One of the repercussions of the ever-rising popularity of knowledge management is a sudden increase in the number and range of knowledge management tools available on the software market. This can present a problem for organisations that are required to sift through the vast number of tools in the hope of finding one that meets their requirements. Moreover, guidelines describing how to go about selecting a commercial knowledge management tool do not currently exist. Therefore, the aim of this chapter is to present a set of guidelines to aid the evaluation and selection of a commercial knowledge management tool. In order to achieve this, a methodology is proposed that outlines factors and issues that could be taken into consideration during the selection of a knowledge management tool. Furthermore, an overview of criteria specific to knowledge management tools that can be used to evaluate and ascertain the features present in a knowledge management tool are also suggested.