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Introduction: Complexity in healthcare systems has been arbitrarily defined as tasks or systems ranging from complicated to intractable, with a general view of these not being 'simple'. Complexity in healthcare systems in first‐world countries has been well elucidated, however, data from third‐world countries is still scant. Materials and Methods: We present four cases each from three different organ systems—chronic kidney disease, alcohol use disorder, and heart failure—in the backdrop of our healthcare organization. We present our analysis of the complexities faced clinically and, in our local healthcare system which led to these events. Results: Analysis of these cases showed that patients with chronic kidney disease had vertebral–spinal pathologies due to poor infection control measures during haemodialysis. All these patients were young with a long history of secondary hypertension. In patients with alcohol use disorder, a common theme of how government regulations and peer pressure promote alcohol use is analysed. In the four patients with unexplained heart failure, vascular health is viewed as a fractal dimension and the various factors affecting vascular health are elaborated. Conclusion: Complexities exist clinically in making a diagnosis, and organizationally, in the variables and nodes dictating patient outcomes. Clinical complexities cannot be simplified but have to be navigated in an optimized way to improve clinical outcomes. [ABSTRACT FROM AUTHOR]