Apologies. Yes, I was still having the issue as of maybe a few days ago and hadn’t heard anything on here at that point, so I went through my tech stack and did a little more troubleshooting.
I came to find out that the issue was related to my use of the Autooptimize Wordpress plugin for Wordpress, specifically inlining all of my CSS (which I’d done for page speed reasons). Turns out that it was pushing all of the tagging information way down on the page, and even though the tags were present and correct, the Twitter validator wasn’t picking them up.
Once I stopped inlining all of my CSS the issue cleared up.
This ticket can be marked as fixed.
Thanks