This paper revisits the 1996 article Internet and Enterprise Strategy and assesses how its propositions were confirmed, transformed, or contradicted as digital connectivity evolved into an AI-enabled enterprise environment by 2026. The reassessment combines historical interpretation with a structured comparison of Internet-enabled capabilities, industry structure, value-chain transformation, platform intermediation, cybersecurity, data governance, artificial intelligence, and digital sovereignty. The analysis shows that the article correctly anticipated the strategic relevance of electronic markets, cybermediaries, transaction security, online communities, and internal rules for Internet use. However, the contemporary Internet exceeds the original framing: it is now a platformized, data-intensive, cloud-dependent, regulated, geopolitically contested, and increasingly AI-mediated environment. The paper argues that this progression from connectivity to AI-enabled enterprise systems does not replace Internet strategy; it extends it. For many firms, enterprise strategy is now enacted through digital infrastructures, algorithmic coordination, ecosystem participation, and governance capabilities.

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