When you share a post on Facebook, or when Jetpack Publicize publishes a post to your Facebook page, Facebook crawls the page and looks for Open Graph meta tags in the head to build a complete post preview (with an image, title, description, …).
Jetpack automatically creates these Open Graph Meta tags for you unless you already use another Open Graph plugin, in which case we let the other plugin handle things.
You can see what Facebook sees by entering one of your posts’ URLs in Facebook Debugger:
https://developers.facebook.com/tools/debug
Looking at the post you mentioned in the original post, it seems to include all the necessary tags, and Facebook doesn’t report any errors:
https://developers.facebook.com/tools/debug/og/object?q=http%3A%2F%2Fdiverticon.com%2Fcats-are-awesome%2F
I’m also able to share the post with an image today:
https://i.wpne.ws/cbm3
It appears that it was a temporary glitch on Facebook’s end.
If it keeps happening with other posts, do not hesitate to let me know!