Information
Check to prompt the user to choose security settings if default settings fail; uncheck to automatically select. The recommended state for this setting is: Disabled.
Rationale:
Users may not have the necessary knowledge to make the best choices regarding Outlook security settings.
Solution
To implement the recommended configuration state, set the following Group Policy setting to Disabled.
User Configuration\Administrative Templates\Microsoft Outlook 2013\Security\Prompt User To Choose Security Settings If Default Settings Fail
Impact:
Enabling this setting will prevent a prompt from appearing when the default security settings fail. This should rarely be an issue since the settings are unlikely to fail in the first place.