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Online Social Networks (OSNs) such as Twitter and Facebook have become a significant testing ground for Artificial Intelligence developers who build programs, known as socialbots, that imitate actual users by automating their social-network activities such as forming social links and posting content. Particularly, Twitter users have shown difficulties in distinguishing these socialbots from the human users in their social graphs. Frequently, legitimate users engage in conversations with socialbots. More impressively, socialbots are effective in acquiring human users as followers and exercising influence within them. While the success of socialbots is certainly a remarkable achievement for AI practitioners, their proliferation in the Twitter-sphere opens many possibilities for cybercrime. The proliferation of socialbots in the Twitter-sphere motivates us to assess the characteristics or strategies that make socialbots most likely to succeed. In this direction, we created 120 socialbot accounts in Twitter, which have a profile, follow other users, and generate tweets either by reposting messages that others have posted or by creating their own synthetic tweets. Then, we employ a 2k factorial design experiment in order to quantify the infiltration effectiveness of different socialbot strategies. Our analysis is the first of a kind, and reveals what strategies make socialbots successful in the Twitter-sphere.