An electronic device with a touch-sensitive surface and display can execute a messaging application. The messaging application provides options for sending a message with a large attachment. In one option it allows for sending a message with a large attachment by uploading and storing the attachment on a cloud server, embeds a link to the storage location in the message, and sends the message without the attachment. The messaging application may also include a UI element in the message that includes an indicator about the status of the stored attachment. Furthermore, the messaging application may embed in the message a smaller sized version of the attachment before sending the message. The status indicator may display whether the link to the storage location has expired or whether the attachment has previously been retrieved from the cloud server.