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Online grocery shopping (OGS) has significantly risen due to accelerated retail digitization and reshaped consumer shopping behaviors over the last years. Despite this trend, the German online grocery market lags behind its international counterparts. Notably, with almost half of the German population aged over 50 and the 55–64 age group emerging as the largest user segment in e-commerce, the over-50 demographic presents an attractive yet relatively overlooked audience for the expansion of the online grocery market. However, research on OGS behavior among German over-50s is scarce. This study addresses this gap, empirically investigating OGS adoption factors within this demographic through an online survey with 179 respondents. Our findings reveal that over a third of the over-50 demographic has embraced OGS, indicating a growing receptivity for OGS among the over-50s. Notably, home delivery, product variety, convenience, and curiosity emerged as primary drivers for OGS adoption among this demographic. Surprisingly, most adopters did not increase online grocery orders since 2020 and a not inconsiderable proportion have even stopped buying groceries online again. For potential OGS adopters, regional product availability turned out as a motivator, signaling substantial growth potential and providing online grocers with strategic opportunities to target this demographic. In light of our research, we offer practical suggestions to online grocery retailers, aiming to overcome barriers and capitalize on key drivers identified in our study for sustained growth in the over-50 market segment.