Abstract Many older workers want to work longer. However, we understand little about the different workplace support needs they may have and whether workers choose to share their needs with others. The objective of this research was to qualitatively examine workplace disclosure-support decisions among workers aged 50 years and older. Sixty-eight participants from diverse employment sectors and with a range of personal experiences and circumstances (e.g., health conditions, caregiving responsibilities, job experiences) participated in 1 of 10 focus groups within the greater Toronto area. Recruitment drew on an existing cohort of Canadians from a survey research firm. Participants were asked about their work experiences, age-related changes, and disclosure decisions and experiences. Focus group discussions were audio-taped and transcribed. Qualitative content analysis was used analyze the data and identify emerging themes. There was variability in disclosure decisions with many participants being reluctant to share their needs at work. Four inter-related themes guided participants’ communication decisions: the need to communicate information; the desire to maintain one’s reputation; trust in others and perceived support; and perceived job insecurity. In discussing job insecurity, participants noted challenges in finding a new job, perceptions held by others of the cost-benefits of employing older workers, and labor market insecurity. The findings highlight challenges experienced by older adults in remaining employed and barriers to communicating their needs. Results underscore the importance of greater attention to ageism within organizations, the need for age-inclusive policies, and workplace flexibility to promote job sustainability across the life course.