In this paper, a new reliability-based risk-involved model is presented for multi-period macrogrid expansion planning (MAGEP) by amalgamating the notion of community microgrids (CoMigs) within a market environment. The main targets of the proposed model are not only to develop a holistic framework for the MAGEP problem, but also to scrutinize the impacts of the macrogrid-connected multi-CoMigs on power supply reliability enhancement.To that end, the mathematical formulation of the proposed model falls into a nonconvex mixed-integer nonlinear three-level optimization problem. The lower-level outlines a security-constrained bid-based-pool electricity market aimed at providing an efficient platform for different CoMigs and market participants-generation companies (GenCos) and distribution companies (DisCos)-to freely trade electrical power across the macrogrid. The intermediate-level represents an interactive decentralized multi-period twostage microgrid expansion planning (MIGEP) problem in which optimal expansion plans of the CoMigs obtained in the first stage will be examined against the reliability restrictions in the second stage. The upper-level, however, addresses a centralized multi-period techno-economic MAGEP problem, while handling the risks of planning arising from severe uncertainties in forecasted price, demand, and power generation of the CoMigs through a potent envelope-bound information-gap decision theory (IGDT). Due to its proper tackling of the non-convex mixed-integer nonlinear multi-level optimization problems, the symphony orchestra search algorithm (SOSA) is widely employed for solving the proposed model. Effectiveness and capability of the newly developed model are numerically analyzed and verified using its implementation on the IEEE 30-bus and IEEE 118-bus test systems. K E Y W O R D S community microgrids (CoMigs), envelope-bound information-gap decision theory (IGDT), macrogrid expansion planning (MAGEP), microgrid expansion planning (MIGEP), reliability