The establishment of an Aghlabid, then Fāṭimid-Kalbid dominion in Sicily had a deep impact not only on the island and on Mediterranean power constellations, but also on mainland Italy, especially in its Southern parts. Although the Peninsula was under continuous attack between the ninth and eleventh centuries, all attempts to place it under submission failed on a long-term basis. Examining three examples of ‘hindered passages’, this article proposes some new considerations about the question of this missed Muslim conquest. Besides the numerous raids, the establishment of many military bases and Christian-Muslim agreements on the mainland during the Aghlabid and Fāṭimid-Kalbid period points to a targeted politics of conquest. Furthermore, the fragmentation of Southern Italy, often claimed as the main cause for the ‘Saracen’ destructions, could, on the contrary, also be seen as the main obstacle to Muslim expansion due to its many fortified centres.