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This study explores aspects of journalistic quality in complex digital stories. Based on a tailored overview of the potentials of online journalism and digital long form stories for journalistic quality, all available award-winning stories of the subcategory Interactive of the World Press Photo’s Digital Storytelling Contest from 2011 to 2021 (n = 31) are examined according to their structure and journalistic quality criteria using Grounded Theory. The findings add to the long and ongoing research history in journalism and communication studies on the question of what journalistic quality entails and can be used as a basis for further analyses focusing on the technological and structural nature of digital stories and high-quality journalism. The analysis revealed a differentiation between linear stories and chapter stories with linear elements. While a multimedia nature, continuous text and video content prevailed in both forms, they differed in terms of their complexity as well as certain expressions of quality criteria. Gamification and immersion emerged as new yet debatable aspects of journalistic quality in digital stories.