Avoid prompt after update of Tunnelblick.app is done: "Tunnelblick needs to Change ownership and permissions of the program to secure it"

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Gianluca Fadda

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Jan 2, 2026, 5:59:17 AM (10 days ago) Jan 2
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Good morning everyone,

I would like to ask if, after executed manually or via script the update of Tunnelblick.app is there a way to avoid the following message (via bash command):
Tunnelblick needs to Change ownership and permissions of the program to secure it

Screenshot 2026-01-02 at 11.58.12.png

Many thanks in advance and enjoy the new year :) 

Tunnelblick Developer

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Jan 2, 2026, 6:55:20 AM (10 days ago) Jan 2
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If you're using a script, see Command Line Installation of Tunnelblick and Configurations

That problem can be also caused by disabling Tunnelblick's background items, see Tunnelblick's Background Programs.

Gianluca Fadda

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Jan 7, 2026, 11:09:39 AM (5 days ago) Jan 7
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Hi,

Regrettably this did not work. When I scripted the upgrade to version 8.0, it will ask the prompt:
Screenshot 2026-01-07 at 17.07.03.png

In the screenshot above Tunnelblick Login item is already flagged and your guideline Command Line Installation of Tunnelblick and Configurations are about Tunnelblick profiles, but apparently not regarding update.

Could you please check and let us know which mechanic can allow to bypass the prompt after upgraded the Tunnelblick client?

Thanks a lot,

Gianluca Fadda

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Jan 7, 2026, 11:39:15 AM (5 days ago) Jan 7
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We would like to intercept and know which policy or MacOS internal prompt I currently see on the right side.

Doing that will allow to create one mobileconfig policy that I can also publish here.

Tunnelblick Developer

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Jan 7, 2026, 11:58:15 AM (5 days ago) Jan 7
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What are the contents of the script that updated Tunnelblick?

Tunnelblick Developer

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Jan 7, 2026, 12:00:29 PM (5 days ago) Jan 7
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And what exactly are you trying to do?

If you want to "update" Tunnelblick, you can just install the new version, via script or manually. Settings and configurations will be preserved.

Gianluca Fadda

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Jan 7, 2026, 12:21:40 PM (5 days ago) Jan 7
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Exactly updating Tunnelblick via bash custom script to version 8.0 (exploiting curl and the DMG from your source in order to download it, then mount It silently and then copying the .app file which replaces the old version of the .app (preserving also the existing config).

When I open the .app updated fo the first time, the prompt will ask to change permission for the first time. However I would like to automate even this step via mobileconfig policy, so that the prompt can be avoided.

Tunnelblick Developer

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Jan 7, 2026, 1:05:04 PM (5 days ago) Jan 7
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A script which copies it to /Applications won't work and will result in the problem you are having.

Instead, you need to use the "installer" program built into the new copy of Tunnelblick that you downloaded. See Command Line Installation of Tunnelblick and Configurations for instructions on how to do that (as I wrote earlier). 
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