In a controversial article published in 1972, Ephraim Kupfer challenged the prevailing image of the intellectual culture of late-medieval Ashkenazic Jews, who had in his view studied philosophical texts in a more widespread and systematic manner than previously acknowledged. Kupfer identified Menahem ben Jacob Shalem, also known as Menahem Agler, as one of the key figures engaged in the dissemination of philosophical knowledge in fifteenth-century Ashkenaz. Kupfer’s bold thesis has been widely challenged and criticised. However, the writings and manuscript glosses of Menahem Shalem, who was active in Prague in 1413 and corresponded with one of the leading halakhic authorities in the region, Abraham Klausner, have received comparatively scant attention so far. In this paper, I examine Menahem’s background and the surviving fragments of his oeuvre, his correspondence as well as his glosses on Maimonides’s Guide of the Perplexed and its commentary by Moses Narboni, and trace their reception and dissemination. By looking in detail at the reflection of attitudes and practices associated with the study of the Guide reflected in Shalem’s writings and glosses, I also attempt to contextualize Menahem’s interest in Maimonidean philosophy and offer a more nuanced appreciation of the role of philosophy in late-medieval Ashkenazic culture.