diff --git a/apps/web/src/components/ChatMarkdown.tsx b/apps/web/src/components/ChatMarkdown.tsx
index 4c712365475d..c0225713ec4c 100644
--- a/apps/web/src/components/ChatMarkdown.tsx
+++ b/apps/web/src/components/ChatMarkdown.tsx
@@ -2943,6 +2943,7 @@ const CHAT_MARKDOWN_COMPONENTS = {
       : null;
     if (!fileLinkMeta) {
       const faviconHost = resolveExternalWebLinkHost(href);
+      const hasText = hastHasText(node);
       const pullRequestAutolink = String(
         (props as Record<string, unknown>)["data-pull-request-autolink"] ?? "",
       );
@@ -2974,6 +2975,7 @@ const CHAT_MARKDOWN_COMPONENTS = {
           {...props}
           className={cn(props.className, pullRequestAutolink === "commit" && "font-mono")}
           data-markdown-copy={pullRequestCopy}
+          data-markdown-image-link={!hasText || undefined}
           href={href}
           target={isSameDocumentLink ? undefined : "_blank"}
           rel={isSameDocumentLink ? undefined : "noopener noreferrer"}
@@ -3093,7 +3095,7 @@ const CHAT_MARKDOWN_COMPONENTS = {
             });
           }}
         >
-          {faviconHost && hastHasText(node) && !isPullRequestAutolink ? (
+          {faviconHost && hasText && !isPullRequestAutolink ? (
             <MarkdownExternalLinkContent host={faviconHost} plainText={plainHastText(node)}>
               {linkChildren}
             </MarkdownExternalLinkContent>
diff --git a/apps/web/src/index.css b/apps/web/src/index.css
index b59b8323f8a3..dfdf09af249d 100644
--- a/apps/web/src/index.css
+++ b/apps/web/src/index.css
@@ -1895,8 +1895,8 @@ code {
   color: var(--info-foreground);
 }
 
-.chat-markdown a:not(.chat-markdown-file-link):hover,
-.chat-markdown a:not(.chat-markdown-file-link):focus-visible {
+.chat-markdown a:not(.chat-markdown-file-link, [data-markdown-image-link]):hover,
+.chat-markdown a:not(.chat-markdown-file-link, [data-markdown-image-link]):focus-visible {
   background-image: radial-gradient(circle, currentcolor 0.75px, transparent 1px);
   background-position: left bottom;
   background-repeat: repeat-x;