Research into the medieval Livonian archives today has to take into account a number of post-medieval events that took place on the territory of Livonia, due to which the original archives were dispersed, relocated, exported, and sometimes returned, but not always to their original location. As a result, any study into medieval archival documents produced in Livonia or pertaining to its history must begin with ascertaining the possible whereabouts of the documents. As the influential edition of the documents related to the Turaida Castle from the twelfth to the seventeenth century, compiled by Vija Stikane, demonstrates, these documents may be found in archives ranging from Poland (Warsaw and Krakow) through Sweden (Stockholm), Lithuania (Martynas Mažvydas National Library of Lithuania), Russia (St. Petersburg), not to mention private family archives in Germany. Many of these archives lack digital catalogues, and some of the documents are not catalogued at all. Only a small portion of medieval Livonian archives is preserved in the Latvian State Historical Archive, and access to it is limited due to the fact that very few of these documents are digitized, and the catalogue of the documents still remains in paper format and can be consulted only on the spot. In our paper, we consider the challenges posed by this situation in researching issues in medieval Livonian history, using as case study our own research into medieval illuminated charters issued in Livonia. One of the problems in locating the documents is that many of the charters were edited and published in the late nineteenth and early twentieth century, as part of the National Revival, and the whereabouts of the documents subsequently changed. However, these early editions are often partial and unreliable, because the selection of material and its interpretation was coloured by the national movement. In particular, locating and interpreting one of the earliest illuminated charters issued in Livonia, the 1248 charter of Nicolas, the fourth bishop of Riga, and its transumpt of 1424 posed a number of challenges. It was very hard to trace the earlier 1245 charter, apparently now in Stockholm Archive, by which Nicolas made the grant of land confirmed in the 1248 charter, of which an old photographic copy is preserved in the Riga School Museum. In addition, the transumpt of 1424 has been denounced by some early scholars as forgery, but this view was not supported by some contemporary scholars in Latvia. In our paper, we suggest some strategies that proved fruitful in our research into medieval Livonian charters, including ways in which we can critically assess and estimate the potentially lost materials. We also suggest that, given the current dispersed condition of the Livonian archives, the most fruitful approach would be to create a digital collective repository. This initiative, however, may face a number of administrative and institutional challenges, as well as being necessarily selective. In building such a digital archive, choices will have to be made which documents to digitize, with the oldest, the illuminated, or simply the most ornate documents being usually prioritized. Meanwhile, our experience shows that having access to “plain”, “inexpensive” charters is equally important to access the significance of the more carefully executed examples.