Online social networks (OSNs) such as Twitter and Facebook constitute an open space for developers to create sophisticated machines that imitate human users by automating their social network activities. The existence of socialbots is so powerful that bots can be transformed to inﬂuential users. Previous studies use fundamental functions such as posting a tweet or creating links to a speciﬁc target group to investigate the ability to inﬁltrate of these accounts. Our study analyzes the role of automated chatting in bots’ inﬁltration. Our analysis is compared with the state of the art of this kind and reveals that the chat functionally was able to improve Klout and follow ratio on about 24% and 123% respectively. Also, the advanced communications skills contribute to more message interactions between socialbots and other accounts. Based on our empirical experimental study the conversational socialbots inﬁltrate more successfully in the Twitter-sphere.