diff --git a/apps/api/src/services/platform_operator_service.py b/apps/api/src/services/platform_operator_service.py
index 6654f2e5..60062df4 100644
--- a/apps/api/src/services/platform_operator_service.py
+++ b/apps/api/src/services/platform_operator_service.py
@@ -271,10 +271,26 @@ def _outbound_timeline_title(
     channel_type: str,
     message_type: str,
     content_preview: str | None,
+    callback_reply: dict[str, Any] | None = None,
 ) -> str:
     """將 legacy Telegram outbound 分類成 Operator 看得懂的語義標題。"""
     channel = channel_type.upper()
     preview = content_preview or ""
+    if callback_reply:
+        action = str(callback_reply.get("action") or "").strip()
+        status = str(callback_reply.get("status") or "").strip()
+        action_label = {
+            "detail": "詳情",
+            "history": "歷史",
+        }.get(action, action or "Callback")
+        status_label = {
+            "callback_reply_sent": "已送出",
+            "callback_reply_fallback_sent": " fallback 已送出",
+            "callback_reply_rescue_sent": "救援已送出",
+            "callback_reply_failed": "送出失敗",
+        }.get(status, status or "已記錄")
+        return f"{channel}：{action_label}回覆{status_label}"
+
     if "RUNBOOK REVIEW" in preview:
         return f"{channel}：Runbook 待人工審核"
     if "[AWOOOI CI/CD]" in preview or "AWOOOI CI/CD" in preview:
@@ -299,6 +315,73 @@ def _outbound_timeline_title(
     return f"{channel}：{fallback}"
 
 
+def _outbound_callback_reply(source_envelope: Any) -> dict[str, Any] | None:
+    """Extract Telegram callback reply evidence from outbound source envelope."""
+    if not isinstance(source_envelope, dict):
+        return None
+    callback_reply = source_envelope.get("callback_reply")
+    return callback_reply if isinstance(callback_reply, dict) else None
+
+
+def _outbound_timeline_status(
+    send_status: str,
+    callback_reply: dict[str, Any] | None,
+) -> str:
+    """Prefer callback delivery status when the outbound row records one."""
+    if callback_reply:
+        status = callback_reply.get("status")
+        if isinstance(status, str) and status:
+            return status
+    return send_status
+
+
+def _outbound_timeline_summary(
+    *,
+    content_preview: str | None,
+    send_error: str | None,
+    callback_reply: dict[str, Any] | None,
+) -> str | None:
+    """Summarize callback reply state without forcing operators to inspect raw JSON."""
+    if not callback_reply:
+        return content_preview or send_error
+
+    parts = [
+        f"callback={callback_reply.get('action') or '--'}",
+        f"incident={callback_reply.get('incident_id') or '--'}",
+        f"status={callback_reply.get('status') or '--'}",
+    ]
+    parse_mode = callback_reply.get("parse_mode")
+    if parse_mode:
+        parts.append(f"parse_mode={parse_mode}")
+    error = callback_reply.get("error")
+    if error:
+        parts.append(f"error={error}")
+    if content_preview:
+        parts.append(str(content_preview))
+    return " · ".join(parts)
+
+
+def _outbound_timeline_metadata(
+    row: AwoooPOutboundMessage,
+    callback_reply: dict[str, Any] | None,
+) -> dict[str, Any]:
+    """Build compact outbound metadata with callback fields first when present."""
+    metadata: dict[str, Any] = {}
+    if callback_reply:
+        metadata.update({
+            "callback_status": callback_reply.get("status"),
+            "callback_action": callback_reply.get("action"),
+            "callback_incident_id": callback_reply.get("incident_id"),
+            "callback_parse_mode": callback_reply.get("parse_mode"),
+        })
+    metadata.update({
+        "message_type": row.message_type,
+        "provider_message_id": row.provider_message_id,
+        "triggered_by_state": row.triggered_by_state,
+    })
+    return metadata
+
+
 def _mcp_gateway_summary_row(row: AwoooPMcpGatewayAudit) -> dict[str, Any]:
     """Convert SQLAlchemy audit rows into the truth-chain summary shape."""
     return {
@@ -971,8 +1054,10 @@ async def get_run_detail(
         for row in inbound_events
     ]
 
