The monument of Xana, a typical caravanserai, is located in the archeological site of the municipality of Traianoupolis, Evros, Greece and is one of the earliest khans in the Balkan area. Nowadays, the roof that once covered the monument and almost the entire first part that was used for travelers do not exist. The monument suffers by a vertical fracture on the northern wall, tensile cracks which run along the interior surface of the dome and vertical tensile cracks located at the openings of the western wall. Furthermore, hair cracks, loss of stone material, exfoliation and efflorescence worsen the pathology image of Xana.The target of the present study is the investigation of the monument's pathology by the use of nonlinear finite element analyses. A three-dimensional finite element model of the Xana's initial state is constructed. Soil-structure interaction effects are taken into account by the use of Winkler foundation. Various possible loading scenarios are investigated: (i) absence of wooden tendons; (ii) destruction of heavy roof; (iii) earthquake action; (iv) foundation settlement. The results of the nonlinear finite element analyses in terms of displacements and crack patterns can explain some of the main causes of the monument's pathology.