<p>The piezocone penetration test (CPT<i>u</i>), combined with dissipation tests performed at various depths, is a widely employed in situ test for investigating the consolidation behavior of soils under varying drainage conditions. However, precise estimation of geotechnical parameters—particularly consolidation properties—from these tests involves two major challenges that require thorough consideration. The first challenge is the accurate determination of drainage conditions, while the second pertains to the interpretation of CPT<i>u</i>-derived dissipation curves. Soils with intermediate permeability, such as silty sands, often demonstrate partial drainage behavior, more complicating the analysis. Furthermore, non-standard dissipation curves frequently arise under such conditions, requiring the application of different methods to adjust and interpret these curves accurately. To address these challenges, this study utilizes finite element modeling coupled with an advanced hypoplastic constitutive model to numerically simulate the piezocone penetration process and associated dissipation tests in silty sands. The drainage regimes were delineated using the derived backbone characteristic curve. Subsequently, various types of non-standard dissipation curves were analyzed, and the factors influencing their development—including partially drained conditions, varying non-plastic silt contents, and differing dissipation depths—were systematically investigated. This research provides critical insights into the consolidation behavior of silty sands, thereby improving the reliability of geotechnical parameter estimation derived from CPT<i>u</i> and dissipation tests.</p>