Financial cyberfraud and illicit trade have migrated from isolated schemes into structured digital ecosystems sustained by encrypted communication infrastructures. This dissertation examines how Telegram and darknet platforms function not merely as channels for criminal exchange, but as socio-technical environments that actively shape the communities facilitating cyber-enabled fraud. Rather than treating cyberfraud as a series of discrete offenses, this study conceptualizes it as an embedded system of coordinated actors operating within an underground network of communities building a whole, encrypted economy. Adopting a three-paper model grounded primarily in qualitative research methods, the dissertation analyzes (1) Russian-speaking fraud communities on Telegram, (2) differences between Telegram and darknet markets, and (3) underground pharmaceutical online trade as a case study of how cyberfraud infrastructures extend into offline public health risks. Drawing on longitudinal observations of over one hundred Telegram communities and darknet forums between 2021 and 2025, the research maps actor roles, trust formation practices, reputational systems, and retaliation processes. Theoretically, this dissertation refines criminological frameworks while demonstrating how their core assumptions are reconfigured within encrypted digital environments. It extends Routine Activity Theory by showing that capable guardianship in encrypted spaces is not simply absent but reorganized through endogenous governance mechanisms embedded within platform-based communities. It advances Rational Choice Theory by illustrating how decision-making in cyber-enabled illicit markets is not purely individual but shaped by platform affordances that structure perceptions of risk, trust, anonymity, and opportunity. In addition, drawing on Social Learning and subcultural perspectives, the dissertation reveals how shared communication signals and visible reinforcement practices normalize illicit participation and enable scalable knowledge transmission across hidden online communities. This dissertation argues that encrypted platforms actively restructure the organization, governance, and rationalization of cyber-enabled fraud creating the whole ecosystem. The term “ecosystem” is not used as a metaphorical descriptor but as a conceptual model referring to a structured, interdependent, and adaptive system of actors, platforms, and governance mechanisms that collectively sustain cyber-enabled fraud. Unlike fragmented platform-based analyses, the ecosystem framework captures how cyberfraud practices operate relationally across environments rather than within isolated spaces. It contributes to criminology and cybersecurity scholarship, providing empirically grounded understanding of how encrypted platforms restructure criminal opportunity and collective organization. Its ultimate goal is to offer a theoretically integrated and policy-relevant framework for advance comprehension of the resilience of contemporary cyberfraud and illicit trade within decentralized digital environments.