The U.S. Department of Veterans Affairs (VA) provides specialized intensive posttraumatic stress disorder (PTSD) programs to treat trauma-related symptoms in addition to providing service-connected disability to compensate veterans for injury sustained while serving in the military. Given the percentage of veterans who are receiving treatment for PTSD, in addition to seeking compensation for PTSD, a debate has emerged about the impact of compensation on symptom recovery. This study examined the associations among status of compensation, treatment expectations, military cohort, length of stay, and outcomes for 776 veterans who were enrolled in 5 VA residential PTSD programs between the years of 2005 and 2010. Mixed model longitudinal analyses, with age, gender, and baseline symptoms nested within treatment site in the model, found that treatment expectations were modestly predictive of treatment outcomes. Veterans seeking increased compensation reported marginally lower treatment expectations (d = .008), and did not experience poorer outcomes compared to veterans not seeking increased compensation with the effect of baseline symptoms partialled out. Veterans from the era of the Iraq and Afghanistan conflicts reported lower treatment expectations (d = .020) and slightly higher symptoms at intake (d = .021), but had outcomes at discharge equivalent to veterans from other eras with baseline symptoms partialled out. These findings help further inform the debate concerning disability benefits and symptom changes across time.