Chalk is a highly variable cemented biomicrite limestone that can show widely different rock strengths and patterns of micro to macro fissuring and jointing, due to variations in depositional environments and local geological histories. This paper describes the characterisation of a very weak to weak, low- to medium-density chalk through in situ profiling and laboratory testing, which provided new insights into the geomaterial’s mechanical behaviour. The chalk de-structures when taken to large strains, leading to remarkably high pore pressures beneath penetrating cones and degraded responses in full-displacement pressuremeter tests. Laboratory tests on carefully formed specimens explored the chalk’s unstable structure and marked time-, rate- and pressure dependency. A clear hierarchy was found between profiles of peak strength with depth from Brazilian tension, drained and undrained triaxial and direct simple shear tests conducted from in-situ stress conditions. Highly instrumented triaxial tests sheared from low confining stresses indicated stiffness anisotropy and showed very brittle failure behaviour from small strains. Progressively more ductile behaviour was seen as confining pressures were raised, with failures being delayed until increasingly large strains and finally stable critical states were attained. The chalk’s mainly sub-vertical jointing and micro-fissuring led to properties depending on specimen scale, with high-quality laboratory stiffness measurements significantly exceeding those obtained from in-situ geophysical testing, which far exceed the operational stiffnesses of the chalk mass. While compressive strength and stiffness appear relatively insensitive to effective stress levels, consolidation to higher pressures closes micro-fissures and reduces anisotropy. The results provided the basis for numerical analysis with advanced constitutive models that inform the interpretation of axial and lateral tests on driven piles and inform the development of new practical design methods.