It’s frustrating. I’ll paste a link in iMessage and hit “send” and I know it’s not gonna work correctly after a few seconds. Sure enough, the link sends without a preview.For me it doesn’t seem to work like ever. It will sit and spin after you send the link like it is trying to pull the preview, but it never shows up. And then I just permanently have the url line with the globe.
Then I just quit the Messages app, reopen it, hit “paste” again and it works perfectly.
So dumb.