The UAE, Saudi Arabia, and Qatar have recently been linked to a range of contentious exploits in the West. These include covert influence operations, espionage, and (in Saudi Arabia’s case) even acts of political violence. At first glance, such adversarial activity makes little sense, given longstanding economic, security, and ‘soft power’ ties. As this essay demonstrates, however, a potent mix of shared and state-specific motives has been steering these increasingly assertive monarchies—themselves experiencing intensive autocratization—into uncharted waters. Amidst serious divergences with the US, the European Union and other such partners, this has pitched Gulf-Western relations into a complex and unpredictable new era, with clear diplomatic and national-security ramifications as well as a pressing need for strengthened democratic defenses.