Background: Pain is a common but understudied symptom among patients with heart failure (HF) transported by emergency medical services (EMS). The aims were to determine explanatory factors of a primary complaint of pain and pain severity, and characterize pain among patients with HF transported by EMS. Methods: Data from electronic health records of patients with HF transported by EMS within a midwestern United States county from 2009 to 2017 were analyzed. Descriptive statistics, χ 2 , analysis of variance, and logistic and multiple linear regression analyses were used. Results: The sample (N = 4663) was predominantly women (58.1%) with self-reported race as Black (57.7%). The mean age was 64.2 ± 14.3 years. Pain was the primary complaint in 22.2% of the sample, with an average pain score of 6.8 ± 3.1 out of 10. The most common pain complaint was chest pain (68.1%). Factors associated with a primary pain complaint were younger age (odds ratio [OR], 0.97; 95% confidence interval [CI], 0.96-0.97), history of myocardial infarction (OR, 1.96; 95% CI, 1.55-2.49), and absence of shortness of breath (OR, 0.67; 95% CI, 0.58-0.77). Factors associated with higher pain severity were younger age (b = −0.05, SE = 0.013), being a woman (b = 1.17, SE = 0.357), and White race (b = −1.11, SE = 0.349). Conclusions: Clinical and demographic factors need consideration in understanding pain in HF during EMS transport. Additional research is needed to examine these factors to improve pain management and reduce transports due to pain.