We sought to assess the proportion of Backwoods (Imperial Tobacco Group Brands LLC) cigar-related posts to Instagram that may contain misleading claims, nature-evoking imagery, and appealing flavors. Inclusion criteria for this study included an Instagram post with the hashtag “#backwoods” from 30 August to 12 September 2018. Rules were established to content analyze (n = 1206) posts. Categories included misleading packaging (i.e., the post contained an image of a Backwoods product with the descriptor “natural” on the packaging), misleading promo (i.e., the corresponding caption to the post contained hashtag(s) like “#natural”, “#authentic”, “#alwaystrue”), nature-evoking imagery (i.e., the post contained images of grass, water, and pastural views along with a Backwoods product), flavors (i.e., the post contained a Backwoods product with brand-specific flavors on the packaging), flavor promo (i.e., the corresponding caption to the post contained hashtag(s) of Backwoods’ brand-specific flavors), marijuana-related (i.e., the post contained an image of marijuana next to a Backwoods pack, rolled cigars visibly contained marijuana, or hollowed-out cigars next to marijuana), smoking (the post contained an image of smoke or a lit cigar), brand-specific promo (i.e., the post contained an image of a Backwoods t-shirt, sweatshirt, hat, etc.), and perceived gender. Among the posts analyzed, 645 (53.5%) were marijuana-related, 564 (46.8%) were flavors, 463 (38.4%) were misleading packaging, 335 (27.8%) were flavor promo, 309 (25.6%) were misleading promo, 188 (15.6%) were nature-evoking imagery, 165 (13.7%) were smoking, 157 (13.0%) were brand-specific promo, and 239 (19.8%) were perceived male gender. Backwoods cigar-related posts to Instagram often contained misleading images and promotions of a “natural” tobacco product, images of marijuana use (in the form of blunt-making), brand-specific flavors, smoking, and promotional merchandise. Misleading images and the depictions of marijuana use in addition to the variety of flavor options may increase product appeal to consumers. These results underscore the need for comprehensive regulation of cigar products similar to cigarettes.