When you reset your JumpCloud password or start using it to login to your mac for the first time, you need to let OS X know of the change. Keychain Access is the application used to keep track of your passwords and will prompt you with the following dialog after you login for the first time after the change:
When this happens:
- Click "Update Keychain Password"
- When asked for a login keychain password, enter the previous password you used to login. If you're not sure what this might be, try "insider".
DO NOT CHOOSE "Continue to Log In". If you do, you'll get popups that look like this:
To fix this issue, you need to update your existing login keychain.