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Is it possible to print legends in a web map?
No, it is not possible to print legends in a web map. ArcGIS Online cannot print the Legend, North Arrow, and other map elements when printing a map using the Print task from the map viewer.
As an alternative, create a web application from the web map using the Classic Viewer (formerly known as Basic Viewer) application template. When printing from Classic Viewer, there is an option to add the legend to the map. For more details, refer to the following ArcGIS Online Help page, Create apps from maps.