Community-based psychosocial support group (CB-PSS) interventions using task-shifting approaches are well suited to provide culturally appropriate services in low- and middle-income countries. However, contextual barriers and facilitators must be considered to tailor interventions effectively, particularly considering the challenges introduced by the COVID-19 pandemic. We explore the barriers, facilitators, and psychosocial changes associated with implementing a CB-PSS group intervention delivered by local lay providers to conflict-affected adults in Quibdó, Colombia, using both in-person and remote modalities. Data were analyzed from 25 individual interviews with participants and a focus group discussion involving staff members, including 7 community psychosocial agent facilitators and 2 mental health professional supervisors. The analysis used a thematic approach grounded in a descriptive phenomenology to explore the lived experiences of participants and staff members during implementation. Participant attendance in the in-person modality was compromised by factors such as competing work and family responsibilities and disruption caused by the COVID-19 pandemic. Participants in the remote modality faced challenges concerning unstable Internet connectivity, recurrent power outages caused by heavy rain, distractions, interruptions, and threats to confidentiality by family and coworkers. Despite these challenges, data revealed key contextual facilitators, including the community-based knowledge of facilitators and integration of traditional practices, such as the comadreo (informal talks and gatherings). Respondents shared that the CB-PSS groups promoted stronger community relationships and created opportunities for participants to exchange peer support, practice leadership skills, develop problem-solving skills based on peers’ experiences, and enhance emotional regulation skills. Differences and similarities across in-person and remote modalities are discussed, as are key considerations for practitioners and policymakers.