Inclusion Criteria:  Adolescents aged 16-17 years old Experiencing mild-moderate depression as indicated by a PHQ-8 score between 5-19, inclusive, assessed at screening/baseline Has regular access to a smartphone (Android or iOS smartphone with a recent supported operating system) with reliable WiFi access or sufficient data to engage with assigned study arm for the duration of the study Available and committed to engage with the program and complete assessments for an 8-week duration Able to read and write in English U.S. resident Regular, stable dose of antidepressant medications for (e.g. escitalopram/Lexapro, fluoxetine/ Prozac) for at least 60 days at screening with no plans to change medication/dose throughout the study If currently receiving psychotherapy, then must be in therapy for at least 4 weeks at screening with no changes planned for the duration of the study Participants must be able to understand and willing to provide informed assent and to comply with all study procedures and restrictions  Exclusion Criteria:  Lifetime diagnosis of a psychotic disorder, including schizophrenia and schizoaffective disorder Lifetime diagnosis of bipolar disorder Lifetime diagnosis of autistic spectrum disorder or pervasive developmental disorder (e.g. autism, Asperger syndrome, Rett's syndrome, or pervasive developmental disorder not otherwise specified) Suicidal attempt or ideation with a plan and intent to harm oneself during the last 12 months History of (a) drug and/or alcohol abuse within the past 12 months (determined by self-report) Current use of benzodiazepines (e.g. lorazepam, clonazepam, alprazolam, diazepam, triazolam) or certain sleep aids (zolpidem, eszopiclone, zaleplon) Previous Woebot Application use