Cyndi Mitchell in a talk from Rails Conf points out how “enterprise” in the phrase “enterprise software” has taken on the opposite of its customary meaning.
If you call a person enterprising, you have in mind someone who takes risks and accomplishes things. And “Enterprise” has been the name numerous ships, real and fictional, based on the bold, adventurous overtones of the name. But Cyndi Mitchell says when she thinks about enterprise software, the first words that come to mind are bloatware, incompetence, and corruption. I wouldn’t go quite that far, but words like “bureaucratic” and “rigid” would certainly be on my list. In any case, “enterprise” has a completely different connotation in “enterprise software” than in “USS Enterprise.”