Computer mediated communication (CMC) is becoming increasingly prevalent and relied upon as the Internet facilitates the rapid growth of global networks and expands communication boarders. Today, many individuals rely on CMC for professional purposes, such as connecting long distance with co-workers to collaborate and advance workplace tasks. These individuals often rely on professional online collaborative programs that allow them to connect with colleagues across cities, provinces, and around the world. Relying on CMC for the transmittal of important electronic messages places it at the forefront for understanding how technical communication devices and networks function. This also requires an understanding of how ambiguity with online conversations can be decreased through the use of the Internet. However, what professional collaborative programs currently lack is a singular professional software that integrates both collaborative on-screen practices and online chatting capabilities with visual icons; or professional emoticons. The following research aims to investigate the communicative value of emoticons within a structured sentence via a study involving professional communication graduate students from Ryerson University and senior marketing communication professionals from a marketing agency in Toronto, Canada. Using concepts from critical visual methodology and a theoretical framework of visual semiotics, emoticons will be examined to see whether or not these pictorial symbols act in a similar fashion to punctuation symbols within a given sentence structure. The goal of this research was to investigate the use and meaning derived from emoticons in relation to grammatical punctuation for sentence structures in online communication environments. Specific emoticons were selected and used to measure participants‘ interpretation of each symbol within the particular context of a given sentence.