Surface active ionic liquids (SAILs), offer potential advantages for pharmaceutical applications. Given the low permeability of gabapentin, an antiepileptic drug, in the gastrointestinal tract as classified by the Biopharmaceutics Classification Systems (BCS), understanding the micellization behavior of SAILs is essential for developing effective drug delivery systems to improve gabapentin bioavailability. This study explores the micellization and thermophysical behavior of SAILs (2-hydroxyethyl)ammonium laurate [2-HEA][Lau], bis(2-hydroxyethyl)ammonium laurate [BHEA][Lau], and tris(2-hydroxyethyl)ammonium laurate [THEA][Lau] in the presence of aqueous gabapentin solution at varied temperatures through COSMO analysis, electrical conductivity and surface tension measurements. The electrical conductivity and surface tension measurements were employed to obtain the critical micelle concentration (CMC) and related thermophysical properties of binary (SAILs + water) and ternary (SAILs + water + gabapentin) systems at (298.15 to 318.15) K such as Π (interface surface pressure), σ_CMC (CMC point surface tension), A_min (minimum surface area occupied per molecule), Γ_max (Gibbs maximum excess surface concentration) have been computed. For better understanding the interactions between these components, Conductor like Screening Model (COSMO) was utilized. The study revealed that CMC values increased with temperature but decreased with increasing gabapentin concentration. Finally, interactions between SAILs and gabapentin were investigated through limiting molar conductivity Λ₀, and association constant K_A, determination.