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As the Internet has grown, its user community has changed from a small tight-knit group of researchers to a loose gathering of people on a global network. The amazing and constantly growing numbers of machines and users ensures that untrustworthy individuals have full access to that network. High speed inter-machine communication and even higher speed computational processors have made the threats of system “crackers”, data theft, and data corruption very real. This paper outlines some of the problems of current password security by demonstrating the ease by which individual at counts may be broken. Various techniques used by crackers are outlined, and finally one solution to this point of system vulnerability, a proactive password checker, is documented.