This mixed methods exploratory study examined how adult male prisoners serving sentences of life without parole adapt to the probability that they will be incarcerated for the remainder of their lives. As a second element, state prison wardens were surveyed about their support for the provision of certain amenities to those serving life without parole and the extent to which they believed those prisoners presented a risk of future dangerousness. Qualitative interviews were conducted with 24 inmates serving sentences of life without parole at a high security prison in Ohio. Informants identified factors that made adjustment more difficult or which enhanced the ability to adapt. Some study participants expressed hope that a favorable court decision or a change in sentencing laws would lead to release from prison. A survey sent to 430 state prison wardens asked if they supported providing prisoners serving life without parole amenities involving access to academic and vocational education programs, special housing assignments, and special programs to enhance adaptation. Wardens were asked to rate the extent to which they believed those prisoners presented a risk of future dangerousness. Study hypotheses were tested to determine if factors related to wardens’ prior work experience as a correction officer or in a treatment position, opinions about the primary purpose of prison, experience as a warden of a facility that housed prisoners serving life without parole, level of educational attainment, and gender impacted support for amenities and perception of future dangerousness. Three different two-way ANOVA tests were conducted, each of which had a categorical predictor variable and moderating independent variables of educational attainment and gender. Several of the main effects did reach the level of statistical significance. A reported belief that rehabilitation was the primary purpose of prison and level of educational attainment were significant in predicting wardens’ support for amenities. Having served as the warden of a prison at which inmates serving life without parole were housed and being female were found to be related to a lower perception of future dangerousness.