diff --git a/components/selection-toolbar/shared.tsx b/components/selection-toolbar/shared.tsx
index b6b0fefc..e806d4f6 100644
--- a/components/selection-toolbar/shared.tsx
+++ b/components/selection-toolbar/shared.tsx
@@ -103,29 +103,56 @@ export function useCopyFeedback() {
 
   const copy = useCallback(async (text: string) => {
     let success = false;
-    const finalText = await shortenHighlightUrlsIn(text);
 
-    try {
-      await navigator.clipboard.writeText(finalText);
-      success = true;
-    } catch {
-      // Fallback for iOS Safari and older browsers
-      const ta = document.createElement("textarea");
-      ta.value = finalText;
-      ta.style.position = "fixed";
-      ta.style.top = "0";
-      ta.style.left = "0";
-      ta.style.opacity = "0";
-      document.body.appendChild(ta);
-      ta.focus();
-      ta.select();
+    // Why we don't just `await shortenHighlightUrlsIn(text)` first: the URL
+    // shortening is a network round-trip, and awaiting it consumes the
+    // transient user activation that navigator.clipboard needs. The write
+    // would then silently fail on the *first* click and only succeed on the
+    // second (when the short link is cached and the shorten resolves
+    // synchronously). Instead we hand the clipboard a *Promise* of the text
+    // via ClipboardItem — the browser keeps the gesture alive while the
+    // async work finishes, so a single click copies the shortened URL.
+    if (typeof ClipboardItem !== "undefined" && navigator.clipboard?.write) {
       try {
-        document.execCommand("copy");
+        const item = new ClipboardItem({
+          "text/plain": shortenHighlightUrlsIn(text).then(
+            (s) => new Blob([s], { type: "text/plain" }),
+          ),
+        });
+        await navigator.clipboard.write([item]);
         success = true;
       } catch {
-        // silent fail
+        // ClipboardItem-with-promise unsupported or rejected — fall through.
+      }
+    }
+
+    if (!success) {
+      // Legacy path: now that ClipboardItem failed, await the text and try
+      // the synchronous fallbacks. (May still need a second click on very old
+      // browsers, but those lack ClipboardItem entirely.)
+      const finalText = await shortenHighlightUrlsIn(text);
+      try {
+        await navigator.clipboard.writeText(finalText);
+        success = true;
+      } catch {
+        // Fallback for older browsers without the async clipboard API.
+        const ta = document.createElement("textarea");
+        ta.value = finalText;
+        ta.style.position = "fixed";
+        ta.style.top = "0";
+        ta.style.left = "0";
+        ta.style.opacity = "0";
+        document.body.appendChild(ta);
+        ta.focus();
+        ta.select();
+        try {
+          document.execCommand("copy");
+          success = true;
+        } catch {
+          // silent fail
+        }
+        document.body.removeChild(ta);
       }
-      document.body.removeChild(ta);
     }
 
     if (success) {