Multi-wavelength investigations of the interstellar environment around WR stars using IUE, IRAS, and optical data have led to the discovery of extended shells of gas and dust 50-100 pc in diameter in the lines of sight to the WR stars HD 50896, HD 96548, and HD 192163. These three stars share several common characteristics: (1) associated N- and He-enriched ring nebula, (2) spectral class WN5-8, and (3) spectral and photometric variability. Surveys of IUE spectra and IRAS images reveal a few additional candidates for such extended shells. Although positional coincidences cannot be excluded, possible origins of these extended shells include interstellar bubbles formed by stellar winds, non-conservative mass loss from binary systems, and supernova remnants. Current data suggest these three stars may be in a post X-ray binary stage, representing the second WR phase of massive binary star evolution. The discovery of extended shells of gas and dust possibly related to WR stars is important because the search for stars in the second WR phase, after the supernova of the primary, has been quite elusive. However, the observational evidence and available theoretical models for post-supernova massive binary star evolution and subsequent non-conservative mass transfer are not yet sufficient to firmly identify the origins of these extended shells.