A dry bag is three parts working together: a coated or laminated fabric that blocks water, seams that join it, and a closure that seals the opening. The bag stops being a dry bag when any one of them fails, even if the rest still looks fine.
What wears those parts down is use and care, not the calendar. OutdoorGearLab, which reviews dry bags, says it knows many river users with Watershed bags that are still watertight after ten years of regular use, and notes that heavier materials hold up better than thin ones under heavy use. Cascade Designs, which makes SealLine bags, puts the care side simply: cleaning and maintaining a dry bag regularly can really help it last longer.
So a thin bag stored damp in a hot garage and a heavy bag rinsed, dried and stored indoors aren't on the same clock, even if you bought them the same day. If you're not sure whether a dry bag was ever fully waterproof in the first place, start with are dry bags actually waterproof?