diff --git a/frontend/src/routes/+page.svelte b/frontend/src/routes/+page.svelte
index 055acfb..b714dd2 100644
--- a/frontend/src/routes/+page.svelte
+++ b/frontend/src/routes/+page.svelte
@@ -119,7 +119,15 @@
     const sameServerBrief =
       view && view.generated_at && fetched.generated_at && view.generated_at === fetched.generated_at;
     if (!fresh && sameServerBrief && Array.isArray(view.items) && view.items.length) {
-      brief = { ...fetched, items: view.items };
+      // Same server brief: keep the user's pinned order + replacements, but
+      // refresh server-owned metadata by id. image_url especially is enriched
+      // AFTER the brief is built (without bumping generated_at), so a verbatim
+      // pinned copy can stay imageless forever. Items the user swapped in
+      // (absent from the fresh brief) keep their own data.
+      const freshById = new Map(fetched.items.map((a) => [a.id, a]));
+      const items = view.items.map((it) => freshById.get(it.id) ?? it);
+      brief = { ...fetched, items };
+      P.saveJSON(BRIEF_VIEW_KEY, { generated_at: fetched.generated_at, items });
     } else {
       brief = fetched;
       P.saveJSON(BRIEF_VIEW_KEY, { generated_at: fetched.generated_at, items: fetched.items });
diff --git a/goodnews/enrich.py b/goodnews/enrich.py
index f36a707..966e7ac 100644
--- a/goodnews/enrich.py
+++ b/goodnews/enrich.py
@@ -146,27 +146,36 @@ def fetch_og_image(url: str | None) -> str | None:
     return None  # too many redirects
 
 
-def enrich_brief_images(conn: sqlite3.Connection, brief_date: str, fetch=fetch_og_image, limit: int = 5) -> int:
-    """Fetch a hero-quality image for brief items that lack one (once each).
+def enrich_brief_images(
+    conn: sqlite3.Connection, brief_date: str, fetch=fetch_og_image, limit: int = 7, retry_days: int = 2
+) -> int:
+    """Fetch a hero-quality image for brief items that lack one.
 
-    Only touches the given date's brief items with no image and not yet checked;
-    stamps image_checked_at either way so failures are not retried forever.
+    Any of the brief's items can become the hero (via the client's fallback or a
+    replace), so this covers the whole brief (limit defaults to the brief size, 7),
+    not just the top few. Items already carrying an image are left alone; items
+    still without one are retried after `retry_days` so a transient fetch failure
+    or a weaker earlier extractor doesn't mark an article imageless forever.
     Returns how many images were newly found.
     """
-    # Brief items not yet checked. We fetch even when a feed image exists,
-    # because feed thumbnails are often tiny and the hero is shown large — a
-    # page's og:image (the social-share image) is the better hero visual.
+    # Fetch even when a feed image exists, because feed thumbnails are often tiny
+    # and the hero is shown large — a page's og:image is the better hero visual.
     rows = conn.execute(
         """
         SELECT a.id, a.canonical_url
         FROM daily_briefs b
         JOIN daily_brief_items bi ON bi.brief_id = b.id
         JOIN articles a ON a.id = bi.article_id
-        WHERE b.brief_date = ? AND a.image_checked_at IS NULL
+        WHERE b.brief_date = ?
+          AND (
+            a.image_checked_at IS NULL
+            OR ((a.image_url IS NULL OR a.image_url = '')
+                AND a.image_checked_at < datetime('now', ?))
+          )
         ORDER BY bi.rank
         LIMIT ?
         """,
-        (brief_date, limit),
+        (brief_date, f"-{retry_days} days", limit),
     ).fetchall()
 
     found = 0