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The doctrine of double effect (DDE) is a principle of crucial importance in law and medicine. In medicine, the principle is generally accepted to apply in cases where the treatment necessary to relieve pain and physical suffering runs the risk of hastening the patient’s death. More controversially, it has also been used as a justification for withdrawal of treatment from living individuals and physician-assisted suicide. In this paper, I will critique the findings of the controversial Victorian Civil and Administrative Tribunal (VCAT) hearing Syme vs the Medical Board of Australia. In that hearing, Dr Rodney Syme, a urologist and euthanasia advocate, was defending his practice of prescribing barbiturates to terminally ill patients. Syme claimed that he prescribed the drugs with the intention of relieving their existential suffering and not to assist in suicide; he argued that the DDE could be applied. Pace VCAT, I argue that this is an illegitimate application of DDE. I argue that a close scrutiny of Syme’s actions reveals that, at the very least, he intended to give patients the option of suicide. He furthermore used what on a traditional definition of DDE would be considered a ‘bad’ means—the prescription of Nembutal—to achieve a ‘good’ end—the relief of suffering. The case demonstrates the crucial importance of analysing an agent’s ‘intention’ and the ‘effects’ of their actions when applying DDE. Ethicists and, indeed, the judiciary need to attend to the ethical complexities of DDE when they assess the applicability of DDE to end of life care. If they fail to do this, the doctrine risks losing its legitimacy as an ethical principle.