Supernova remnant (SNR) G106.3+2.7, home to the Boomerang pulsar wind nebula (PWN), has long been thought to be a cosmic-ray PeVatron. However, its close proximity to the Boomerang PWN and the lack of gamma-ray (GR) observations above 30 TeV have made it difficult to model the nature of the emission mechanism. Recently, both the head (containing the PWN) and the tail (containing diffuse ejecta from the SN event) of the SNR have been separated by the MAGIC and Fermi-LAT observatories, giving us a glimpse into the very-high-energy (VHE) GR regime for both regions. With >6$\sigma$ detections for both the head and tail regions, the HAWC observatory is now able to extend these energy ranges past 50 TeV using new reconstruction algorithms on more than 2000 days of data. We present the multi-wavelength modeling of both the head and the tail regions, which supports a leptonic nature for the head and a lepto-hadronic nature for the tail, as well as possible sources for CR acceleration.