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According to attachment theory, one’s internal models of how one relates to others can bias the cognitive appraisals they make of themselves and others. These working models reflect a person’s attachment orientation and contribute to the stability and difficulty in shifting them, especially in adults. Furthermore, a person’s attachment style influences their capacity to regulate their emotions via their attachment system, by seeking actual or symbolic proximity to attachment figures. Individuals with insecure attachment orientations are more likely than secure individuals to use other strategies to regulate their emotions, which are often unhelpful and exacerbate distress. This thesis investigated whether long-standing cognitive biases related to attachment styles could be shifted using an interpretative bias training program, and whether shifting such biases influenced emotion regulation via the attachment system. Specifically, we examined whether cognitive bias modification techniques that target interpretive biases (CBM-I) could be adapted to target attachment biases. Study 1 found that a single-session of CBM-I was able to shift how individuals interpreted ambiguous attachment-related events. Studies 2 and 3 showed that interpretation changes remained one day following CBM-I training. In Study 3, imagery did not appear to enhance CBM-I. Studies 2 to 5 also examined the impact of CBM-I training on activation of the attachment system at both the conscious (Studies 2, 3, and 4) and preconscious (Study 5) level. Specially, Studies 2, 3, and 4 investigated emotion regulation following a distressing event and attachment prime. However, CBM-I did not appear to influence how individuals coped or utilised the attachment prime, even when variations such as an imagery induction (Study 3) and extended training (Study 4) were applied. Study 5 examined whether CBM-I influenced automatic mental accessibility to representations of attachment figures, and similarly did not find a significant impact of CBM-I. Overall, these findings demonstrated the capacity for CBM-I to shift interpretation biases that come about from long-standing internal working models. However, the extent to which this training impacts emotion regulation via the attachment system awaits further investigation. These findings provided preliminary evidence for therapeutic potential of CBM-I in shifting internal working models related to insecure attachment orientations.