The aim of this study was to assess whether environmental enrichment and environmental conditions can influence the expression of sickness behaviour. The behaviour in response to injection of lipopolysaccharide or saline was examined in a total of 96 62-weeks old hatchmate hens kept in a free range or cage environment. There were eight experimental treatments, each with 12 birds. Half the birds were sourced from a commercial cage layer unit (C/-) and half from a commercial free range unit (FR/-). After intraperitoneal injection with either lipopolysaccharide or saline (as a control), the hens were placed in either a cage (-/C) or free range (-/FR) environment. Lipopolysaccharide caused greater suppression of activity in free range (FR/FR) than in caged hens, including less walking (53% reduction), roosting (-86%) and preening (-60%) (p < 0.05). Those responses were not observed in caged birds released into free range, nor in free range birds introduced to cages, suggesting that both the presence of and the familiarity with an environment affected sickness behaviour patterns. Increased sleeping was the most consistent response (+147%; p < 0.001), and it was least influenced by environment. It was concluded that free range layer hens can express a greater range of sickness behaviours than caged hens, and this may make it more difficult to recognise disease expression in the caged environment.