When it comes to writing an email, a formal letter to a colleague, or even a text message to a friend, the ramifications of making a mistake while typing are insignificant. However, in the context of legal drafting, mistakes or typos, however small, can have significant financial consequences. In this Trial by podcast, we will explore three cases where this couldn't be more true, in fact, in one of the cases, a missing Oxford comma resulted in a US$5 million compensation payout.