Raman spectroscopy has long been considered a gold standard for optically based chemical identification, but has not been adopted in non-laboratory operational settings due to limited sensitivity and slow acquisition times. Ultraviolet (UV) Raman spectroscopy has the potential to address these challenges through the reduction of fluorescence from background materials and increased Raman scattering due to the shorter wavelength (relative to visible or near-infrared excitation) and resonant enhancement effects. However, the benefits of UV Raman must be evaluated against specific operational situations: the actual realized fluorescence reduction and Raman enhancement depend on the specific target materials, target morphology, and operational constraints. In this paper, the wavelength trade-space in UV Raman spectroscopy is evaluated for one specific application: checkpoint screening for trace explosive residues. The optimal UV wavelength is evaluated at 244, 266, and 355nm for realistic trace explosive and explosive-related compound (ERC) residues on common checkpoint materials: we perform semi-empirical analysis that includes the UV penetration depth of common explosive and ERCs, realistic explosive and ERC residue particle sizes, and the fluorescence signal of common checkpoint materials. We find that while generally lower UV wavelength provides superior performance, the benefits may be significantly reduced depending on the specific explosive and substrate. Further, logistical requirements (size, weight, power, and cost) likely limit the adoption of optimal wavelengths. Graphical abstract.