Good question. Here are a few random thoughts.
Prison reform, IMHO, has been going on fairly steadily in the English-speaking world since probably the end of the 19th century. The driving idea always seems to be that if we are somehow more "humane" with these people, they will indeed come to see the error of their ways and be rehabilitated. Believe it or not, the electric chair made its debut as a more "humane" way of executing people (Anybody here seen The Green Mile....??) so although the definition of the term has changed, the intent hasn't. My opinion on this is that it will probably yield some success for those very early in their criminal lives, or those who are not suffering from the more advanced form of anti-social personality disorder or psycopathy, like the Bernardos and Olsons mentioned earlier. For the latter, it has probably never worked and probably never will.
Second, I believe that there is an abiding (if somewhat naive) belief among most of us Canadians that people are all basically good, and will respond properly if dealt with from that premise. This, IMHO, is why we have difficulty dealing as strictly as we should with terrorists and their ilk, and why we get cold feet about things like Kosovo, OEF and OIF when it becomes necessary to whack/smack baddies.(Kosovo may be a bad example, as we led most of the Coalition non-US led air strike packages...) The epitome of this was the apocryphal story that when the events in Somalia were brought up in the House of Commons, one Hon Member stood up and righteously demanded to know why Canadian soldiers on a "peace-keeping" mission were carrying weapons. Once again, this fine and decent trait of ours runs smack into the reality of those who are simply not amenable to normal standards of behaviour, and for whom normal sanctions hold little or no fear.
Third, while I am reluctant to blame politicians for everything because it absolves us of responsibility, I have to say that IMHO the social inclinations and beliefs of many who seem to gravitate to the party currently in power are distinctly woolly. These people are more than likely to be found in the various echelons of the Public Service, including Corrections. I have commented before on these pages about my perception of a few years ago that there was a fairly significant divergence in views between the "front office suits" and the "uniforms" in CSC. In turn, they will apply what they believe to be "enlightened" methods, whether or not there is any empirical evidence to suggest that such measures will actually produce results. Further, I believe that these people would reject empirical evidence that "proved" that measures that they are uncomfortable with might actually be effective.
Just my take. Cheers.