Models of psychobiological stress reactivity have a foundation in the measurement of responses to standardized stress tasks. Tasks with anticipatory phases have been proposed as an effective method of stress induction, either as a stand-alone task or replacement constituent elements for existing stressor paradigms. Tasks utilizing singing as a primary stressor have been proposed but the efficacy of these tasks have not been demonstrated while maintaining adherence to a resting/reactivity/recovery framework desirable for heart rate variability (HRV) measurement. This study examines the viability of an anticipatory sing-a-song task as a method for inducing mental stress and examines the utility of the task with specific reference to measures of cardiovascular reactivity and recovery activity, and standard protocols to examine HRV reactivity and recovery. Participants completed a dual task with a math task and an anticipation of singing component. Responses were examined according to a resting/reactivity/recovery paradigm and the findings indicate that the sing-a-song stimulus is effective in generating a stress response. Significant differences in heart rate and self-reported stress between baseline and stressor conditions were detected, with greater magnitude differences between baseline and anticipatory phases. This study has demonstrated the viability of the anticipation of singing as a standardized stressor using cardiovascular measures and has described variants of this task that may be used for repeated measures study designs.