The Dragonfly nebula is a Vela-like Pulsar Wind Nebula (PWN) in the Cygnus region powered by the spin down of PSR J2021+3651. In X-rays, the inner nebula is a few arcseconds across, whereas at TeV energies VERITAS and HAWC has observed extended emission much larger than the extension in X-rays. The TeV gamma-ray source HAWC J2019+368 was originally discovered in 2007 by the Milagro Observatory and has been associated with this pulsar. Recent work has shown hints of energy dependent morphology for the source at TeV energies, supporting the interpretation of the gamma-ray emission being due to Inverse Compton scattering of electrons and positrons from interstellar radiation fields and cosmic microwave background photons. The hard spectral index and spectral softening above 30 TeV of the source are consistent with Klein-Nishina suppression of the electron-photon cross-section at high energies. We will present our most recent studies in modeling and analysis of HAWC J2019+368, explaining the X-ray and TeV emission up to the highest energies using the latest data from the HAWC Observatory.