Rock mass characterization is crucial for estimating the strength of rock masses in rock engineering fields. Anisotropic rock mass characterization is essential for accurately assessing the strength and stability of rock masses, as it accounts for the directional variability in rock properties that can significantly impact underground structures. This study presents a new Anisotropic Rock Mass Characterization (ARMC) system to assess rock mass properties directionally and continuously. The ARMC system is organized into three categories: (i) Class A, representing intact rock; (ii) Class B, indicative of jointed rock mass; and (iii) Class C, accounting for boundary conditions. To evaluate the structural features of rock mass, this article introduces a new Geological Strength Index (GSI) called the Directional Geological Strength Index (DGSI). Additionally, the ARMC system includes two classification charts to enhance the understanding of rock masses: (a) Descriptive Quality Index and b) Classification Index of Degree of Anisotropy. The effectiveness of the ARMC system has been evaluated and compared with other classification systems, including RMR, RMR14, GSI, ARMR, and DRMR, under jointed rock mass. The comparison demonstrates that the inclusion and emphasis on DGSI features enhance the realistic, accurate, and directional characterization rating of rock masses.