A transmission quality estimation system includes three or more nodes and a transmission quality estimation device configured to estimate transmission quality. A multi-core fiber having a plurality of cores, the multi-core fiber being used in at least a partial segment of a connection between the nodes. A node of the nodes includes a core connection unit configured to drop, add or relay light transmitted from, to or to each of to the plurality of cores of the multi-core fiber. The transmission quality estimation device includes an estimation unit configured to estimate transmission quality between the nodes on the basis of a transmission quality measurement light dropped by the core connection unit.
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