diff --git a/src/orb/webhook.ts b/src/orb/webhook.ts
index a1c2e23e05..2333ed9364 100644
--- a/src/orb/webhook.ts
+++ b/src/orb/webhook.ts
@@ -82,7 +82,16 @@ export async function handleOrbWebhook(c: Context<{ Bindings: Env }>): Promise<R
     return c.json({ error: "processing_failed", deliveryId }, 500);
   }
 
-  await recordOrbWebhookEvent(c.env, { ...eventMeta, status: "received" });
+  try {
+    await recordOrbWebhookEvent(c.env, { ...eventMeta, status: "received" });
+  } catch (error) {
+    // Distinct from orb_webhook_processing_failed above: the upsert/outcome writes DID succeed, only the
+    // webhook-event row failed to persist. Left unguarded this threw past the 202 below, leaving the delivery
+    // unrecorded (so a GitHub redelivery re-runs the already-successful processing) with no structured log for
+    // this specific mode. Return 500 so GitHub redelivers and the row is retried, with its own error event (#8883).
+    console.error(JSON.stringify({ level: "error", event: "orb_webhook_event_record_failed", ...eventMeta, message: String(error).slice(0, 200) }));
+    return c.json({ error: "event_record_failed", deliveryId }, 500);
+  }
   // Forward to a brokered self-host registered for this installation — but NEVER block the 202 we owe GitHub on it.
   // A push-mode forward POSTs to the container's relay URL with a 10s timeout; a slow (e.g. tailnet) container would
   // otherwise delay our response past GitHub's ~10s delivery deadline, so GitHub marks the delivery FAILED even
diff --git a/test/integration/orb-webhook.test.ts b/test/integration/orb-webhook.test.ts
index 4e9bd70401..b875b81346 100644
--- a/test/integration/orb-webhook.test.ts
+++ b/test/integration/orb-webhook.test.ts
@@ -63,6 +63,30 @@ describe("handleOrbWebhook (POST /v1/orb/webhook)", () => {
     errors.mockRestore();
   });
 
+  it("500 + distinct log when only the trailing webhook-event record write fails (#8883)", async () => {
+    const e = env();
+    const real = e.DB;
+    // The upsert/outcome writes succeed (so the earlier catch is NOT entered); throw only on the trailing
+    // orb_webhook_events INSERT (the status:"received" record), leaving the dedup SELECT read on the real DB.
+    (e as { DB: unknown }).DB = {
+      prepare: (sql: string) =>
+        sql.includes("orb_webhook_events") && sql.includes("INSERT")
+          ? { bind: () => ({ run: () => Promise.reject(new Error("boom")) }) }
+          : real.prepare(sql),
+    };
+    const errors = vi.spyOn(console, "error").mockImplementation(() => undefined);
+    const res = await post(e, INSTALL, { delivery: "rec-err" });
+    expect(res.status).toBe(500);
+    expect(await res.json()).toMatchObject({ error: "event_record_failed", deliveryId: "rec-err" });
+    // Distinct from orb_webhook_processing_failed: the processing succeeded, only the event-row write failed.
+    const processingLog = errors.mock.calls.map((c) => String(c[0])).find((line) => line.includes("orb_webhook_processing_failed"));
+    expect(processingLog).toBeUndefined();
+    const recordLog = errors.mock.calls.map((c) => String(c[0])).find((line) => line.includes("orb_webhook_event_record_failed"));
+    expect(recordLog).toBeDefined();
+    expect(JSON.parse(recordLog!)).toMatchObject({ level: "error", event: "orb_webhook_event_record_failed", deliveryId: "rec-err", eventName: "installation", installationId: 42, message: "Error: boom" });
+    errors.mockRestore();
+  });
+
   it("400 when the GitHub delivery or event header is missing", async () => {
     expect((await post(env(), INSTALL, { delivery: null as unknown as string })).status).toBe(400);
     expect((await post(env(), INSTALL, { event: null as unknown as string })).status).toBe(400);