Psychologists today are challenged as ethical decision makers by the ever-expanding development and use of digital technology in their own lives and in the lives of their clients. In this survey study, 256 doctoral-level U.S. psychologists rated their frequency of engagement in and ethical attitudes regarding four digital boundary crossings: advertising online, providing psychoeducation online, engaging in a digital nonsexual multiple relationship, and patient-targeted Googling. The study also examined six potential predictors of engagement and attitudes: therapist gender, therapist theoretical orientation, therapist years of professional clinical experience, client gender, the interaction of therapist gender and client gender, and digital status (i.e., therapists’ self-identification as digital natives or digital immigrants). Practice frequencies and ethicality ratings varied significantly depending on the boundary crossing considered. Significant predictors were identified for only one digital crossing: patient-targeted Googling. Therapist gender predicted the frequencies of patient-targeted Googling and hours of professional clinical experience predicted ethicality ratings. Professional implications, training recommendations for therapists, and directions for additional research are included. (PsycInfo Database Record (c) 2021 APA, all rights reserved)