Looking at today phishing panorama, we are able to identify two diametrically opposed approaches. On the one hand, massive phishing targets as many people as possible with generic and preformed texts. On the other hand, spear phishing targets high-value victims with hand-crafted emails. While nowadays these two worlds partially intersect, we envision a future where Natural Language Generation (NLG) techniques will enable attackers to target populous communities with machine-tailored emails. In this paper, we introduce what we call Community Targeted Phishing (CTP), alongside with some workflows that exhibit how NLG techniques can craft such emails. Furthermore, we show how Advanced NLG techniques could provide phishers new powerful tools to bring upÂ to the surface new information from complex data-sets, and use such information to threaten victims’ private data.