Germany has not kept pace with the global development of online grocery shopping (OGS) and despite a pandemic-related increase remains on a moderate level. This phenomenon may reflect infrastructural benefits of stationary retailing, personal and household preferences, and perceptions of OGS services. To this end, this study investigates the determinants of OGS benefit perception addressing the interconnection between personal and household benefits and situational conditions based on qualitative data analysis. Data in three consumer lifestyle segments are gathered from a total of twelve German consumers. The study’s theoretical structure resorts to the theory of planned behavior (TPB) to cluster beliefs and to assess the impact of situational conditions. The study’s findings reveal large knowledge gaps and different individual preferences in service usage across the groups. We then reflect these preferences in the circumstances of the pandemic. We propose that retailers should increase advertising and consumer education efforts in some consumer segments while enhancing services transparency to consolidate consumers’ trust. On a mid-term level, further structural investments will be necessary to successfully compete in the future and serve a perspectively growing market.