The Cyber Kill Chain (CKC) is a prevalent concept in cyber defense; nevertheless, its emphasis on post-reconnaissance phases limits the capacity to foresee attacker activities outside the organizational boundary. This study introduces and empirically substantiates a pre-chain phase, referred to as contextual anticipation, which broadens the temporal framework of the CKC by methodically identifying subtle yet actionable signals prior to reconnaissance. The methodology combines the STEMPLES+ framework for socio-technical scanning with General Morphological Analysis (GMA), generating internally coherent scenarios that are translated into Indicators of Threats (IOT). These indicators connect contextual triggers to threshold-based monitoring activities and established courses of action, forming a reproducible and auditable relationship between foresight analysis and operational defense. The application of three illustrative cases—a banking merger, the distribution of a phishing kit in underground marketplaces, and wartime contribution scams—illustrated that contextual anticipation consistently provided quantifiable lead-time benefits varying from several days to six weeks. This proactive stance enabled measures such as registrar takedowns, targeted awareness campaigns, and anticipatory monitoring before distribution and exploitation. By formalizing CKC-0 as an integrated socio-technical phase, the research enhances cybersecurity practice by demonstrating how diffuse contextual drivers can be converted into organized, actionable mechanisms for proactive resilience.