The following two case reports discuss the effect of grief on their drug-use behaviour. Both case descriptions of substance use disorders are comorbid with depression and/or an anxiety-related disorder. Case 1 and 2 have a history of childhood sexual and physical abuse and report multiple drug relapses as a consequence of unresolved grief associated with the abuse. The maladaptive grief process of case 1 and 2 had presented itself in the subjective belief of having after death communications with the deceased. The application of cognitive behavioural techniques driven by psychodynamic insights, revealed a relationship between the grief experienced, childhood abuse and the use of prescription medication and illicit drug use. The case descriptions of grief are discussed in the context of substance misuse, mental health and the triggers associated with relapse in an attempt to further our understanding of substance abuse and therapy.