How literally should we take the promises attached to devotions like the scapular and the St. Gertrude prayer?
An emailer named Craig, skeptical of promises attached to devotional practices, asks how to understand claims such as the Rosary keeping one from heresy, the St. Gertrude prayer freeing a thousand souls from purgatory, and the brown scapular promise, in a Church full of sinners.
Answer
My general opinion is that we believe what is behind these promises until otherwise notified, because you want to give them as much leeway as possible, but you grow up as a Catholic with a healthy skepticism, because you know how legends and myths accumulate over the centuries. Most of the time there is a good dose of truth behind them, and then as the story is told down the generations it gets embellished and exaggerated, often innocently, as when St. Patrick's dealings with snakes become a legend, or the story of St. Lawrence on the gridiron saying 'turn me over.' Scripture itself notes myths and false beliefs that people held, like ideas about demon possession Jesus corrected. As for the specific promises, the St. Gertrude prayer or the St. Joseph prayer against drowning, I am no authority; to adjudicate them you would need impeccable source material about when the legend started and how it was embellished, so in that sense you are asking the wrong person. Theologians even debate how many Masses are needed to release a soul from purgatory, and you can never know the answer, which may tell you the answer is not that important. Nothing is wasted in the Catholic Church, including your prayers; if you pray for someone's salvation for thirty years and they refuse grace and die, you can ask heaven to transfer those prayers to someone else. So take the promises as given and believe them unless they are really extravagant, in which case apply a bigger dose of healthy skepticism, and let God take care of the numbers.