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The Revolutionary War was the longest at about 8 years.

It is important to note that we have not actually been at war since 1945. Our Congress doesn't declare war any longer, though it is believed that they still do have the sole power to do so, according to the Constitution.

The longest military fighting would be the collective battles and massacres of the Native Americans, which started before our nation was a nation, and ended towards the end of the 19th century, which would have it at a century, at least.

The longest military fighting against a specific people in a consistent and enduring fashion was the Vietnam conflict at anywhere from 12 to 16 years depending upon how one classifies "hostilities" and "military involvement".

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