diff --git a/components/social/share-post-sheet.tsx b/components/social/share-post-sheet.tsx
index 6b390aec..ececacb9 100644
--- a/components/social/share-post-sheet.tsx
+++ b/components/social/share-post-sheet.tsx
@@ -94,6 +94,15 @@ export function SharePostSheet({
   // on mount; combined with `isMobile` to gate the "More" tile so the
   // affordance only appears where it can do something useful.
   const [nativeShareSupported, setNativeShareSupported] = useState(false);
+  // Pre-fetched File ready to attach to navigator.share. We build this
+  // when the sheet opens — NOT lazily inside the "More" click handler —
+  // because iOS Safari requires navigator.share() to fire within the
+  // transient user activation window (~5 s after the tap). Awaiting a
+  // network fetch in between burns that window and iOS rejects the
+  // share. With the file pre-fetched, the tap → share() call is
+  // synchronous in the same task.
+  const [shareableFile, setShareableFile] = useState<File | null>(null);
+  const [imageFetchError, setImageFetchError] = useState<string | null>(null);
 
   useEffect(() => {
     setNativeShareSupported(
@@ -145,6 +154,63 @@ export function SharePostSheet({
     };
   }, [open, authorHandle, post.id]);
 
+  // Pre-fetch the first image as a File while the sheet is open. By
+  // the time the user taps "More" the File is already in memory, so
+  // navigator.share fires synchronously in the same tap — preserving
+  // iOS Safari's user-activation token. Without this, awaiting the
+  // fetch INSIDE the click handler burns the activation window and
+  // iOS rejects the share with NotAllowedError.
+  //
+  // Failures (CORS-blocked fetch, 4xx, network error) are remembered
+  // in imageFetchError so the click handler can toast a useful
+  // explanation. We don't toast at fetch time because the user hasn't
+  // committed to sharing yet — that would feel like noise.
+  useEffect(() => {
+    if (!open || !firstImage) {
+      setShareableFile(null);
+      setImageFetchError(null);
+      return;
+    }
+    let cancelled = false;
+    setShareableFile(null);
+    setImageFetchError(null);
+    (async () => {
+      try {
+        const res = await fetch(firstImage, { mode: "cors" });
+        if (cancelled) return;
+        if (!res.ok) {
+          setImageFetchError(`HTTP ${res.status}`);
+          console.warn(
+            `[share] image pre-fetch returned ${res.status} for`,
+            firstImage,
+          );
+          return;
+        }
+        const blob = await res.blob();
+        if (cancelled) return;
+        const ext = (blob.type.split("/")[1] || "jpg").toLowerCase();
+        const file = new File([blob], `share.${ext}`, {
+          type: blob.type || "image/jpeg",
+        });
+        setShareableFile(file);
+      } catch (err) {
+        if (cancelled) return;
+        setImageFetchError("cors");
+        // Almost always a CORS preflight failure when the public R2
+        // domain is a separate hostname. Log so it's visible in
+        // DevTools when the user reports "image didn't attach".
+        console.warn(
+          "[share] image pre-fetch failed (likely CORS) for",
+          firstImage,
+          err,
+        );
+      }
+    })();
+    return () => {
+      cancelled = true;
+    };
+  }, [open, firstImage]);
+
   // Canonical share payload — quote, reference, link. Built lazily because
   // shortUrl arrives async; while loading we render a spinner instead.
   const shareText = useMemo(() => {
@@ -167,44 +233,81 @@ export function SharePostSheet({
     onClose();
   }
 
-  async function shareNative() {
+  function shareNative() {
+    // Crucially: this function must NOT await anything before calling
+    // navigator.share. iOS Safari only honours the call inside the
+    // tap's transient user-activation window; any awaited fetch /
+    // microtask here would burn it and the share would be rejected as
+    // NotAllowedError. The image is pre-fetched in the useEffect
+    // above; here we just pick it up and fire.
     if (!nativeShareSupported) return;
     const payload: ShareData = {
       title: reference,
       text: shareText,
     };
-    // Bonus: attach the first image as a File so the recipient gets
-    // the visual. Requires (a) R2 to allow CORS GET on the public URL
-    // and (b) navigator.canShare to accept the File. If either fails
-    // we silently degrade to text-only — the quote + URL still go
-    // through, which is the contract.
-    if (firstImage) {
-      try {
-        const res = await fetch(firstImage, { mode: "cors" });
-        if (res.ok) {
-          const blob = await res.blob();
-          const ext = (blob.type.split("/")[1] || "jpg").toLowerCase();
-          const file = new File([blob], `share.${ext}`, {
-            type: blob.type || "image/jpeg",
-          });
-          if (
-            typeof navigator.canShare === "function" &&
-            navigator.canShare({ files: [file] })
-          ) {
-            payload.files = [file];
-          }
-        }
-      } catch {
-        // CORS-blocked or network error — proceed without files.
+    let attachedImage = false;
+    if (
+      shareableFile &&
+      typeof navigator.canShare === "function" &&
+      navigator.canShare({ files: [shareableFile] })
+    ) {
+      payload.files = [shareableFile];
+      attachedImage = true;
+    } else if (firstImage && !shareableFile) {
+      // Image existed on the post but pre-fetch didn't complete
+      // (or failed). Surface the reason so the user knows why the
+      // share is text-only — at the moment they actually share, not
+      // earlier when the sheet first opened.
+      if (imageFetchError === "cors") {
+        toast(
+          "Couldn't load image (CORS) — sharing text only. Check R2 CORS policy.",
+          { duration: 4000 },
+        );
+      } else if (imageFetchError) {
+        toast(`Image not available (${imageFetchError}) — sharing text only`, {
+          duration: 3000,
+        });
+      } else {
+        toast("Still loading image — sharing text only", { duration: 2500 });
       }
+    } else if (
+      firstImage &&
+      shareableFile &&
+      typeof navigator.canShare === "function" &&
+      !navigator.canShare({ files: [shareableFile] })
+    ) {
+      // File is ready but the platform refuses it (rare on iOS — more
+      // often desktop Chrome / Firefox). The "More" tile is already
+      // gated on isMobile so this branch mainly catches edge cases.
+      console.warn(
+        "[share] navigator.canShare rejected files on this platform",
+      );
+      toast(
+        "Your browser can't share images here — sharing text only",
+        { duration: 3000 },
+      );
     }
-    try {
-      await navigator.share(payload);
-      onClose();
-    } catch {
-      // User cancelled the share sheet; leave the drawer open so they
-      // can pick another target.
-    }
+
+    // Fire-and-forget — we don't await so React doesn't get a chance
+    // to render in between the tap and the share call. The .catch
+    // tail handles AbortError (user cancel) vs real failure for
+    // diagnostics.
+    navigator
+      .share(payload)
+      .then(() => onClose())
+      .catch((err) => {
+        const aborted =
+          err instanceof DOMException && err.name === "AbortError";
+        if (!aborted) {
+          console.warn("[share] navigator.share threw", err);
+          toast.error(
+            `Share failed${
+              attachedImage ? " (image may be too large for this app)" : ""
+            }`,
+            { duration: 3000 },
+          );
+        }
+      });
   }
 
   // Channel tiles — kept in a single declarative list so the JSX is just