Background: Androgen deprivation therapy remains the cornerstone of systemic treatment for advanced prostate cancer; however, progression to castration-resistant prostate cancer (CRPC) is almost inevitable. Contrary to traditional paradigms, supraphysiologic androgen exposure can suppress tumour growth in selected biological contexts, a phenomenon termed the “testosterone paradox.” Bipolar androgen therapy (BAT), which rapidly cycles between supraphysiologic and near-castrate testosterone levels, has emerged as a novel strategy to exploit adaptive androgen receptor (AR) dependence in CRPC. This review synthesises contemporary insights on BAT. Methods: A structured narrative literature search of Ovid MEDLINE and Embase (January 2009 - August 2025) was conducted to identify studies evaluating BAT in CRPC. Findings: Chronic androgen suppression promotes adaptive AR up-regulation, creating vulnerability to supraphysiologic androgen through AR saturation, transcriptional dysregulation, replication stress, DNA damage, senescence, metabolic reprogramming, and immune modulation. Clinically, BAT has been evaluated in multiple phase I–II studies and a randomised phase II trial (TRANSFORMER), collectively involving more than 250 men with CRPC. Across studies, BAT is feasible and generally safe in asymptomatic patients, produces PSA and radiographic responses in approximately 30%, improves health-related quality of life, and, critically, can restore sensitivity to subsequent AR pathway inhibition. Combination strategies with AR inhibitors, PARP inhibitors, immunotherapy, and other targeted agents are under active investigation, supported by emerging biomarker-driven hypotheses. International guidelines currently classify BAT as investigational, citing the absence of phase III survival data. Conclusions: BAT challenges conventional androgen suppression paradigms in CRPC. While current evidence supports its activity, safety, and sequencing potential, routine clinical adoption awaits confirmation from phase III trials.