Background: Boswellia serrata has traditionally been used in Ayurvedic medicine for its anti-inflammatory and antioxidant properties. Although several studies support clinical analgesic efficacy, the underlying mechanisms have not been investigated in human experimental pain models. This randomized, double-blind, placebo-controlled, crossover pilot trial aimed to examine the mode of action of Boswellia serrata to differentiate between its peripheral and central effects. This exploratory pilot study was designed to generate preliminary effect size estimates and assess functional pain-processing outcomes, rather than to provide definitive evidence of clinical efficacy. Methods: Twelve healthy volunteers were recruited and received either 300 mg of Boswellia serrata extract or a visually identical placebo twice daily for 28 days, separated by a 4-week washout period. Pain and sensitization were induced using a topical capsaicin model. Outcomes included spontaneous pain intensity, mechanical allodynia, pinprick hyperalgesia, thermal thresholds, and conditioned pain modulation, alongside psychological assessments of mood, anxiety, sleep, and structured adverse-event monitoring. Results: Results showed no significant difference in the primary endpoint of spontaneous pain intensity between Boswellia and placebo (VAS 43 ± 21 vs. 47 ± 17; d = 0.18; p = 0.539). Conclusions: While Boswellia serrata did not significantly reduce acute peak pain in this model, the observed trends suggest a potential multi-level modulatory influence on nociceptive processing and endogenous pain inhibition. These findings warrant larger clinical trials to further elucidate its therapeutic potential, particularly in populations with impaired pain modulation.