Background: Personal contact between radiologists and their patients is scarce due to time constraints and logistical reasons which impacts on patient knowledgeability and satisfaction, but also on examination and diagnostic quality. Objective: We illuminate medical history interviews from a radiologist’s perspective and discuss its impact on the diagnostic quality. Based on these insights, we develop a digital medical interview assistant (DMIA) for radiology that is intended to collect information helping in improving radiological diagnostics. Methods: Conditions, issues, problems in the radiological examination process are assessed to collect requirements and to specify questions for a digital medical history interview. Results: A DMIA with conversational user interface is developed using the scripting language RiveScript. It is accessible through a social media messenger (Telegram messenger). An initial assessment of usability demonstrates a good usability. Conclusion: To overcome the information gap in radiology, a DMIA can simulate an assessment interview. It is still necessary to remove existing barriers in interaction with the DMIA for example by facilitating data entry options.