In case you haven’t seen it yet, zf0 summer of hax was released in the last few days. While scanning through the content, I read a paragraph in the “Industry Check” section that perfectly sums up the state of computer security these days:
Are you professional types really this out of touch? I see all these papers about how to protect yourself from these super-fucking-advanced techniques and exploits that very few people can actually develop, and most hackers will NEVER USE. It's the simple stuff that works now, and will continue to work years into the future. Not only is it way easier to dev for simple mistakes, but they are easier to find and are more plentiful.
It is indeed much easier to look for a misconfiguration in the web app than to hack the actual web server software (be it apache, IIS or some other). It is much easier to guess the secret questions of a person and gain access to their account than it is to hack the actual service (be it web mail or something else). At the end of the day, people should be looking at security as an end-to-end picture, not just focus on parts of it. The tried and true “a chain is as strong as its weakest link” is in full force here.