Abstract New X-ray and optical observations shed light on the remarkable X-ray filament of the gamma-ray pulsar PSR J2030+4415. Images of the associated Hα bow shock’s evolution over the past decade compared with its velocity structure provide an improved kinematic distance of ∼0.5 kpc. These velocities also imply that the pulsar spin axis lies ∼15° from the proper motion axis, which is close to the plane of the sky. The multi-bubble shock structure indicates that the bow shock standoff was compressed to a small value ∼20–30 yr ago when the pulsar broke through the bow shock to its present bubble. This compression allowed multi-TeV pulsar e ± to escape to the external interstellar medium (ISM), lighting up an external magnetic field structure as the filament. The narrow filament indicates excellent initial confinement and the full 15′ (2.2 pc = 7 lt-yr) projected length of the filament indicates rapid e ± propagation to its end. Spectral variation along the filament suggests that the injected particle energy evolved during the breakthrough event.