A full scale experimental study has demonstrated that long, unrestrained pipeline dents typically experience fatigue cracking in the dent contact region and have significantly shorter fatigue lives compared to other dent types studied. Furthermore, these dents often fully reround under normal pipeline operating pressures, making them difficult to reliably detect and assess using existing depth-based approaches. Several conditions unique to the dent contact region accelerate fatigue damage accumulation and are considered in a case-specific long dent fatigue life prediction method. First, the contact region develops significant bending stresses that contribute to a higher rate of fatigue crack growth. Second, history dependent, thru-thickness residual bending stresses that may have a significant influence on fatigue behavior are present in the contact region as a result of plastic deformation associated with dent formation and subsequent rebounding. A method for predicting the fatigue life of long dents that accounts for these factors is presented here and is used to analyze specific cases for which laboratory data is available. Nonlinear finite element modelling of the dent life cycle, including the indentation and rebounding phases, is used to determine local stress range behaviors and residual stress distributions. The application of appropriate fracture mechanics based models of fatigue is discussed and demonstrated. Fatigue life predictions are made on a case by case basis for situations studied in the laboratory so that the validity and accuracy of the approach presented here may be studied.