In his “investigations” as in his fictional work, Nobel Prize laureate V.S. Naipaul has striven to seek out what in postcolonial enterprises has swung history, great or individual, from dream to nightmare. His penultimate novel, Half A Life, precisely describes the disintegration of a Portuguese colonial society on the Eastern coast of the African continent. While critics have mainly dealt with chapters located in India and England, we propose to analyze the last part of the novel, the one where the Indian protagonist discovers the complex world of the colony, an anachronistic world where the line of demarcation between colonists and natives becomes more and more clear to his eyes.