Poking around the web site for Law in Contemporary Society, a class taught this semester by Eben Moglen, (who is counsel for the Free Software Foundation and founder of the Software Freedom Law Center), i found Felix Cohen's Trancendental Nonsense and the Functional Approach, which (according to wikipedia) is one of "the most-cited law review articles ever written".
I haven't read the whole thing yet (and i'm neither a lawyer nor a philosopher) but it's fascinating reading. And from what i've read so far, it's a strong push toward directly addressing the values that lie hidden beneath our technical or mechanical decisions, and to avoid mistaking technical success or skill with a worthwhile outcome and clear goals at a societal level. This is something we software developers and system administrators struggle with as well (or at least i think we should). It's neat to get my head around these concepts from a different intellectual sphere, and a different era (74 years ago!) when the technical and mechanical tools i work with didn't exist in anything like their present form.
This kind of reading makes me wonder what works from Computer Science or Systems Engineering or Information Technology will have this kind of exhortative power and social relevance so far into the future. Do you have a favorite (or abhorred?) text from your field that offers the kind of moral and technical challenges that Cohen's work does?