Cloud Ceiling is a parameter describing the cloud used in meteorology. This parameter is related to the amount of the cloud and the cloud height at a specific location. From the cloud observations, the cloud ceiling can be derived. This study investigates the probability of cloud caused risk to aerial mapping, based on the historic record of the cloud observations. Because the cloud status could vary drastically from day to day, month to month, and year to year, it is very difficult, if not impossible, to predicate the cloud conditions. This study utilizes more than 10 years cloud observation for the statistical analysis. The observation from Magong airport located in Penghu is analyzed as a sample. It is demonstrated that the monthly statistics does provide information to the cloud caused risk assessment. However, the cloud ceilings are still difficult to predict, as observed from the yearly changes of monthly probability.