When sending an MMS message with "new" content on a TF# (Toll Free number) or 10-DLC (Local area code), you MUST send the message and new content at least once before the content will appear in subsequent text messages. 

Why? The aggregator needs to cache the new content upstream. Once they generate a file for the new content they can reference that content on subsequent sends. 

This means that when the content is sent a 2nd time, the Image, Gif, Video or Audio File should display properly in the MMS message.