Explore how adversaries exploit trust boundary breakdowns between on-premises and cloud environments in this 48-minute conference talk from BSides Edmonton 2025. Discover the security challenges that emerge when organizations adopt hybrid cloud architectures, particularly the dangerous assumptions that Active Directory administrators often carry when extending into Microsoft Azure. Learn about the new attack surfaces introduced during cloud transitions, including misconfigured Conditional Access Policies, insecure Entra ID defaults, problematic Office integrations, and vulnerabilities in Privileged Identity Management (PIM). Understand how attackers leverage these blurred security lines to achieve lateral movement, maintain persistence, and escalate privileges across the hybrid infrastructure, moving seamlessly from Active Directory to Azure and Entra ID and back again. Gain insights into the illusion of clearly defined trust boundaries that often persists under a cloak of obscurity in modern hybrid environments, and learn to identify the hidden risks that can compromise organizational security across both on-premises and cloud infrastructures.