Terahertz (THz) imaging is a relatively new non-destructive analytical technique that is transitioning from established application research areas such as defense and biomedicine to studies of cultural heritage artifacts. Our research adopts a THz medical imaging system, originally designed for in vivo tissue hydration sensing, to acquire high contrast imagery of painted plaster samples in order to assess the ability of the system to image the Byzantine wall paintings at the Enkleistra of St. Neophytos in Paphos, Cyprus. The original 12th century paintings show evidence of later painting phases overlapping earlier iconography. A thin layer of lead white (2PbCO3·Pb(OH)2) underlies, in parts, later wall paintings, concealing the original painting scheme beneath. Traditional imaging modalities have been unable to image the underlying iconography due to a combination of absorption and scattering. We aim to use THz imaging and novel optical design to probe beyond the visible surface and perform in situ analysis of iconography beneath the lead white layer. Imaging results of painted plaster mock-ups covered with a thin layer of lead white and/or chalk, as well as of a painted wooden panel with obscured writing, are presented, and from these images sufficient contrast for feature identification is demonstrated. Preliminary results from the analysis of these mock-ups confirmed the utility of this technique and its potential to image concealed original paintings in the Enkleistra of St. Neophytos. The results encourage analysis of THz scattering within paint and plaster materials to further improve spatial resolution and penetration depth in THz imaging systems.