Multiple fires may break out simultaneously with or immediately after a large earthquake. They may result in a large urban fire. In particular, many firebrands may occur under strong wind conditions and disperse to distant places, thereby engendering spreading damage by leaping flames. Past records of large fires indicate that roofs are most likely to suffer damage from leaping flames. The probable reason is that roof tiles fall off and wood portions that constitute a roof are exposed just after a large earthquake. Therefore, this study made an aerial photography analysis on roof tile falling after the Kobe earthquake, and also conducted Fire Wind Tunnel experiments to investigate leaping flame damage on roofs with roof tile deficit.