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This chapter discusses the goals of the project Retro-digitization and Interpretation of Croatian Grammar Books before Illyrism—RETROGRAM, the problems connected with them, and the lexicographic implications of the project. The goals of the project are to develop a model for retro-digitization of grammar books, create an open-access web portal with facsimiles of eight selected grammar books with their transcription or translation, compile a historical grammar and linguistic terminology index, and develop a thematic search tool. This chapter presents the project and its aims, and the grammar books and the challenges in digitization are described. The digitization process includes an annotation on the text level, terminological level, and morphological level using TEI tags. The challenges of the digitization process, starting with creating the TEI Header, are presented. The main challenge of the project is that the TEI module for grammar books has not yet been established. This project aims to offer a model for retro-digitization that will enable different search possibilities. The chapter describes the collaboration with the project Croatian linguistic terminology—Jena.