Updating Keychain entry manually prevents next access from GUI tools afterwards: Always asks for permission I stumbled upon this using Tunnelblick and Viscosity. Adding a configuration to those VPN tools it is possible in the GUI during the first connect to specify user&amp;pass and save them in the keychain. The next connections will then use the saved credentials from keychain.

However if I change the password in the keychain using the security terminal command (add-generic-password -U-s-a-w) or via keychain access application, afterwards both Tunnelblick and Viscosity will show the "Permission to access keychain: [Allow, Allow always, cancel]"-dialog if I try connecting the next time. 

Is there any way to prevent this dialog? 


I looked a bit in the Tunnelblick source code, but couldn't find a check for "keychain tampering" or anything that could force this dialog from Tunnelblick's side.
If it is an configurable OS level protection?
For macOS Sierra:

To add an object and allow access (with user prompt), use the "-T Application" option. (Several applications can be used)

security add-generic-password -a "account" -s "name" -w 'password' -c aapl -T /Applications/Utilities/Keychain\ Access.app/Contents/MacOS/Keychain\ Access


Then to allow access without user prompt you need to modify the ACL for the object:

security -v set-generic-password-partition-list -s "name" -S "apple:"


The partition-list syntax is not very well documented. You might be able to see how Tunnelblick uses the ACL from the output of "security dump-keychain".

Source: man security