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A URL that points straight at an image file (Content-Type: image/*) has no HTML to scrape Open Graph tags from, so the fetch found nothing and the message showed no preview at all -- reported against https://imgs.xkcd.com/comics/creepy.png. link_preview_service now recognizes an allowed image content-type (same list storage.py uses for uploads) before falling through to the HTML/og: path, and returns the URL itself as the preview (LinkPreview.is_image). No need to download the body -- the already-SSRF-validated URL is the image. The frontend renders that case as a real expandable image (message-image + lightbox, same as an actual attachment) instead of the small title+description card, which would have nothing to show anyway. Verified end-to-end against the reported URL. Co-Authored-By: Claude Sonnet 5 <noreply@anthropic.com>