The chapter describes two prototype expert system applications to assist in the evaluation of dwelling fire safety though the methods used can be generalized to any building where life safety is a primary objective. The first, based on the philosophy of points schemes, demonstrates a system where the knowledge is elicited from expert opinion. The second illustrates an application where the rules are formulated on the basis of published guidelines and the exemplar relates to disabled users’ access and egress. The former displays a what-if potential for active/passive trade-off between different measures of fire safety while the latter offers an advice domain. The chapter includes a discussion on the choice of system and its implementation in each case.