I’m not sure what you mean. Tweet media is about displaying media with sensitive content – I certainly don’t want to do that. I can’t find any other settings in Twitter that are to do with turning images on or off.
I don’t have any problem displaying photos on Twitter that I attach myself.
For the information of others with the same problem, I asked for help over at Twitter. They told me to submit one of my posts for validation through the Twitter Card validator. Once I did this and got approval back, my Twitter posts showed the preview.
I thought that WordPress had Twitter Cards validated by default, but it seems you need to get the validation yourself.
Hope this helps.
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