Since then I also discovered that Twiiter for IPhone behaves differently from desktop Twitter and also behaves differently in different Twitter accounts.
Here’s one example (of the many I noticed) On one account I can see a preview of the image that will display (if there’s also an image attached I can remove the link preview and the attached image then displays correctly) on 2 other accounts the link does not display a preview. Then you have no way of choosing which image should be displayed.
Of course, for people who retweet you, their RT automatically displays the shortened url image (from the Twitter card) instead of the attached image.
Hope the additional information helps!
Thank you!
Havi