The association of flash floods, or floods in general, with drought presents something of a paradox. The behavior of soil in contact with water and its variation with actual soil moisture has so far been relatively little scientifically investigated in the context of civil protection, crisis management, and flood protection. Therefore, there is a need to investigate the hydrophobic properties of soils under realistic conditions through testing, focusing on the potential for flooding. The paper analyzes to what extent drought can affect flood risk, how water infiltration into the soil takes place under different circumstances, and whether drought actually creates conditions that can increase the destructiveness of floods. The analysis was conducted by measuring water absorption into the soil throughout 2023 and then evaluating the results. The results of the testing highlight the need to monitor soil drought as part of the preparation for potential floods that may suddenly hit certain urban areas.