Broken install after attempt upgrade to 7.0 and 7.1beta01 on macOS 15.4 - 'Too many levels of symbolic links'

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Tom

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Apr 22, 2025, 3:42:58 AM4/22/25
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Hi there, had issues when attempting upgrade. Got into a state where I could not launch it. Removing everything I could think of did not help.

 macOS 15.4 (24E248)

Steps I took:
  • Opened older version of Tunnelblick (version 6ish, not sure)
  • Accepted update offer to 7.0
  • Got message "The installation or repair took too long or failed. Try again?"
  • Trying again did nothing
  • Attempted to install 7.1beta01 instead
  • Got above installation failure message again, with "try again" still not working
  • Did several rounds of:
    • reboots, 
    • osascript uninstall command,
    • hard rm -rf's of /Library/Application Support/Tunnelblick, 
  • no improvement.
  • Only thing that worked was downgrading
  • installed v6.1beta1 with no issue.
I can give you full log if you really want, but there wasn't much interesting in it, other than the failure message. For each attempt, failure message was always:

2025-04-22 15:03:28.959725: listxattr() failed for '/Library/Application Support/Tunnelblick/Tunnelblick.app/Contents/Resources/openvpn/default'; error was 62 ('Too many levels of symbolic links')
2025-04-22 15:03:28.959762: Tunnelblick installer failed

The target of that symbolic link looked fine, and `cat /Library/Application Support/Tunnelblick/Tunnelblick.app/Contents/Resources/openvpn/default` lead to a bunch of binary output. I don't have the exact target anymore, that was several reboots ago, and I'm kinda loathe to attempt upgrade again.


Tunnelblick Developer

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Apr 22, 2025, 3:52:04 AM4/22/25
to tunnelblick-discuss
Thanks for posting the log.

This discussion should not be used to discuss this problem. Please discuss it at

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