This chapter aims to extend the examination of seductive online user interactions, specifically when divergent hypermedia domains are presented for evaluation. In our earlier work, we recognized the need for researchers in the field of Human Computer Interaction (HCI) to consider seduction beyond what is popularly assumed of this phenomenon. Accordingly, the benefits we believe attainable when the concept of seduction is applied were highlighted. In this chapter we expand our initial ideas, by giving developers and researchers a practical insight into how the mechanics of hypermedia seduction currently may enhance and sustain the appeal of more engaging hypermedia products. A demonstration of our approach allows us to reveal the seductive strategies characteristic of an e-commerce website which delivers a more engaging user experience. In the second part of this chapter, we consider how our conceptual model may be utilized to evaluate more “extremist” hypermedia forms, specifically websites that are created and hosted on behalf of terrorist organizations. In our method, we consider the negative aspects of hypermedia seduction. We focus specifically on how certain factors may play an active role in influencing user behavior, by exploring the seductive strategies apparent in “extremist hypermedia”. At this stage, we are able provide some indications of the seductive means used by the developers and creators of websites in this genre. From an interdisciplinary perspective, we also provide researchers with a useful starting point towards understanding the mechanics of “extremist hypermedia seduction”. We anticipate that as knowledge about the nature of the interactions and communications of both the users and the creators of extremist websites improves, more suitable and effective methods for countering online extremism or terrorism may emerge.