Schools attempting to engage with the families of all learners, including those with culturally and linguistically diverse backgrounds recognize the importance of oral and written communication that is written using understandable English. Using the basic principles of plain English coupled with speech act theory, this study began to investigate different aspects of text and functional intent. It examined exemplar pieces of written school generated communication, using different forms of linguistic analysis to determine whether the communication contained elements recognized to facilitate or impede the comprehensibility of each piece of communication. Additionally, a text assessment tool which can help schools to analyze the written text communication they send to families was developed and refined.