An imaging device includes an imaging unit, a recording medium, a communication unit, and a controller. In a case where an unsent piece of image data is present in the recording medium when the communication unit automatically establishes a new connection with a first external apparatus, when the first external apparatus is identical to an external apparatus having been connected with the communication unit at a time of generation of the unsent piece of the image data, of a plurality of external apparatuses, the controller allows the communication unit to automatically transfer the unsent piece of the image data to the first external apparatus. When the first external apparatus is different from the external apparatus having been connected with the communication unit at the time of generation of the unsent piece of the image data, the controller forbids the communication unit to automatically transfer the unsent piece of the image data to the first external apparatus.