Accurate evaluation of undrained shear strength of soils is crucial in geotechnical design and assessment. In the practice, undrained shear strength is obtained most frequently from CPT data, dividing the net cone tip resistance by a cone factor, N_kt. For organic soils, values between 8.6 and 15.3 are reported, depending on the stress history. The cone factor can be conditioned to the results of laboratory tests, although uncertainties remain on the variety of stress paths followed by the soil elements around the tip of the cone, compared to the ones tested in the laboratory. Non-uniqueness in the definition of the cone factor may lead to either unsafe or over-conservative choices, partly undermining both the reliability and the sustainability of the design. This contribution analyses numerically the inversion technique used to determine the undrained shear strength of organic clays, exploiting data from an extensive in situ and laboratory investigation. The adopted constitutive model was calibrated on the results of laboratory tests. Cone penetration tests were simulated performing coupled hydro-mechanical numerical analyses via G-PFEM, developed in the last decade at CIMNE-UPC. The role played by initial stress state and previous stress history upon stress distribution at failure, cone factor and sleeve friction is discussed. The numerical results suggest how the sleeve friction could be used to condition the cone factor depending on the over-consolidation ratio and demonstrate how combining the different available CPT readings with the aid of numerical results may reduce the uncertainty in the estimation of undrained shear strength.