As victim organizations and users have become more cautious and aware of certain cyber attacks, cyber threat actors have developed new, creative methods to circumvent technical countermeasures and user vigilance. This chapter explores how attackers use deception strategies and techniques to skillfully circumvent human defenses. The chapter first looks at spear phishing, particularly through the lens of conjuring methods of misdirection and attention control. Later in the chapter the discussion turns to a burgeoning attack method—watering hole attacks, or strategic web compromises—which shifts the attack vector away from targeting victim communication platforms, particularly email, to compromising web servers. This section introduces the watering hole attack deception chain and examines attackers’ implementation of passive misdirection techniques and persuasive technology principles to deceive victims. The final section revisits and summarizes how certain deception techniques are used to initiate and perpetuate psychologically vectored cyber attacks.