In this article a discussion about counterinsurgency, foresight approaches and lone wolf challenge will be provided. Foresight can be defined as a component of strategic counterinsurgency operation with many benefits. Typically social settings of counterinsurgency operation are turbulent, complex and in some cases chaotic. Foresight should be linked to social practices of counterinsurgency agencies. In chaotic and emergent conditions, possibilities of foresight analyses are limited. This is why foresight analyses should be applied in such way that they enable proactive actions. Early warning systems and foresight diagnoses, prognoses and prescriptions should serve directly expected phases of counterinsurgency operations (pre-operation phase, operation phase and phase after counterinsurgency operation). If stakeholders want to develop effective early warning systems in relation to lone wolf challenge, it requires updated information of psychological and sociological behavior patterns of potential lone wolves. Early warning systems (and also weak signal systems) should be tailored to identify and recognize alarming psychological and social signals of potential lone wolf activities. In general, mass counterinsurgency attacks are problematic because larger trauma behavior (with terror behavior) can be expected to happen. In this conceptual study, alternative eight patterns of lone-wolf terrorism will be presented. These identified patterns are based on morphological analysis. To understand lone wolf phenomenon, we need more empirical research about these alternative psychological and sociocognitive patterns. Concerning terror intelligence challenges, we can note that probably the pattern where terror attack is solo, non-directional and not ideologically motivated is the most challenging pattern of lone world terror phenomenon. On the other hand, the social pattern where terror attack is not solo, and it is directional, clearly rationally motivated and also ideologically motivated is the easiest lone wolf pattern to be observed before the attack happens. If we are able to contextualize the lone wolf phenomenon and identify facilitation channels and causal qualities of lone wolf behavior, it is possible to development effective counter operations of lone wolf terror. Other social patterns of lone wolf terror are more or less complex issues to be observed beforehand. Understanding lone wolf terror and explaining causal and complex relationships of lone wolf phenomenon need more research in the future. Especially supportive incentive mechanisms of lone wolf terror (ideological support, operational support and psychological support) need more scientific attention. Issues of anti-fragility, resilience, flexibility, adaptability, artificial intelligence support, and weak signal sensors are going to be critical challenges in the global battle against lone wolf terrorism.