Recent major blackouts all over the world have been a driving force to make power system reliability, regarding multiple contingencies, a subject of worldwide research. Within this context, it is important to investigate efficient methods of protecting the system against dependent and/or independent failures. In this sense, the incorporation of tighter security criteria in power systems operation and planning became crucial. Multiple contingencies are more common and dangerous than natural independent faults. The main reason for this lies in the complexity of the dynamic stability of power systems. In addition, the protection system, that operates in parallel to the supply system, is not free of failures. Thus, natural faults can cause subsequent contingencies (dependent on earlier contingencies) due to the malfunction of the protection mechanisms or the instability of the overall system. These facts drive the search for more stringent safety criteria, for example, n - K, where K can be greater than 2. In the present work, the main objective is to incorporate the joint generation and transmission general security criteria in power systems operation and planning models. Here, in addition to generators outages, network constraints and transmission lines failures are also accounted for. Such improvement leads to new computational challenges, for which we design efficient solution methodologies based on Benders decomposition. Regarding operation, two approaches are presented. The first one proposes a trilevel optimization model to decide the optimal scheduling of energy and reserve under an n - K security criterion. In such approach, the high dimensionality curse of considering network constraints as well as outages of generators and transmission assets is withstood by implicitly taking into account the set of possible contingencies. The second approach includes correlated nodal demand uncertainty in the same framework. Regarding transmission expansion planning, another trilevel optimization model is proposed to decide which transmission assets should be built within a set of candidates in order to meet an n - K security criterion, and, consequently, boost the power system reliability. Therefore, the main contributions of this work are the following: 1) trilevel models to consider general n - K security criteria in power systems operation and planning, 2) implicit consideration of the whole contingency set by means of an adjustable robust optimization approach, 3) co-optimization of energy and reserves for power systems operation, regarding network constraints and ensuring the deliverability of reserves in all considered post-contingency states, 4) efficient solution methodologies based on Benders decomposition that finitely converges to the global optimal solution, and 5) development of valid constraints to boost computational efficiency. Case studies highlight the effectiveness of the proposed methodologies in capturing the economic effect of nodal demand correlation on power system operation under an n - 1 security criterion, in reducing the computational effort to consider conventional n-1 and n-2 security criteria, and in considering security criteria tighter than n - 2, an intractable problem heretofore.