/502 [100003]) <Notice>: exiting bootstrap mode

My Ownership/permissions for LaunchAgents
drwxr-xr-x 6 antiflash staff 192 Mar 22 22:49 LaunchAgents

My Ownership/permissions for plist
-rw-r--r-- 1 antiflash staff 842 Mar 22 22:49 homebrew.mxcl.syncthing.plist

Return for whoami commad
antiflash

Return for id command
uid=502(antiflash) gid=20(staff) groups=20(staff),12(everyone),61(localaccounts),79(_appserverusr),80(admin),81(_appserveradm),702(com.apple.sharepoint.group.2),33(_appstore),98(_lpadmin),100(_lpoperator),204(_developer),250(_analyticsusers),395(com.apple.access_ftp),398(com.apple.access_screensharing),399(com.apple.access_ssh),400(com.apple.access_remote_ae),701(com.apple.sharepoint.group.1)

As far as I can tell I have the correct ownership/permissions and id.

[SMillerDev]

Homebrew/homebrew-services#862

[antiflash1]

Great! Thanks you!!!!
This fixed the issue: https://bjango.com/help/istatmenus7/permissionshome/