How did a fledgling colony grow into current-day Sydney? Period One (1788–1850) begins with the First Fleet’s uninvited arrival and traverses food production challenges, including unfamiliar climate and landscape conditions and a lack of agricultural expertise. The early ‘hungry years’ were marked by food shortages and near-starvation, partly due to the imposition of British land management practices driven by diet preferences unsuited to local conditions. The initial focus on Sydney Cove’s sandstone lands and limited agricultural planning also hindered success. Rose Hill (Parramatta) and the fertile Hawkesbury-Nepean floodplains (centring on Green Hills/Windsor) became crucial agricultural lifelines, while expansion beyond the Blue Mountains opened access to farmland better suited to arable agriculture and pastoralism. By 1850, at the end of the period, the colony had grown from 1420 to 50,000, supported by various agricultural typologies regularly relying on convict labour, including mixed-farming estates, cropping, pastoralism and early agricultural infrastructures such as mills.