diff --git a/frontend/src/api/hooks.ts b/frontend/src/api/hooks.ts
index 27ba7c3..f44a707 100644
--- a/frontend/src/api/hooks.ts
+++ b/frontend/src/api/hooks.ts
@@ -525,6 +525,14 @@ export function usePipelineHealth(hours = 24) {
   return useGet<Record<string, unknown>>(['pipeline-health', hours], 'query', `/api/ops/pipeline/health?hours=${hours}`);
 }
 
+export function useRetryFailedExtractions() {
+  const qc = useQueryClient();
+  return useMutation({
+    mutationFn: () => apiPost<{ retried: number; message: string }>('query', '/api/ops/pipeline/retry-failed', {}),
+    onSuccess: () => qc.invalidateQueries({ queryKey: ['pipeline-health'] }),
+  });
+}
+
 export function useIngestionSummary(hours = 24) {
   return useGet<Record<string, unknown>>(['ingestion-summary', hours], 'query', `/api/ops/ingestion/summary?hours=${hours}`);
 }
diff --git a/frontend/src/pages/OpsPipeline.tsx b/frontend/src/pages/OpsPipeline.tsx
index 724898b..10f673b 100644
--- a/frontend/src/pages/OpsPipeline.tsx
+++ b/frontend/src/pages/OpsPipeline.tsx
@@ -1,5 +1,5 @@
 import { useState, useEffect } from 'react';
-import { usePipelineHealth } from '../api/hooks';
+import { usePipelineHealth, useRetryFailedExtractions } from '../api/hooks';
 import { LoadingSpinner, DateRangeSelector, Card } from '../components/ui';
 
 const QUEUE_LABELS: Record<string, string> = {
@@ -53,6 +53,7 @@ export function OpsPipelinePage() {
   const [hours, setHours] = useState(24);
   const { data, isLoading } = usePipelineHealth(hours);
   const stream = usePipelineStream();
+  const retryMutation = useRetryFailedExtractions();
 
   if (isLoading) return <LoadingSpinner />;
 
@@ -70,6 +71,8 @@ export function OpsPipelinePage() {
         .map((s) => [s.status, s.doc_count]),
     );
 
+  const failedCount = docStages['extraction_failed'] ?? 0;
+
   // Separate DLQ entries from regular queues
   const dlqEntries = Object.entries(queueDepths).filter(([k]) => k.startsWith('dlq:'));
   const regularQueues = Object.entries(QUEUE_LABELS);
@@ -79,6 +82,22 @@ export function OpsPipelinePage() {
       <div className="flex items-center justify-between">
         <h1 className="text-xl font-semibold text-gray-100">Pipeline Health</h1>
         <div className="flex items-center gap-3">
+          {failedCount > 0 && (
+            <button
+              type="button"
+              onClick={() => retryMutation.mutate()}
+              disabled={retryMutation.isPending}
+              className="rounded-md bg-amber-600 px-3 py-1.5 text-xs font-medium text-white hover:bg-amber-500 disabled:opacity-50"
+            >
+              {retryMutation.isPending ? 'Retrying…' : `Retry Failed (${failedCount})`}
+            </button>
+          )}
+          {retryMutation.isSuccess && (
+            <span className="text-xs text-green-400">{retryMutation.data.message}</span>
+          )}
+          {retryMutation.isError && (
+            <span className="text-xs text-red-400">Retry failed</span>
+          )}
           {stream && (
             <span className="flex items-center gap-1.5 text-xs text-green-400">
               <span className="inline-block h-2 w-2 rounded-full bg-green-400 animate-pulse" aria-hidden="true" />
diff --git a/frontend/src/test/mocks/handlers.ts b/frontend/src/test/mocks/handlers.ts
index 61f5d5a..11be829 100644
--- a/frontend/src/test/mocks/handlers.ts
+++ b/frontend/src/test/mocks/handlers.ts
@@ -104,7 +104,8 @@ export const handlers = [
     return HttpResponse.json({ id: 'lockout-new', ticker: body.ticker, reason: body.reason, lockout_type: body.lockout_type ?? 'manual', expires_at: new Date(Date.now() + ((body.duration_minutes as number) ?? 60) * 60000).toISOString(), created_at: new Date().toISOString() }, { status: 201 });
   }),
   http.delete('/api/admin/trading/lockouts/:id', () => HttpResponse.json({ status: 'deleted' })),
-  http.get('/api/ops/pipeline/health', () => HttpResponse.json({ hours: 24, document_stages: [{ status: 'extracted', doc_count: 5 }], parsing: {}, extraction: {}, aggregation: {} })),
+  http.get('/api/ops/pipeline/health', () => HttpResponse.json({ hours: 24, document_stages: [{ status: 'extracted', doc_count: 5 }], parsing: {}, extraction: {}, aggregation: {}, queue_depths: {} })),
+  http.post('/api/ops/pipeline/retry-failed', () => HttpResponse.json({ retried: 10, message: 'Re-enqueued 10 documents for extraction' })),
   http.get('/api/ops/ingestion/summary', () => HttpResponse.json({ total_runs: 10, completed: 8, failed: 2, total_items_fetched: 50, total_items_new: 12, by_source_type: [] })),
   http.get('/api/ops/ingestion/throughput', () => HttpResponse.json([])),
   http.get('/api/ops/model/performance', () => HttpResponse.json({ total_extractions: 20, success_rate: 0.9, avg_duration_ms: 1500, retry_rate: 0.05, avg_confidence: 0.8 })),
diff --git a/services/api/app.py b/services/api/app.py
index d19fbc5..fac2dde 100644
--- a/services/api/app.py
+++ b/services/api/app.py
@@ -1869,6 +1869,58 @@ async def pipeline_stream(request: Request):
     )
 
