Objective: Web-based cognitive bias modification for interpretation (CBM-I) can improve interpretation biases and anxiety symptoms but faces high rates of dropout. This study tested the effectiveness of web-based CBM-I relative to an active psychoeducation condition and the addition of low-intensity telecoaching for a subset of CBM-I participants. Method: 1,234 anxious community adults (M_age = 35.09 years, 81.2% female, 72.1% white, 82.6% not Hispanic) were randomly assigned at Stage 1 of a sequential, multiple-assignment randomized trial to complete five weekly sessions of CBM-I or psychoeducation on our team’s public research website. After the first session, for Stage 2, an algorithm attempted to classify CBM-I participants as higher (vs. lower) risk for dropping out; those classified as higher risk were then randomly assigned to complete four brief weekly telecoaching check-ins (vs. no coaching). Results: As hypothesized (https://doi.org/j2xr; Daniel, Eberle, & Teachman, 2020), CBM-I significantly outperformed psychoeducation at improving positive and negative interpretation biases (Recognition Ratings, Brief Body Sensations Interpretation Questionnaire) and anxiety symptoms (Overall Anxiety Severity and Impairment Scale, Anxiety Scale from Depression Anxiety Stress Scales–Short Form), with smaller treatment gains remaining significant at 2-month follow-up. Unexpectedly, CBM-I had significantly worse treatment dropout outcomes than psychoeducation, and adding coaching (vs. no coaching) did not significantly improve efficacy or dropout outcomes (notably, many participants chose not to interact with their coach). Conclusions: Web-based CBM-I appears effective, but supplemental coaching may not mitigate the challenge of dropout.