As offshore activities move into deeper ocean, conventional fixed-base platforms drastically increase in size and cost, One of alternatives available is a guyed tower, in which environmental loads are supported by guylines instead of structural members. The guying system of the guyed tower is designed on one hand to be stiff enough to limit the structural displacement in normal operations, but on the other hand to be soft enough to permit large slow sways during the presence of design-level storms. This compliancy provides an efficient means of withstanding harsh environment so that the disproportionate increase in size of deep water platforms can be kept to a rational limit. Novel configurations contain always some degrees of potential risks mainly due to the lack of experience. The most critical hazard inherent to a guyed tower may be the pullout of anchor piles. Once it happens, the guyline fails to function and it may eventually lead to the total collapse of the system. It is the aim of this paper to discuss and quantify the anchor-pullout risk of a guyed tower. A stochastic analysis is made for evaluating the first-upcrossing probability of the tension acting on anchor piles over the uplift capacity. Nonlinearities involved in the mooring stiffness and hydrodynamics are taken into account by using time-domain analysis. A simplified two dimensional dynamic model is developed to exemplify the underlying concept. Real hurricane data in the Gulf of Mexico spanning over 70 years are incorporated in a numerical example of which result clearly indicates highly potential risk of anchor pullout.