diff --git a/src/app/api/v1/admin/webhooks/[webhookId]/deliveries/[deliveryId]/redeliver/route.ts b/src/app/api/v1/admin/webhooks/[webhookId]/deliveries/[deliveryId]/redeliver/route.ts
new file mode 100644
index 0000000..2d0c989
--- /dev/null
+++ b/src/app/api/v1/admin/webhooks/[webhookId]/deliveries/[deliveryId]/redeliver/route.ts
@@ -0,0 +1,30 @@
+import { NextResponse } from 'next/server';
+
+import { withAuth, withPermission } from '@/lib/api/helpers';
+import { redeliverWebhookDelivery } from '@/lib/services/webhooks.service';
+import { errorResponse, NotFoundError } from '@/lib/errors';
+
+/**
+ * Admin replay for a previously failed/dead-letter webhook delivery.
+ * Spawns a fresh `pending` row + enqueues a new BullMQ job so the
+ * original delivery's failure response is preserved for audit while
+ * the replay flows through the standard worker (HMAC-signed, SSRF
+ * gated, dead-lettered after max retries).
+ */
+export const POST = withAuth(
+  withPermission('admin', 'manage_webhooks', async (_req, ctx, params) => {
+    try {
+      const { webhookId, deliveryId } = params;
+      if (!webhookId || !deliveryId) throw new NotFoundError('Delivery');
+      const result = await redeliverWebhookDelivery(ctx.portId, webhookId, deliveryId, {
+        userId: ctx.userId,
+        portId: ctx.portId,
+        ipAddress: ctx.ipAddress,
+        userAgent: ctx.userAgent,
+      });
+      return NextResponse.json({ data: result });
+    } catch (error) {
+      return errorResponse(error);
+    }
+  }),
+);
diff --git a/src/components/admin/webhooks/webhook-delivery-log.tsx b/src/components/admin/webhooks/webhook-delivery-log.tsx
index 3eef9df..2266ad7 100644
--- a/src/components/admin/webhooks/webhook-delivery-log.tsx
+++ b/src/components/admin/webhooks/webhook-delivery-log.tsx
@@ -1,6 +1,8 @@
 'use client';
 
 import { useEffect, useState } from 'react';
+import { RotateCcw } from 'lucide-react';
+import { toast } from 'sonner';
 import { Badge } from '@/components/ui/badge';
 import { Button } from '@/components/ui/button';
 import {
@@ -39,6 +41,22 @@ export function WebhookDeliveryLog({ webhookId }: Props) {
   const [total, setTotal] = useState(0);
   const [page, setPage] = useState(1);
   const [loading, setLoading] = useState(true);
+  const [retrying, setRetrying] = useState<string | null>(null);
+
+  async function retry(deliveryId: string) {
+    setRetrying(deliveryId);
+    try {
+      await apiFetch(`/api/v1/admin/webhooks/${webhookId}/deliveries/${deliveryId}/redeliver`, {
+        method: 'POST',
+      });
+      toast.success('Replay queued');
+      await load(page);
+    } catch (err) {
+      toast.error(err instanceof Error ? err.message : 'Replay failed');
+    } finally {
+      setRetrying(null);
+    }
+  }
 
   async function load(p: number) {
     setLoading(true);
@@ -80,6 +98,7 @@ export function WebhookDeliveryLog({ webhookId }: Props) {
             <TableHead>HTTP</TableHead>
             <TableHead>Attempt</TableHead>
             <TableHead>Time</TableHead>
+            <TableHead className="w-16 text-right">Replay</TableHead>
           </TableRow>
         </TableHeader>
         <TableBody>
@@ -96,6 +115,22 @@ export function WebhookDeliveryLog({ webhookId }: Props) {
                   ? new Date(d.deliveredAt).toLocaleString()
                   : new Date(d.createdAt).toLocaleString()}
               </TableCell>
+              <TableCell className="text-right">
+                {(d.status === 'failed' || d.status === 'dead_letter') && (
+                  <Button
+                    variant="ghost"
+                    size="sm"
+                    disabled={retrying === d.id}
+                    onClick={() => retry(d.id)}
+                    title="Replay this delivery"
+                    aria-label="Replay this delivery"
+                  >
+                    <RotateCcw
+                      className={`h-3.5 w-3.5 ${retrying === d.id ? 'animate-spin' : ''}`}
+                    />
+                  </Button>
+                )}
+              </TableCell>
             </TableRow>
           ))}
         </TableBody>
diff --git a/src/lib/services/webhooks.service.ts b/src/lib/services/webhooks.service.ts
index 0d122e1..d2cb07a 100644
--- a/src/lib/services/webhooks.service.ts
+++ b/src/lib/services/webhooks.service.ts
@@ -269,6 +269,78 @@ export async function listDeliveries(
   return { data, total };
 }
 
+// ─── Redeliver a previously failed / dead-letter delivery ───────────────────
+
+/**
+ * Clones a failed or dead-letter delivery into a fresh `pending` row and
+ * re-enqueues it. Multi-tenant safe: looks up the source delivery via
+ * its webhook → port. Idempotency: each redeliver creates a new row so
+ * the original record (and its failure response body) is preserved for
+ * audit. The new delivery's payload includes a `retried_from` marker
+ * that downstream receivers can use to recognise replays.
+ */
+export async function redeliverWebhookDelivery(
+  portId: string,
+  webhookId: string,
+  deliveryId: string,
+  meta: AuditMeta,
+) {
+  const webhook = await db.query.webhooks.findFirst({
+    where: eq(webhooks.id, webhookId),
+  });
+  if (!webhook || webhook.portId !== portId) {
+    throw new NotFoundError('Webhook');
+  }
+  if (!webhook.isActive) {
+    throw new NotFoundError('Webhook is inactive');
+  }
+
+  const [source] = await db
+    .select()
+    .from(webhookDeliveries)
+    .where(and(eq(webhookDeliveries.id, deliveryId), eq(webhookDeliveries.webhookId, webhookId)))
+    .limit(1);
+  if (!source) throw new NotFoundError('Delivery');
+
+  const replayPayload = {
+    ...(source.payload as Record<string, unknown>),
+    retried_from: deliveryId,
+    retried_at: new Date().toISOString(),
+  };
+
+  const [next] = await db
+    .insert(webhookDeliveries)
+    .values({
+      webhookId,
+      eventType: source.eventType,
+      payload: replayPayload,
+      status: 'pending',
+    })
+    .returning();
+
+  const queue = getQueue('webhooks');
+  await queue.add('deliver', {
+    webhookId,
+    portId,
+    event: source.eventType,
+    deliveryId: next!.id,
+    payload: replayPayload,
+  });
+
+  void createAuditLog({
+    userId: meta.userId,
+    portId,
+    action: 'send',
+    entityType: 'webhook_delivery',
+    entityId: next!.id,
+    metadata: { redeliveredFrom: deliveryId, originalStatus: source.status },
+    ipAddress: meta.ipAddress,
+    userAgent: meta.userAgent,
+  });
+
+  return { deliveryId: next!.id, status: 'queued' };
+}
+
 // ─── Send Test Webhook ────────────────────────────────────────────────────────
 
 export async function sendTestWebhook(portId: string, webhookId: string, eventType: WebhookEvent) {