Cryptococcal meningitis is a potentially devastating infectious complication of immunosuppression best characterized in individuals with HIV. Early recognition of and appropriate antifungal therapy for cryptococcal meningitis has a profound effect on outcomes, but with more varied presentations in well-resourced countries recognition may be delayed. We present four cases of cryptococcal meningitis in immunosuppressed patients, each with significant delays in diagnosis. Pulling from recollections of providers and the documented chart assessments, we discuss and tabulate the cognitive biases and diagnostic errors that contributed to delay. We further explore the knowledge deficits regarding cryptococcal meningitis that appeared in these cases. Once meningitis was considered, each of these cases of cryptococcal meningitis was rapidly diagnosed. Diagnostic delay was driven by knowledge deficits, followed by common biases such as availability heuristics and premature closing. These delays could be countered by maintaining broad differential diagnoses, re-evaluating the patient presentation after recognition of immunosuppression, and early consultation of specialists. Delay in diagnosis of cryptococcal meningitis is associated with high morbidity and mortality. By exploring the various case presentations and errors made, we hope to provide a counter to some of the knowledge deficits associated with cryptococcal meningitis, and to provide actionable advice for early consultation to infectious disease specialists in order to improve outcomes.