It is possible to attach the same media asset to multiple Direct Messages. However, you must get users’ express consent to set media as “shared,” and must provide them with clear notice that “shared” media will be viewable by anyone with the media’s URL. See the documented process below for how to set media to “shared.”
Did you set shared=true when you upload the image file in question?
Thank you for your response. I will give that a go for DMs. Thank you!
What I am most interested in however, is if the same media_id can be reused for multiple Tweet objects? Is this possible at all? I couldn’t find any documentation on the matter except for previous responses to threads which indicated it wasn’t possible. But I’ve been able to do it myself.