Most existing research has viewed lonely employees as having limited control over workplace interactions, risking a self-reinforcing cycle of loneliness. In contrast, recent evidence suggest that factors such as self-compassion, self-efficacy, and a problem-solving mindset, can help break this cycle. To reconcile these divergent findings, we offer a balanced perspective on employees’ self-regulation of loneliness, considering both promotion and prevention strategies, as well as the role of leader-encouraged behaviors. Specifically, employees can reduce loneliness by employing promotion coping strategies—such as promotion-focused relational crafting and interpersonal organizational citizenship behavior (OCB)—when leaders encourage these approaches. Conversely, employees may remain lonely when they use prevention strategies, like prevention-focused relational crafting and interpersonal counterproductive work behavior (CWB), especially if leaders promote these strategies. We tested our hypotheses using multi-wave and multi-source data from 247 leader-employee dyads. The results show that employees’ workplace loneliness and leader-encouraged promotion strategies interact to influence promotion-focused relational crafting, which is negatively associated with subsequent loneliness through interpersonal OCB. Additionally, loneliness and leader-encouraged prevention strategies interact to influence prevention-focused relational crafting, which is positively associated with subsequent loneliness through interpersonal CWB. This study provides valuable insights into addressing the complexities of coping with workplace loneliness.