This research monograph investigates the concept of "meaning" through an analysis of the term "connotation". Part 1 traces the history of "connotation" from its first documented use by William of Ockham in the 14th century, at which time philosophy and grammar were seen to complement each other, in the belief that the nature of things was reflected in grammar. Major changes in the meaning and usage of the term, which reflect the evolution of the concepts of meaning, are highlighted. Part 2 analyses the contemporary problems connected with the concept of "connotation" in linguistics, semiotics and literary criticism. It presents a discussion of the considerations involved in the analysis of meaning in natural language and stresses the need to avoid reductions that may impoverish the study of semiosis. Possibilities for dealing with "meaning" when it extends beyond the word or sentence into the area of textual analysis are presented.