Medieval ars dictaminis or the art of correct letters writing represented one of key elements in medieval education. Although traditional correspondence takes a backseat today and is substituted by e-mails more and more, this skill is considered to be a part of the “equipment” that literates should possess even today. Topic of this paper is the comparison of medieval ars dictaminis handbooks with current manuals by comparing particular texts. Aim is to identify kinds of differences occurring in structure of medieval and nowadays handbooks, paper also focuses on changes of definition of letter during the time and how the role and function of letters in Middle Ages and today differs. Paper also considers how the rules of letter writing vary and how the approaches to ars dictaminis have changed over the time.