Background/Objectives: α-lipoic acid (ALA) shows therapeutic potential but faces poor aqueous solubility (BCS Class II), gastric instability, and low oral bioavailability (~30%). This work investigated the formulation of cyclodextrin (CD) inclusion complexes of ALA to overcome the aforementioned limitations and improve nutraceutical applications. Methods: Phase solubility studies in simulated gastric and intestinal fluids screened for optimal CD, followed by molecular dynamics simulations and MM-PBSA binding free energy calculations. Inclusion complexes of choice were prepared by grinding, spray-drying, and lyophilization, followed by solid-state characterization (DSC/XRPD/FTIR). Further analysis was performed using pH-shift dissolution (USP II), permeability (PermeaPad^®, Caco-2), and (photo)stability according to ICH. Results: Hydroxypropyl-β-cyclodextrin (HPβCD) emerged as the optimal host due to favorable complexation, as confirmed by phase solubility studies and supported by molecular modeling, which revealed a favorable balance between inclusion complex stability and pH-triggered drug release. Formulations based on spray-dried and lyophilized HPβCD–ALA complexes (HPβALA-sd and HPβALA-lyo), in which ALA was fully amorphized, achieved near-complete dissolution within five minutes under biorelevant pH-shift conditions. This performance markedly exceeded that of free ALA (approximately 66% dissolution at pH 7.4) while maintaining moderate permeability (Papp 8–9 × 10⁻⁶ cm/s). Storage stability was enhanced markedly (88–90% ALA retention after 6 months at 40 °C/75% RH vs. 36% for free ALA) while UV stability was not improved through CD-complexation, probably due to interaction of UV-VIS light with the exposed portion of ALA. Conclusions: Even though the permeability of ALA–CD inclusion complexes remained medium (Papp ~ 8–9 × 10⁻⁶ cm/s) and unaffected by complexation, a significantly improved dissolution profile indicates better expected bioavailability compared to pure ALA.