Dear Evan,
I had a suspicion that a plugin called “All in One WP Security” might be responsible for this behavior. Therefore, I did schedule a maintenance downtime and disabled that plugin to test again. Unfortunately that didn’t change anything!
I ‘ve also updated to the latest WordPress version (v.4.5.3) without any change.
Here are two screenshots taken one from the BackEnd where I put the image on the post announcement at the custom excerpt part and the other of what is actually shown in the Timeline frontend (aka. website).
BackEnd: https://imagebin.ca/v/2lsKtnfsMk0d
FrontEnd: https://imagebin.ca/v/2lsL9iuLmU5l
Any ideas? Can it be something that hasn’t been enabled on my WordPress settings??
Regards