It has been a while since technology has brought the Internet close to people, offering access to information at one click. Search results are easily downloadable, allowing users to steal ideas from others. This conventionally breaks rules of academic integrity and gives way to an act known as plagiarism. Increased plagiarism has made various educational institutions search for originality checking. That is how big corporations developed numerous plagiarism detection software programs, some of which have become integral to the educational process. In the current article, we will try to understand what plagiarism is and how it is associated with academic writing assessment. Plagiarism is defined as an act of stealing someone’s ideas or words without acknowledging their owner. Despite two main types of plagiarism, prototypical and patchwriting, scholars argue that in academia, instructors normally face the unintentional one sourced in students’ poor understanding of academic writing norms and conventions. As a result, plagiarism detection software often fails to define true plagiarism, putting educators in a challenging situation when assessing the tasks. To overcome unfair task assessment, instructors should possess the ability to read and decipher plagiarism detection reports. This becomes possible when educators deliver courses on the leverage of plagiarism detection software. Additionally, educators are encouraged to reconsider the tasks and the assessment methods which currently seem outdated.