Abstract: Cosmic voids, the largest observable structures in the universe characterized by a scarcity of galaxies, impact the Cosmic Microwave Background (CMB) through gravitational lensing, leaving a negative imprint on the CMB convergence (κ) map. This imprint offers insights into matter distribution within voids and the growth of cosmic structures. In addition, voids produce secondary CMB anisotropies via the Integrated Sachs-Wolfe (ISW) effect, manifesting as colder regions in the CMB and serving as probes of the Universe’s accelerated expansion. Motivated by debates on the ISW effect’s strength from voids and its potential link to the CMB Cold Spot, we explore the CMB lensing signatures of voids to test the ΛCDM model using N-body simulations. Using DES Year-1 data, we applied two void-finding algorithms—2D and VIDE—and a template fitting method with Gaussian-filtered κ maps, stacking CMB patches at void centers. Cross-correlation with DES Year-3 mass maps confirmed the consistency of our mass distributions. Furthermore, we cross-correlated Planck CMB κ maps with voids from DES Y3, covering ~4,200 deg², employing both the 2D void-finder and the new Voxel 3D void-finder. Applying optimal matched filtering based on MICE N-body simulations, we measured the lensing amplitude 𝐴κ = 1.03 ± 0.22 (4.6σ) for Voxel and 𝐴κ = 1.02 ± 0.17 (5.9σ) for 2D voids, aligning with ΛCDM predictions. Inverting the void-finding process to identify superclusters yielded 𝐴κ = 0.87 ± 0.15 (5.9σ). Our analysis indicates a good agreement with the consensus ΛCDM model with no weak or excess signals identified. We also show that Planck noise is the primary limitation, suggesting that future data from the Atacama Cosmology Telescope (ACT), Simons Observatory (SO), South Pole Telescope (SPT), and CMB-S4 will enhance sensitivity and enable more precise measurements.