The present study explores the chair and boat stereoisomers of Jet Propellant 10 (JP-10) fuel, exo-tetrahydrodicyclopentadiene (TCD), a high energy density hydrocarbon compound. Results from density functional theory (DFT) based quantum mechanical calculations indicate that JP-10 exo-chair isomer is more stable than the JP-10 exo-boat isomer by approximately 1.83 kcal/mol, in agreement with literature values . Flipping the triangular ∆C8C10C9 plane, the JP-10 exo-chair isomer (plane ∆C8C10C9 is under plane C1C2C4C3), through a transition state (TS) structure, where ∆C8C10C9 and C1C2C4C3 align into the same plane, becomes the JP-10 exoboat isomer (plane ∆C8C10C9 is above the plane C1C2C4C3), with an energy barrier is as high as 3.65 kcal/mol. All these three configurations, chair, TS and boat, possess the C2v point group symmetry whereas the intermediate structures which may not possess the same symmetry lie between them. Apart from related angle/dihedral angle variation, other geometric changes between the stable JP-10 chair and boat structures are small. Perhaps the noticeable electronic property changes are their dipole moments. The dipole moment of exo-JP-10-chair is given by 0.0156 Debye which is apparently smaller that the exo-JP-10-boat of 0.0426 Debye. The latter exhibits interactions of the protons on the flag carbon (C5) and boat tip carbon (C10).