General Background Optimizing state revenue requires strict citizen compliance regarding calculation and reporting obligations. Specific Background Micro, small, and medium enterprises frequently exhibit low regulatory adherence due to limited understanding and readiness for modernized digital administration. Knowledge Gap Limited empirical research examines how socialization programs moderate the connection between internal awareness, procedural knowledge, Core Tax adoption, and regulatory adherence. Aims This study investigates how taxpayer awareness, Core Tax utilization, and tax knowledge predict compliance, evaluating tax socialization as a moderating variable among Krupuk micro-enterprises in Sidoarjo Regency. Results Structural Equation Modeling on 56 registered respondents reveals that awareness, system utilization, and knowledge significantly drive compliance. Furthermore, socialization strengthens the effects of awareness and knowledge but fails to moderate Core Tax utilization. Novelty This research demonstrates that while general socialization reinforces internal consciousness, it cannot independently bridge the technical competency barriers required for digital platform adoption. Implications Authorities must redesign outreach strategies to emphasize hands-on technical training, ensuring enterprise operators acquire practical skills for digital reporting. Highlights: • Internal taxpayer awareness significantly dictates administrative reporting consistency among rural micro-enterprises. • Practical understanding regarding tax regulations directly correlates with higher regulatory adherence. • Tax socialization campaigns fail to bridge the technical competency gap required for digital system utilization. Keywords: Taxpayer Awareness, Core Tax Utilization, Tax Knowledge, Tax Compliance, Tax Socialization