Abstract We have collected a new deep Chandra X-Ray Observatory exposure of PSR B2224+65 and the “Guitar Nebula,” mapping the complex X-ray structure. This is accompanied by a new Hubble Space Telescope (HST) Hα image of the head of the Guitar. Comparing the HST and Chandra structures in four epochs over 25 yr, we constrain the evolution of the TeV particles that light up the filament. Cross-field diffusion appears to be enhanced, likely by the injected particles, behind the filament’s sharp leading edge, explaining the filament width and its evolving surface brightness profile.