diff --git a/cmd/server/main.go b/cmd/server/main.go
index b6a69bb..cd44c82 100644
--- a/cmd/server/main.go
+++ b/cmd/server/main.go
@@ -558,17 +558,81 @@ func (a *app) probeMediaMetadata(ctx context.Context) componentProbe {
 		return componentProbe{Name: "media_metadata", Status: "down", LatencyMs: time.Since(start).Milliseconds(), Error: err.Error()}
 	}
 	if missingFiles > 0 {
+		recent, recentErr := a.recentMissingMedia(ctx)
+		details := map[string]any{
+			"messages_with_media": withMedia,
+			"missing_media_files": missingFiles,
+		}
+		if recentErr != nil {
+			details["recent_error"] = recentErr.Error()
+		} else {
+			details["recent_missing_media"] = recent
+		}
 		return componentProbe{
 			Name:      "media_metadata",
 			Status:    "down",
 			LatencyMs: time.Since(start).Milliseconds(),
 			Error: "messages_with_media=" + strconv.FormatInt(withMedia, 10) +
 				" missing_media_files=" + strconv.FormatInt(missingFiles, 10),
+			Details: details,
 		}
 	}
 	return componentProbe{Name: "media_metadata", Status: "ok", LatencyMs: time.Since(start).Milliseconds()}
 }
 
+func (a *app) recentMissingMedia(ctx context.Context) ([]map[string]any, error) {
+	rows, err := a.db.Query(ctx, `
+		SELECT
+			m.id,
+			m.tg_message_id,
+			m.date,
+			c.id AS channel_id,
+			c.identifier,
+			COALESCE(c.title, '') AS channel_title,
+			s.slug,
+			s.title AS section_title
+		FROM messages m
+		JOIN channels c ON c.id = m.channel_id
+		LEFT JOIN sections s ON s.id = c.section_id
+		WHERE m.has_media = true
+		  AND jsonb_array_length(COALESCE(m.media_files, '[]'::jsonb)) = 0
+		ORDER BY m.date DESC, m.id DESC
+		LIMIT 5`)
+	if err != nil {
+		return nil, err
+	}
+	defer rows.Close()
+
+	out := make([]map[string]any, 0, 5)
+	for rows.Next() {
+		var (
+			id           int64
+			tgMessageID  int64
+			date         time.Time
+			channelID    int64
+			identifier   string
+			channelTitle string
+			sectionSlug  sql.NullString
+			sectionTitle sql.NullString
+		)
+		if err := rows.Scan(&id, &tgMessageID, &date, &channelID, &identifier, &channelTitle, &sectionSlug, &sectionTitle); err != nil {
+			return nil, err
+		}
+		out = append(out, map[string]any{
+			"message_id":    id,
+			"tg_message_id": tgMessageID,
+			"message_date":  date,
+			"channel_id":    channelID,
+			"identifier":    identifier,
+			"channel_title": nullableString(channelTitle),
+			"section_slug":  nullString(sectionSlug),
+			"section_title": nullString(sectionTitle),
+			"repair_action": "/api/v1/channels/" + strconv.FormatInt(channelID, 10) + "/backfill-media",
+		})
+	}
+	return out, rows.Err()
+}
+
 func (a *app) handleAccessMe(w http.ResponseWriter, r *http.Request) {
 	scope := readAccess(r)
 	writeJSON(w, http.StatusOK, map[string]any{
diff --git a/src/parser_bot/scheduler/poller.py b/src/parser_bot/scheduler/poller.py
index 428bf0a..a3609a8 100644
--- a/src/parser_bot/scheduler/poller.py
+++ b/src/parser_bot/scheduler/poller.py
@@ -2,7 +2,7 @@ from datetime import datetime, timezone
 
 import structlog
 from apscheduler.schedulers.asyncio import AsyncIOScheduler
-from sqlalchemy import func, select
+from sqlalchemy import func, or_, select
 from sqlalchemy.dialects.postgresql import insert as pg_insert
 from sqlalchemy.exc import IntegrityError
 
@@ -262,10 +262,15 @@ async def backfill_media(channel_id: int, batch_size: int = 50) -> dict[str, int
         if channel is None:
             raise RuntimeError("channel not found")
 
+        missing_media_condition = or_(
+            Message.media_files.is_(None),
+            func.jsonb_array_length(Message.media_files) == 0,
+        )
+
         pending_q = select(func.count(Message.id)).where(
             Message.channel_id == channel_id,
             Message.has_media.is_(True),
-            Message.media_files.is_(None),
+            missing_media_condition,
         )
         pending_total = (await session.execute(pending_q)).scalar_one()
 
@@ -275,7 +280,7 @@ async def backfill_media(channel_id: int, batch_size: int = 50) -> dict[str, int
                 .where(
                     Message.channel_id == channel_id,
                     Message.has_media.is_(True),
-                    Message.media_files.is_(None),
+                    missing_media_condition,
                 )
                 .order_by(Message.tg_message_id.asc())
                 .limit(batch_size)