This chapter problematizes the historicity of Paul and the communities addressed within Pauline letters and challenges the likelihood of the letters’ status as genuine correspondence. While scholarship assumes Pauline authorship of the “authentic” letters, other than biblical or biblical-like sources, there is no evidence of the historical Paul. That the historical Paul was active in the mid-first century is likewise a characterization found largely in Acts and Pauline letters. Similarly, there is a distinct lack of archaeological evidence of ancient Pauline communities. The chapter argues that internal references to communities in home settings within well-known regions are best assessed rhetorically rather than historically. With the letters read together as a collection, distantly spaced regions function effectively to signify the far-reaching spread of the message into prominent areas. The lack of extant evidence for and references to Pauline letters as unities, as one would expect in the case of genuine correspondence, casts doubt on their status as genuine correspondence. In addition, sightings of Pauline letters in later sources indicate a mid-second century date of the collection. These combined arguments add to the thesis that the letters were from the start pseudonymous and fictional.