FWIW, Simplecast recently went through a big change to a new 2.0 codebase. Lots changed. I did tell them recently that their stuff isn’t auto-embedding like they claim.
They say “Use this link to share via social media. It will automatically embed a player in WordPress, Medium, and many other popular sites.” with a link such as this: https://tgd.simplecast.com/episodes/dan-blackman-and-robyn-kanner-the-power-7fe152f4
It doesn’t work on Wordpress.com or self-hosted Wordpress. Let’s test it again now here on Meta:
Jumping in here! I migrated to the “new” simplecast in order to get the updated URL, like the one you posted from TGD, @codinghorror, but it still appears as a link rather than onebox
I fixed this bug. To give a little bit more of a context of what happened here:
Last time I worked on this I added some logic that was a little bit more complicated than needed because Simplecast has a bug, and unfortunately this workaround introduced a bug.
Usually, https://simplecast.com/oembed?url=URL should return a JSON with some information, but for specific links it does not work.