Hi there! I understand you’re seeing repeated prompts for your keychain password when using Proton VPN on your Mac running OS X 10.14. Let’s work to resolve this so it stops interrupting your VPN experience.

First, just to clarify: When exactly do you see this prompt? Is it each time you connect to the VPN, at startup, or randomly? Also, do you use a specific way to unlock your Mac (password, Touch ID, etc.)?

In the meantime, here’s a step-by-step approach you can try, which is commonly effective for this kind of issue:

1. Verify Keychain Status
- Open the Keychain Access app (you can search for it using Spotlight with Cmd + Space).
- On the left sidebar, select the login keychain. Check if it’s locked; if yes, right-click it and choose Unlock Keychain 'login'.
- If it asks for a password here, enter your usual Mac user account password.

2. Ensure Your Login Keychain Password Matches Your User Account Password
Sometimes the login keychain password becomes out of sync with your Mac login password, causing the password prompts. You can update the keychain password if needed:
- In Keychain Access, from the menu select Edit > Change Password for Keychain “login”.
- Enter your old password and your current Mac user password.
- If you’re not sure about the old password, let me know and I can guide you further.

3. Grant Proton VPN Permanent Access to Keychain Items
The VPN client stores credentials in your keychain, so macOS may prompt for permission each time it tries to access them. To allow Proton VPN access without repeated prompts:
- Locate any Proton VPN entries in Keychain Access (look for items named ProtonVPN, ProtonVPN SSO, or similar).
- Double-click each entry, go to the Access Control tab, and select Allow all applications to access this item or specifically allow Proton VPN.
- Save and close.

4. Restart Your Mac to apply these changes.

If this doesn’t fully resolve it, sometimes resetting the keychain (backing up your passwords first!) or creating a new keychain solves stubborn prompts. Let me know if you want instructions on that.

Does this help, or do you continue to get the keychain password prompt? Feel free to share any error messages or behavior you notice—I’m here to help!