Question: Does anyone know how long the war with the machines has actually been going on or what year it actually is in the real world?
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Answer: I don't think anybody knows - Morpheus says in the first film that the year is not 1999 as Neo thinks, but closer to 2199, but they don't know for sure. They just know the war started 'early in the 21st century' so presumably anywhere between 2000-2025.
Sam Johnson