The Spectacles wearable smart glasses device from Snapchat records snaps and videos for the Snapchat service. A Spectacles device can sync data with a paired smartphone and upload recorded content to a user’s online account. However, extracting and analyzing data from a Snapchat app is challenging due to the disappearing nature of the media. Very few commercial tools are available to obtain data from Snapchat apps. This chapter focuses on the extraction and analysis of artifacts from Snapchat and, specifically, Spectacles devices paired with Apple iPhones. A methodology is presented for forensically imaging Apple iPhones before and after critical points in the Spectacles and Snapchat pairing and syncing processes. The forensic images are examined to reveal the effects of each step of the pairing process. Several photos, videos, thumbnails and metadata files originating from Spectacles devices were obtained and tied to specific times, devices and locations. The research provides interesting insights into evidence collection from Spectacles devices paired with Apple iPhones.