 
+@app.post("/api/ops/pipeline/retry-failed")
+async def retry_failed_extractions_endpoint():
+    """Re-enqueue documents stuck in extraction_failed for another attempt.
+
+    Resets up to 200 extraction_failed documents back to 'parsed',
+    deletes their failed intelligence rows, and pushes them onto the
+    extraction queue.  Returns the count of documents re-enqueued.
+    """
+    rows = await pool.fetch(
+        """SELECT d.id, d.document_type, dcm.ticker
+           FROM documents d
+           LEFT JOIN document_company_mentions dcm ON d.id = dcm.document_id
+           WHERE d.status = 'extraction_failed'
+           ORDER BY d.updated_at ASC
+           LIMIT 200""",
+    )
+
+    if not rows:
+        return {"retried": 0, "message": "No extraction-failed documents to retry"}
+
+    doc_ids = []
+    for row in rows:
+        doc_type = row["document_type"]
+        if doc_type == "macro_event":
+            target = "stonks:queue:macro_classification"
+        else:
+            target = "stonks:queue:extraction"
+
+        await rds.rpush(target, json.dumps({
+            "document_id": str(row["id"]),
+            "ticker": row["ticker"] or "",
+        }))
+        doc_ids.append(row["id"])
+
+    # Delete failed intelligence rows so extractor starts fresh
+    await pool.execute(
+        """DELETE FROM document_intelligence
+           WHERE document_id = ANY($1::uuid[])
+             AND validation_status = 'failed'""",
+        doc_ids,
+    )
+    # Reset status to 'parsed' and touch updated_at
+    await pool.execute(
+        """UPDATE documents
+           SET status = 'parsed', updated_at = NOW()
+           WHERE id = ANY($1::uuid[])""",
+        doc_ids,
+    )
+
+    return {"retried": len(doc_ids), "message": f"Re-enqueued {len(doc_ids)} documents for extraction"}
+
+
 @app.get("/api/ops/sources/coverage-gaps")
 async def get_source_coverage_gaps():
     """Identify symbols with missing or insufficient source coverage.
diff --git a/services/scheduler/app.py b/services/scheduler/app.py
index 5eb774f..29a80a6 100644
--- a/services/scheduler/app.py
+++ b/services/scheduler/app.py
@@ -499,6 +499,7 @@ async def main() -> None:
 
