In 1836 he sailed to the convict settlement at Hobart in Van Diemen's Land (now Tasmania) as private secretary to the Lieutenant-Governor Sir John Franklin. Here he wrote a report strongly critical of the state of "prison discipline". The convict system, being fixated on punishment alone, released back into society crushed, resentful and bitter expirees, in whom the spark of enterprise and hope was dead. Maconochie's report "can be said to mark the peak and incipient decline of transportation to Australia" when it was given to Lord Russell, the Home Secretary and ardent critic of transportation, claims Robert Hughes. Although this report was used by the Molesworth Committee on transportation in 1837–38, the criticism of this work forced Franklin to dismiss him.