The anisotropic fracture characteristics of oil shale are crucial in determining reservoir modification parameters and pyrolysis efficiency during in situ oil shale pyrolysis. Therefore, understanding the mechanisms through which temperature and bedding planes influence the fracture behavior of oil shale is vital for advancing the industrialization of in situ pyrolysis technology. In this study, scanning electron microscopy (SEM), CT scanning, and a real-time high-temperature rock fracture toughness testing system were utilized to investigate the spatiotemporal evolution of pores and fractures in oil shale across a temperature range of 20–600 °C, as well as the corresponding evolution of fracture behavior. The results revealed the following: (1) At ambient temperature, oil shale primarily contains inorganic pores and fractures, with sizes ranging from 50 to 140 nm. In the low-temperature range (20–200 °C), heating primarily causes the inward closure of inorganic pores and the expansion of inorganic fractures along bedding planes. In the medium-temperature range (200–400 °C), organic pores and fractures begin to form at around 300 °C, and after 400 °C, the number of organic fractures increases significantly, predominantly along bedding planes. In the high-temperature range (400–600 °C), the number, size, and connectivity of matrix pores and fractures increase markedly with rising temperature, and clay minerals exhibit adhesion, forming vesicle-like structures. (2) At room temperature, fracture toughness is highest in the Arrester direction (KIC-Arr), followed by the Divider direction (KIC-Div), and lowest in the Short-Transverse direction (KIC-Shor). As the temperature increases from 20 °C to 600 °C, both KIC-Arr and KIC-Div initially decrease before increasing, reaching their minimum values at 400 °C and 500 °C, respectively, while KIC-Shor decreases continuously as the temperature increases. (3) The energy required for prefabricated cracks to propagate to failure in all three directions reaches a minimum at 100 °C. Beyond 100 °C, the absorbed energy for crack propagation along the Divider and Short-Transverse directions continues to increase, whereas for cracks propagating in the Arrester direction, the absorbed energy exhibits a ‘W-shaped’ pattern, with troughs at 100 °C and 400 °C. These findings provide essential data for reservoir modification during in situ oil shale pyrolysis.