It's Not Just You: Tweet Previews Aren't Showing in iMessage Right Now
While sharing a Twitter link in an iMessage conversation typically results in a light-blue bubble with an in-line preview of the tweet, and an image if one was included, tweet previews appear to be broken right now.

As of Friday morning, Twitter links shared in iMessage conversations appear as basic gray bubbles with the twitter.com domain and no other information. It's unclear if this is an intentional change by Twitter to direct users towards its platforms, or if it is simply a bug. We've reached out to Twitter for comment and we'll provide an update if we hear back.
A similar issue with Instagram links in iMessage cropped up a few months ago, and it ended up being a bug that was fixed thereafter.
Earlier this week, Twitter rolled out support for larger image previews in the timeline in its iOS and Android apps, meaning that tall images will no longer be cropped into a 16:9 layout. Twitter is also rolling out a new Tip Jar feature that allows users to tip eligible accounts held by creators, journalists, experts, and non-profit organizations.
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