     logger.info("Scheduler started (tick=%ds)", SCHEDULER_TICK)
     recovery_counter = 0
+    retry_counter = 0
     cleanup_counter = 0
     try:
         while True:
@@ -511,6 +512,11 @@ async def main() -> None:
                         if recovery_counter >= 20:
                             recovery_counter = 0
                             await recover_stale_documents(pool, rds)
+                        # Retry extraction failures every ~40 cycles (~10 minutes)
+                        retry_counter += 1
+                        if retry_counter >= 40:
+                            retry_counter = 0
+                            await retry_failed_extractions(pool, rds)
                         # Run signal cleanup periodically (~25 minutes)
                         cleanup_counter += 1
                         if cleanup_counter >= CLEANUP_CYCLE_INTERVAL:
@@ -529,6 +535,9 @@ async def main() -> None:
 # How long a document can sit in "parsed" before we consider it orphaned
 STALE_PARSED_THRESHOLD_MINUTES: int = 30
 
+# How long after an extraction failure before we retry
+EXTRACTION_FAILED_RETRY_MINUTES: int = 60
+
 
 async def recover_stale_documents(pool: asyncpg.Pool, rds: aioredis.Redis) -> int:
     """Re-enqueue documents stuck in 'parsed' status for extraction.
@@ -584,6 +593,67 @@ async def recover_stale_documents(pool: asyncpg.Pool, rds: aioredis.Redis) -> in
     return enqueued
 
 
+async def retry_failed_extractions(pool: asyncpg.Pool, rds: aioredis.Redis) -> int:
+    """Re-enqueue documents stuck in 'extraction_failed' for another attempt.
+
+    Resets status to 'parsed', deletes the failed intelligence row so the
+    extractor treats them as fresh, and pushes them onto the extraction queue.
+
+    Only retries documents whose last attempt was at least
+    EXTRACTION_FAILED_RETRY_MINUTES ago to avoid tight retry loops.
+
+    Returns the number of documents re-enqueued.
+    """
+    rows = await pool.fetch(
+        """SELECT d.id, d.document_type, dcm.ticker
+           FROM documents d
+           LEFT JOIN document_company_mentions dcm ON d.id = dcm.document_id
+           WHERE d.status = 'extraction_failed'
+             AND d.updated_at < NOW() - INTERVAL '1 minute' * $1
+           ORDER BY d.updated_at ASC
+           LIMIT 100""",
+        EXTRACTION_FAILED_RETRY_MINUTES,
+    )
+
+    if not rows:
+        return 0
+
+    enqueued = 0
+    doc_ids = []
+    for row in rows:
+        doc_type = row["document_type"]
+        if doc_type == "macro_event":
+            target = queue_key(QUEUE_MACRO_CLASSIFICATION)
+        else:
+            target = queue_key(QUEUE_EXTRACTION)
+
+        await rds.rpush(target, json.dumps({
+            "document_id": str(row["id"]),
+            "ticker": row["ticker"] or "",
+        }))
+        doc_ids.append(row["id"])
+        enqueued += 1
+
+    if doc_ids:
+        # Delete failed intelligence rows so extractor starts fresh
+        await pool.execute(
+            """DELETE FROM document_intelligence
+               WHERE document_id = ANY($1::uuid[])
+                 AND validation_status = 'failed'""",
+            doc_ids,
+        )
+        # Reset status to 'parsed' and touch updated_at
+        await pool.execute(
+            """UPDATE documents
+               SET status = 'parsed', updated_at = NOW()
+               WHERE id = ANY($1::uuid[])""",
+            doc_ids,
+        )
+
+    logger.info("Retried %d extraction-failed documents", enqueued)
+    return enqueued
+
+
 # How often to run competitive signal cleanup (every ~100 cycles = ~25 minutes)
 CLEANUP_CYCLE_INTERVAL: int = 100
 # Keep competitive signals for this many days