An analysis method for the buckling process of a pipe section with a random pipelay imperfection is proposed. Four basic lateral modes, acquired by finite-element (FE) eigenvalue buckling analysis, are combined to provide the needed grid configurations for describing a real pipelay imperfection and an arc-length algorithm is used to analyze the snap-through process of the shell-element-grid model under nonlinear frictional boundary conditions. This paper also presents evaluation methods for the lateral buckling of two types of pipe-in-pipe systems that are used in the offshore oil and gas industry. For evaluating the buckling and postbuckling of compliant pipe-in-pipe systems FE analyses were carried out to judge the occurrence of the system buckling and furthermore to check postbuckling stresses induced in the buckles. The calculated results of the modified Riks algorithm indicate that only when high temperature would not trigger an abrupt short-wavelength buckle and when no yielding has been induced in the unavoidable long-wavelength buckles, the thermal stability and safety of compliant pipe-in-pipe systems can be proved. In the non-compliant pipe-in-pipe systems, firstly small-amplitude buckles of the carrier pipe may occur in the annulus between carrier pipe and casing pipe and the contact forces between the spacers and the casing pipe may drive the buckle of the pipe-in-pipe systems on the seabed. Based on the classical analytical solution of pipe buckling, four potential buckling modes corresponding to finite element models are developed to evaluate the stability and the postbuckling strength of such pipe-in-pipe systems.