Looking at today spam and phishing panorama, we are able to identify two diametrically opposed approaches. On the one hand we have general spam, which targets as much as people as possible with generic and pre-formed texts; on the other hand we have very specific emails, handcrafted to target high-value targets. While nowadays these two worlds don't intersect at all, 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 Spam (CTS), alongside with some workflows that exhibit how this all could be implemented. Furthermore, we suggest some preliminary directions that scientific community should consider to take, in order to address our concerns.