Writing Skills are applicable to most areas of one’s life and career and helps people to stand out in their field. One can use these abilities to promote their business on social media platforms, blogs or any kind of marketing emails. Essays and their evaluation play a significant role in analyzing the capability of a person and will lay a path for the better learning process and overall development. Validating manually becomes a time consuming process and a burden on the validator. This paper describes the automated essay scoring application “Grammar Expert” which does the detection and correction of grammatical mistakes in the text received as input for the device and help in analyzing it according to one’s needs with the help of readability index. This work made use of Natural Language Toolkit (NLTK) for features extraction and Language Tool (LT) API for identifying errors. Storing the performance, results and feedback of each and every submission one did, is the thing which is not done before and plays an important role in understanding one’s area of mistakes and improve accordingly. It helps the validators in assessing their people through tests and by viewing or analyzing the stored performances, they may find the most common and vital mistakes and address among them. The most successful outcome is that it is user-friendly.