Poverty creates social conditions that increase the likelihood of homelessness. These include exposure to traumatic life experiences; social disadvantages such as poor educational experiences; being raised in a broken family, care homes or foster care; physical, emotional, and sexual abuse; and neglect at an early age. These conditions reduce people’s ability to negotiate through life challenges. This cross-sectional study documents the clustering and frequency of adverse social conditions among 152 homeless people from four cities in North West England between January and August 2020. Two-step cluster analysis showed that having parents with a criminal record, care history, and child neglect/abuse history was predictive of homelessness. The cluster of indicator variables among homeless people included sexual abuse (χ2 (N = 152) = 220.684, p < 0.001, Cramer’s V = 0.7), inappropriate sexual behaviour (χ2 (N = 152) = 207.737, p < 0.001, Cramer’s V = 0.7), emotional neglect (χ2 (N = 152) = 181.671, p < 0.001, Cramer’s V = 0.7), physical abuse by step-parent (χ2 (N = 152) = 195.882, p < 0.001, Cramer’s V = 0.8), and physical neglect (χ2 (N = 152) = 205.632, p < 0.001, Cramer’s V = 0.8). Poverty and homelessness are intertwined because of the high prevalence of poverty among the homeless. Poverty sets up a chain of interactions between social conditions that increase the likelihood of unfavourable outcomes: homelessness is at the end of the interaction chain. Interventions supporting families to rise out of poverty may also reduce entry into homelessness.