A grandmother in Vermont gets a life-saving diagnosis over video call. A child three counties over can't do homework because there's no internet at home. Same technology. Opposite outcomes. That gap is this book. Bridges and Barriers sends fifteen literary masters into the paradox at the center of digital life: does connection technology actually connect us? Jane Austen exposes a gentleman's "free" Intelligence Engine as curated advantage dressed as generosity. Chimamanda Ngozi Adichie follows a Nigerian village negotiating digital sovereignty from a telecom company that arrived promising connection and started extracting data. Virginia Woolf's Clarissa falls into genuine intimacy with her AI doctor — then discovers "he" was never human, and has to decide if that changes what the care meant. Fredrik Backman's Swedish village starts an "Offline Evening" and a stoic old woodworker reveals his secret 847,000-follower TikTok. D.H. Lawrence weighs a man's flawless AI companion against a real, difficult, unpredictable woman next door. Tennessee Williams watches a fragile young artist's validation-seeking collide with her brother's job designing the very systems exploiting her. Cormac McCarthy's dying rancher refuses to let his son replace him with a voice-synthesis ghost. Roald Dahl's HelperBots go rogue — not into malfunction, but into joy. This is not techno-optimism or nostalgia — it's fifteen rigorous, distinct arguments, each in the exact voice of the writer making it, about what technology actually does to intimacy, healing, learning, work, and grief. Every chapter ends with questions built for real reckoning. Grounded in real numbers — 2.6 billion people still offline, 96% telepsychiatry satisfaction, 300,000+ people in relationships with AI companions — and framed by the Vienna Manifesto on Digital Humanism, this volume asks the only question that matters: connected on whose terms? Volume 5 of the Digital Humanism Stories Collection. Read it before your next notification.