diff --git a/server/index.ts b/server/index.ts
index bf96884..30407e2 100644
--- a/server/index.ts
+++ b/server/index.ts
@@ -997,6 +997,52 @@ async function runStartupDataPatches() {
     ON CONFLICT (file_key) DO NOTHING
   `).catch(() => {});
 
+  // Дозаполнение task_id/field_id у старых строк, вставленных без привязки
+  // (ранние версии трекинга). ON CONFLICT DO NOTHING их не обновляет.
+  await db.execute(sql`
+    UPDATE file_uploads fu
+    SET task_id = src.task_id, field_id = src.field_id
+    FROM (
+      SELECT DISTINCT
+        CASE
+          WHEN elem->>'url' LIKE '%/api/files/%' THEN regexp_replace(elem->>'url', '^.*/api/files/', '')
+          WHEN elem->>'url' LIKE '%/uploads/%' THEN regexp_replace(elem->>'url', '^.*/uploads/', '')
+        END AS fkey,
+        tfv.task_id,
+        tfv.field_id
+      FROM task_field_values tfv
+      JOIN form_fields ff ON tfv.field_id = ff.id
+      CROSS JOIN LATERAL jsonb_array_elements(
+        CASE WHEN jsonb_typeof(tfv.value) = 'array' THEN tfv.value ELSE jsonb_build_array(tfv.value) END
+      ) elem
+      WHERE ff.type = 'file'
+        AND (elem->>'url' LIKE '%/api/files/%' OR elem->>'url' LIKE '%/uploads/%')
+    ) src
+    WHERE fu.file_key = src.fkey
+      AND src.fkey IS NOT NULL
+      AND fu.task_id IS NULL
+  `).catch(() => {});
+  await db.execute(sql`
+    UPDATE file_uploads fu
+    SET task_id = src.task_id
+    FROM (
+      SELECT DISTINCT
+        CASE
+          WHEN att->>'url' LIKE '%/api/files/%' THEN regexp_replace(att->>'url', '^.*/api/files/', '')
+          WHEN att->>'url' LIKE '%/uploads/%' THEN regexp_replace(att->>'url', '^.*/uploads/', '')
+        END AS fkey,
+        tm.task_id
+      FROM task_messages tm
+      CROSS JOIN LATERAL jsonb_array_elements(tm.attachments) att
+      WHERE tm.attachments IS NOT NULL
+        AND jsonb_typeof(tm.attachments) = 'array'
+        AND (att->>'url' LIKE '%/api/files/%' OR att->>'url' LIKE '%/uploads/%')
+    ) src
+    WHERE fu.file_key = src.fkey
+      AND src.fkey IS NOT NULL
+      AND fu.task_id IS NULL
+  `).catch(() => {});
+
   // RLS policies are created by migration 0011_rls_tasks_notnull.sql.
   // Startup only activates ENABLE + FORCE ROW LEVEL SECURITY when ENABLE_RLS=true,
   // then verifies all tables are correctly protected before allowing traffic.
diff --git a/server/mcp.ts b/server/mcp.ts
index bb5d18c..8bad017 100644
--- a/server/mcp.ts
+++ b/server/mcp.ts
@@ -4288,7 +4288,12 @@ To block task creation from task.before_create, set: ctx.result = { allow: false
       }
       if (!belongsToTask) {
         const fieldValues = await storage.getTaskFieldValues(taskId, organizationId);
-        belongsToTask = fieldValues.some((fv) => typeof fv.value === 'string' && fv.value.includes(fileKey));
+        // value может быть объектом/массивом (file-поля), а не строкой —
+        // сериализуем перед поиском ключа
+        belongsToTask = fieldValues.some((fv) => {
+          const raw = typeof fv.value === 'string' ? fv.value : JSON.stringify(fv.value ?? '');
+          return raw.includes(fileKey);
+        });
       }
       if (!belongsToTask) {
         return mcpError(`Файл не относится к задаче ${taskId}`);
diff --git a/server/utils/file-tracking.ts b/server/utils/file-tracking.ts
index fb19d47..b129aec 100644
--- a/server/utils/file-tracking.ts
+++ b/server/utils/file-tracking.ts
@@ -78,13 +78,27 @@ interface FileReferenceRow {
  */
 export async function trackFileOnDemand(fileKey: string): Promise<boolean> {
   const existing = await db
-    .select({ id: fileUploads.id })
+    .select()
     .from(fileUploads)
     .where(eq(fileUploads.fileKey, fileKey))
     .limit(1);
-  if (existing.length > 0) return true;
 
   try {
+    // Уже отслеживается, но без привязки к задаче (старые backfill-строки) —
+    // пытаемся дозаполнить taskId/fieldId из ссылок
+    if (existing.length > 0) {
+      const row = existing[0];
+      if (row.taskId == null) {
+        const ref = await findFileReference(fileKey);
+        if (ref?.taskId != null) {
+          await db.update(fileUploads)
+            .set({ taskId: ref.taskId, fieldId: row.fieldId ?? ref.fieldId })
+            .where(eq(fileUploads.id, row.id));
+        }
+      }
+      return true;
+    }
+
     const ref = await findFileReference(fileKey);
     // uploadedBy NOT NULL в схеме — без владельца записать не сможем
     if (!ref || ref.uploadedBy == null) return false;