The SNSF project A World of Possibilities [WoPoss] aims at tracking the evolution of modal meanings in the diachrony of the Latin language. Passages expressing modal notions of ‘necessity’, ‘possibility’ and ‘volition’ are annotated following a pipeline that combines both automatic and fine-grained manual annotation. Texts are first gathered from different online open access resources to create the initial dataset. Owing to the heterogeneity of formats and encodings, the files are regularized before the implementation of the automatic annotation of linguistic features. They are then uploaded to the annotation platform [INCEpTION] which has been previously customized for the fine-grained manual annotation [Bermúdez Sabel, in press]. This second type of annotation is carried out following the WoPoss guidelines [Dell’Oro, 2019] and it also involves checking the automatic annotation for curation. In a third stage the files are automatically enriched with metadata. In this paper, we focus on the first two phases of the workflow – i.e. the gathering and automatic annotation of the texts and the fine-grained manual annotation –, which have been the core tasks of the WoPoss team in the first year of the project (2019-2020).