The response of massive caisson foundations to combined vertical (N), horizontal (Q) and moment (M) loading is investigated parametrically by a series of three-dimensional finite element analyses. The study considers foundations in cohesive soil, with due consideration to the caisson-soil contact interface conditions. The ultimate limit states are presented by failure envelopes in dimensionless and normalized forms and the effects of the embedment ratio, vertical load and interface friction on the bearing capacity are studied in detail. Particular emphasis is given on the physical and geometrical interpretation of the kinematic mechanisms that accompany failure, with respect to the loading ratio M/Q. Exploiting the numerical results, analytical expressions are derived for the capacities under pure horizontal, moment and vertical loading, for certain conditions. For the case of fully bonded interface conditions, comparison is given with upper bound limit equilibrium solutions based on Brinch Hansen theory for the ultimate lateral soil reaction. A generalized closed-form expression for the failure envelope in M-Q-N space is then proposed and validated for all cases examined. It is shown that the incremental displacement vector of the caisson at failure follows an associated flow rule, with respect to the envelope, irrespective of: (a) the caisson geometry, and (b) the interface conditions. A simplified geometrical explanation and physical interpretation of the associativity in M-Q load space is also provided. Finally, the derived failure envelope is validated against low (0.67. Hz) and high frequency (5. Hz) dynamic loading tests and the role of radiation damping on the response of the caisson at near failure conditions is unraveled.