In shale testing, understanding the impact of effective stress and saturation conditions is crucial for accurate material behaviour assessment and parameter determination. In some cases, saturation in triaxial testing starts at low effective stress before ramping up for shearing. However, when in contact with water (or saline water), shales are prone to swelling, particularly at low effective stress levels, which can induce fissures and alter material properties. This study investigates the influence of fluid saturation strategies and stress/pressure variations on the mechanical behaviour of shales, particularly under low effective confinement. Building upon the comprehensive testing campaign (>140 tests) in Crisci et al. (2024), additional tests were conducted on Opalinus Clay shale, focusing on sample saturation methods and loading histories before shearing. The conditions under which tested specimens experience damage were detected through diagnostic indicators such as differences in stress path and lower strength and stiffness compared to intact specimens with identical basic properties. Micro CT scanning confirms that damage is related to the development of fissures. The volumetric changes in specimens were quantified throughout the testing phases and thresholds for tolerable strains and effective stresses, specific to this material, were established. Comparative analysis with Opalinus Clay from shallower depths and other shales globally revealed consistent findings. Notably, it is shown that, for all shale types analyzed, a linear failure envelope emerges in the low to intermediate effective stress regime when filtering out “damaged” specimens. This suggests that non-linear failure envelopes observed in some cases may stem from exposing specimens to low effective stress before shearing.