In this article, some cases of historical document examinations by handwriting experts are presented: examination of an entry in Old Prussian from the 14th century, examination of a collection of proverbs from the 18th century, written in Lithuanian and German and the examination of the constitution of a monastery from the beginning of the 20th century. The author of the article shares her observations on when such examinations are possible, what challenges experts are facing and provides recommendations for the conduct of examination of historical documents.