Several Roman period surface scatters and a settlement located in the Yambol District, along the Tundzha River, have been investigated within the last few years. Surface surveys and geophysical prospection were combined with a thorough material evaluation, to allow a description of the possible dimensions and character of several sites, all likely located in the territory of ancient Kabyle. The investigation focused on several single features located in the Tundzha Municipality, such as the extensive settlement near Kozarevo village and a smaller installation, perhaps a villa, near the Roman settlement at Kabyle. Several scatters, already detected by the Tundzha Regional Archaeological Project, were re-surveyed in Elhovo Municipality, between the Dereorman and Gerenska rivers. The territory along the two rivers seems to have been densely populated during the 2nd–4th c. AD, with about 11 scatters dated to the Roman period, likely representing small rural settlements, distributed in regular intervals along the two rivers. One of the settlements on the Dereorman River, Yurta-Stroyno, surveyed and excavated in 2014–2016, provided a comparative base for the rest of the area. Evaluating the gathered data, the territory of Kabyle seems to have been quite self-sufficient during the Roman period. The rural settlements provide evidence of raw material processing, production of everyday items, as well as a preference for the locally available products, such as household pottery, limiting the number of pottery imports to a minimum.