In one aspect, a disclosed portable authentication device (PAD) includes a processor, storage media, an interface for enabling communication with an external information handling system (IHS), e.g., a computer or a telephony device, and executable instructions embedded in the storage media, for automated authentication. The embedded instructions include instructions for enabling a user to store authentication information, e.g., use ID and password information, corresponding to an IHS destination, e.g., a telephone number of an interactive voice response system or an IP address of a web server. If the PAD recognizes the current destination, the PAD may respond to an assertion of a keypad control element by making authorization information corresponding to the current destination available to the user or providing the authorization information directly to the current destination. The PAD may include one or more telephony interface(s), e.g., RJ-11 jack(s) and one or more computer interfaces, e.g., USB connector(s).