Substantial effort has been directed toward understanding complex associations between cannabis and pain, yet we have many, and sometimes conflicting, theories regarding cannabinoid analgesia. Although acute effects of cannabis on pain have received considerable attention, long-term effects remain understudied. Two studies were conducted. First, during the laboratory study, we measured pain ratings and pain tolerance in response to pressure-based mechanical pain among recreational cannabis users (n = 33) and cannabis non-users (n = 31). Linear mixed-effects models demonstrated that: (i) pain ratings (0-100 VAS) were not different between groups (B = 1.57 (95% CI: -10.84, 13.99), p = 0.801), (ii) pain tolerance (0-240 mmHg) was associated with anxiety (B = -5.33 (95% CI: -8.29, -2.33) p < 0.001), and (iii) users had lower tolerance after controlling for anxiety (B = -24.62 (95% CI: -49.32, 0.43), p = 0.046). Second, during the internet study, we retested these associations using more ecologically relevant endpoints in a separate sample. Participants completed the Graded Chronic Pain Scale, and pain-related daily interference was compared between users (n = 185) and non-users (n = 586). Linear models showed that interference (0-10 points) was associated with anxiety (B = 0.07 (95% CI: 0.06, 0.09), p < 0.001) and users reported greater interference after controlling for anxiety (B = 0.27 (95% CI: 0.09, 0.46), p = 0.003). Together, these outcomes suggest that regular cannabis use is associated with differences in pain processing, although additional studies are needed to provide enhanced mechanistic understanding.