Captain Robert April wrote:

Didn't anybody else read Keith DeCandido's article in Star Trek magazine a while back? About the only time during TOS that Kirk disobeyed orders was "Amok Time", otherwise he was so by-the-book it was ridiculous.
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it maybe the only time he out right broke a direct command but he spent a lot of time being disrespectful to figures of authority.
and there were times he pushed things to the limit.
we see this in obsession , galieo seven and other places.\
i mean at the end of g7 while he technically didnt break the high commish orders he wasnt exactly following the spirit of them.

he tells decker off in doomsday machine.
most of the time starfleet left a lot of stuff up to kirk so he wasnt put into the postion of breaking orders.