If you arent logged in as an administrator, youre asked to enter an administrator name and password.

You might still be asked to log in manually after logging out, switching back from another user account, or locking your screen.

You might also see the message A user with an encrypted home folder cant log in automatically.

When changing the account password, you can choose not to use the iCloud password.

Or leave it selected, but choose a time interval from the pop-up menu.

If not, make one manually, (being sure to enter the whole thing as per the example above with the:8080 at the end).

Option-drag and drop these entries into your system keychain.

If your proxy server has more than one alias, or if you have several, then whenever you get a new unidentified dialog, repeat the above.

I have about 10 configs and it seemed like half couldnt retain the password and I would be prompted for it.

That created a new keychain entry and I no longer got prompted for the password.

The entry in the keychain itself gets deleted when the proxy usernamepassword resets.

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Mac Always Ask For Password For Internet