Coping skills cover an important area in rehabilitation counseling field. Bipolarity of coping skills as being adaptive or not adaptive has been prevalent throughout the literature. On the other hand, influence of contextual factors on coping skills has been underemphasized.  Recent researches indicate that contextual factors play major role in coping skills. This paper examines importance of contextual factors on coping skills particularly in relation to assessment issues in rehabilitation counseling area. After presentation of literature review regarding the topic, implications and recommendations for rehabilitation counselors were provided.