A multiple-fold automatic umbrella includes a penta-fold rope having its inner rope end secured with a locking head locked in a grip of a central shaft and defining a first rope section of the penta-fold rope from the locking head through an interior of the shaft to an upper guiding roller rotatably mounted in an upper portion of the shaft; a second rope section of the penta-fold rope from the upper guiding roller to a first lower guiding roller rotatably mounted on a lower runner slidably held in the shaft; a third rope section of the rope from the first lower guiding roller towards at least an uppermost guiding roller rotatably mounted in a top portion of the shaft; a fourth rope section from the uppermost guiding roller towards a second lower guiding roller rotatably mounted on the lower runner opposite to the first guiding roller; and a fifth rope section from the second lower guiding roller towards an outer rope end secured to an upper notch formed on the top of the shaft, thereby providing a rope dynamically balanced on opposite sides of the shaft for enhancing a smooth opening and closing operation of the umbrella.