The hospital grew organically over the centuries, absorbing almost half of the buildings around the piazza it shares with the cathedral of Siena. By the mid-fifteenth century, similar to other massive civic hospitals at the time, the Scala was a sprawling complex allowing for varying types of care that included treating the sick, housing foundling children, distributing alms, and sheltering pilgrims and travellers, all of whom had no grounding in the community or were unable to seek aid at home. This chapter investigates how the social condition of poverty shaped depictions of infirmity, taking as a case study the fifteenth-century frescoes painted in the pellegrinaio, or central male ward, of the hospital of Santa Maria della Scala. The pellegrinaio frescoes are dominated by architectural settings that have the same complexity as the narratives unfolding within them.