There are disclosed devices, systems and methods for keyless courier entry into a safe using a courier mobile computing device for receiving and authenticating a courier login and a selection for keyless courier entry into the safe. The safe has a computing device for receiving and authenticating a selection for keyless courier entry into the safe. Upon receiving the authenticated selection for keyless entry, the safe computing device generates and displays a factor code based on a safe's serial number. The courier inputs the factor code into the mobile device. In response to receiving and authenticating of the factor code, the mobile computing device generates and displays a security check code. The courier enters the security check code into the safe computing device, which in response to the entry and upon authenticating the security check code, unlocks the safe.