Despite the availability, capability, and inclination of older workers to remain in the workforce, research indicates that older workers are generally perceived and evaluated less favorably than younger workers (cf., Kite, Stockdale, Whitley, &Johnson, 2005). However, little is known about what factors lead older workers to be perceived less favorably. Up until this point, research investigating attitudes towards older workers has been limited to traditional work contexts. However, telework is an increasingly popular alternative work context and may be more appropriate for older workers. Another possible factor relating to evaluations of older workers is knowledge about age-related changes in ability. For example, the task demands of a job may be particularly high in fluid ability or crystallized ability. The work context and task demands of a job may be two potential sources of influence regarding perceptions of older workers. In the current set of studies, I examined the impact of applicant age, work context (telework and office work), and task demands (fluid ability and crystallized ability) on participants ratings of younger and older job applicants. In Study 1, a total of 16 job descriptions were selected based on their suitability and dependency on: office work/crystallized ability, office work/fluid ability, telework/crystallized ability, telework/fluid ability. Hiring managers recognized the jobs that were suited to telework or office work, but did not distinguish when either fluid or crystallized ability was of primary importance to a particular job. In Study 2, participants rated either younger or older applicants for 4 jobs selected from Study 1. The results of Study 2 were compelling. Older applicants were rated as more qualified when the job was dependent on crystallized ability, as well as when the job took place in a telework context. However, there were no significant differences between older and younger applicants when the job was dependent on fluid ability, or when the job took place in an office work context. The current research is critical to understanding the influence of task demands and the work context on differences between evaluations of older and younger workers.