This study fills a critical gap in International Relations (IR) scholarship by empirically testing an ancient, indigenous strategic framework derived from Kautilya’s Arthashastra, specifically the Four Upayas (Sama, Dama, Danda, Bheda). Moving beyond normative appeals for the inclusion of non-Western theories, the research rigorously operationalizes these classical strategies as observable, testable variables to provide a systematic explanation of India’s diplomatic choices. Using a structured, focused comparative case study methodology, the paper examines India’s foreign policy behavior towards two archetypal relational contexts: Bhutan (the Mitra or ally) and Pakistan (the Ari or enemy). It explicitly tests whether the Kautilyan framework offers superior explanatory and predictive power relative to Neoclassical Realism (NCR), a leading Western theory that integrates systemic and domestic variables. Findings underscore the continued relevance and distinctiveness of Kautilyan statecraft, revealing a relational and sequential logic that shapes India’s strategic toolkit, which is often obscured in dominant Western models. The paper contributes significantly to IR theory, strategic cultural studies, and practical foreign policy analysis by advocating greater methodological rigor in employing indigenous frameworks for understanding complex contemporary geopolitics.