The rapid growth of digital platforms has transformed the business models of micro, small, and medium enterprises (MSMEs), while simultaneously raising new challenges for Shariah compliance in daily transactions. This study aims to provide a critical diagnostic analysis of the gap between fiqh muamalah principles and contemporary digital MSME practices. This research employs a qualitative descriptive approach using semi-structured interviews, digital transaction observations, and documentation involving MSME actors and consumers. Shariah compliance is operationalised into four analytical dimensions: contract validity, transaction transparency, payment structure, and market behaviour ethics. The findings indicate that although MSME actors generally possess normative awareness of Islamic business values, Shariah compliance has not been systematically integrated into operational practices. Digital contracts tend to be implicit, product information transparency remains limited, and reliance on conventional digital payment instruments creates structural risks of riba. In addition, competitive pressure in digital markets encourages pragmatic marketing practices that potentially deviate from Islamic business ethics. This study contributes by offering a conceptual diagnostic framework to critically map the structural gaps between fiqh muamalah principles and contemporary digital MSME practices.
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