Managing pain effectively is a cornerstone of quality end-of-life care, yet comprehensive population-level insights into its prevalence and determinants remain scarce. This study examined how often individuals experience significant pain near death and identified factors linked to greater pain burden. Using a retrospective, population-based design, we analyzed all Ontario residents who died between April 1, 2011, and March 31, 2015, and who completed a home care assessment within 30 days before death (n = 20,349). Severe daily pain was determined through linked provincial health databases and measured using a validated composite pain scale that captures both intensity and frequency, defining severe pain as pain of high intensity occurring daily. Severe daily pain was documented in 17.2% of decedents. Higher likelihood of severe pain was associated with being female, younger in age, and having greater functional limitations. Conversely, cognitive impairment was linked to a reduced probability of reporting pain. Patterns varied across disease trajectories—those dying from terminal conditions such as cancer reported more severe pain than individuals with frailty-related deaths (odds ratio = 1.66). While pain is a major concern for many nearing end of life, fewer than 20% experienced severe pain on a daily basis during their final month. Findings highlight the need for proactive, early palliative care engagement—particularly for subgroups at higher risk of distressing pain.