macOS prompts for password every time I turn on my VPN
Solution 1:
So I did some research, and the problem seems to occur with multiple VPN clients, third party or not. From what I understood the problem is that by activating the VPN, some settings e.g. the proxy settings are altered, and that is something the average user must not do without granting admin rights to the process. I found out two possible workarounds, but I can not guarantee that these will work.
- Try to reset your Keychain. Sometimes it gets messed up by multiple processes accessing it at the same time. Just make sure you have a backup of it. Then after the first start of your VPN connection, there should be a prompt again, but this time there should be the option to always allow access for this process. That should do the trick.
- You can manually edit which processes have access to the keychain. I don't have a Mac at hand to show you some screenshots, but if you can find out the name of the process demanding the access to the keychain, you can manually always allow it if the option mentioned in 1. does not show up.
I hope this helps, please give some feedback if it works, this seems to be a known problem without any advice given by Apple themselves. And maybe ask over on Ask Different, there are people with more knowledge of Apple devices than I have.
Some of the more interesting ressources:
Apple discussions: 1 2 3
Other 1 2