While gathering a collection of vintage book cover paintings for a special event in her quaint Rhode Island bookshop, Penelope discovers a spooky portrait of a beautiful woman, one who supposedly went mad, according to town gossip. Seymour, the local mailman, falls in love with the haunting image and buys the picture, refusing to part with it, even as fatal accidents befall those around it. Is the canvas cursed? Or is something more sinister at work?

For answers, Pen turns to an otherworldly source: Jack Shepard, PI. Back in the 1940s, Jack cracked a case of a killer cover artist, and (to Pen's relief) his spirit is willing to help her solve this mystery, even if he and his license did expire decades ago.