Email is an important aspect of many e-learning methodologies. Often, it is the only medium through which students and teachers communicate in online education. Many teachers and students, however, are not trained in how to use email effectively or how to manage the interpersonal dynamics of the medium. Little research has been done to date to assess how people can better communicate via email. The qualitative study described here found out that contrary to popular notions about the brief and direct nature of email communication, politeness is an important and expected component of the language. It also revealed that many participants were uncertain about how to make their email polite according to the norms of the receiving culture. The study showed that different views on the nature of politeness in email can contribute to personal offence and online miscommunications. As a result, an instrument to assess politeness in email communication was designed (The Tool-Kit: An Instrument to Assess Politeness in Intercultural Email Communication). The instrument was developed as a way of dealing with the lack of common ground among email users to discuss and evaluate politeness in English email communication. This chapter describes in detail and with examples the different elements of the tool and shows how this instrument can provide a practical way of systematically assessing politeness in email communication. The tool also provides the necessary metalanguage necessary to reflect on the use of politeness indicators and provides clear guidelines to consider politeness protocols. As such, this innovative instrument promotes a practical approach for assessing politeness in email which could then assist the effective online interactions in e-learning methodologies. However, this tool is still in its infancy. Its limitations such as potential subjectivity and cultural bias are acknowledged and discussed in this chapter. Pedagogical applications of the instrument for online teaching to second language learners are also discussed.