The approach to teenage pregnancy has changed dramatically in the past years in areas of policy and education, however, stigmatization towards teenagers who are pregnant and/or parenting continues to be problematic, creating a wide range of challenges and increasing stress for these teens, their babies, and those supporting them. It is important for clinicians to understand the challenges these adolescents face to be better prepared to work and interact with them. Experienced clinicians that work with this population share insights on how to navigate the complex histories and current presentations of pregnant and parenting teens and how to recognize the affects of stigma in their lives, as well as offering treatment approaches that are helpful and effective in working with these adolescents.