-    outbound_items = [
-        {
+    outbound_items = []
+    for row in outbound_messages:
+        callback_reply = _outbound_callback_reply(row.source_envelope)
+        outbound_items.append({
             "message_id": row.message_id,
             "channel_type": row.channel_type,
             "message_type": row.message_type,
@@ -983,9 +1068,8 @@ async def get_run_detail(
             "queued_at": row.queued_at,
             "sent_at": row.sent_at,
             "triggered_by_state": row.triggered_by_state,
-        }
-        for row in outbound_messages
-    ]
+            "callback_reply": callback_reply,
+        })
 
     def _mcp_item(row: AwoooPMcpGatewayAudit) -> dict[str, Any]:
         gate_result = row.gate_result if isinstance(row.gate_result, dict) else {}
@@ -1136,6 +1220,7 @@ async def get_run_detail(
             )
         )
     for row in outbound_messages:
+        callback_reply = _outbound_callback_reply(row.source_envelope)
         timeline.append(
             _timeline_item(
                 ts=row.sent_at or row.queued_at,
@@ -1144,14 +1229,15 @@ async def get_run_detail(
                     row.channel_type,
                     row.message_type,
                     row.content_preview,
+                    callback_reply,
                 ),
-                status=row.send_status,
-                summary=row.content_preview or row.send_error,
-                metadata={
-                    "message_type": row.message_type,
-                    "provider_message_id": row.provider_message_id,
-                    "triggered_by_state": row.triggered_by_state,
-                },
+                status=_outbound_timeline_status(row.send_status, callback_reply),
+                summary=_outbound_timeline_summary(
+                    content_preview=row.content_preview,
+                    send_error=row.send_error,
+                    callback_reply=callback_reply,
+                ),
+                metadata=_outbound_timeline_metadata(row, callback_reply),
             )
         )
     if run.completed_at:
diff --git a/apps/api/tests/test_awooop_operator_timeline_labels.py b/apps/api/tests/test_awooop_operator_timeline_labels.py
index 50c3ce46..250bbb57 100644
--- a/apps/api/tests/test_awooop_operator_timeline_labels.py
+++ b/apps/api/tests/test_awooop_operator_timeline_labels.py
@@ -7,6 +7,8 @@ from src.services.platform_operator_service import (
     _legacy_mcp_timeline_summary,
     _list_filter_context_limit,
     _outbound_timeline_title,
+    _outbound_timeline_status,
+    _outbound_timeline_summary,
     _remediation_summary_matches_incident_id,
     _remediation_summary_matches_status,
     _remediation_timeline_summary,
@@ -61,6 +63,54 @@ def test_outbound_timeline_title_falls_back_to_human_label() -> None:
     assert title == "TELEGRAM：漸進式狀態回饋"
 
 
+def test_outbound_timeline_title_labels_callback_reply_fallback() -> None:
+    callback_reply = {
+        "status": "callback_reply_fallback_sent",
+        "action": "history",
+        "incident_id": "INC-20260513-79ED5E",
+        "parse_mode": "plain_text",
+    }
+
+    title = _outbound_timeline_title(
+        "telegram",
+        "final",
+        "事件歷史統計 INC-20260513-79ED5E",
+        callback_reply,
+    )
+    summary = _outbound_timeline_summary(
+        content_preview="事件歷史統計 INC-20260513-79ED5E",
+        send_error=None,
+        callback_reply=callback_reply,
+    )
+
+    assert title == "TELEGRAM：歷史回覆 fallback 已送出"
+    assert _outbound_timeline_status("sent", callback_reply) == (
+        "callback_reply_fallback_sent"
+    )
+    assert "callback=history" in summary
+    assert "incident=INC-20260513-79ED5E" in summary
+    assert "parse_mode=plain_text" in summary
+
+
+def test_outbound_timeline_title_labels_callback_reply_failure() -> None:
+    callback_reply = {
+        "status": "callback_reply_failed",
+        "action": "detail",
+        "incident_id": "INC-20260513-79ED5E",
+        "error": "HTTP error: 400",
+    }
+
+    assert _outbound_timeline_title("telegram", "error", None, callback_reply) == (
+        "TELEGRAM：詳情回覆送出失敗"
+    )
+    assert _outbound_timeline_status("failed", callback_reply) == "callback_reply_failed"
+    assert "error=HTTP error: 400" in _outbound_timeline_summary(
+        content_preview=None,
+        send_error="HTTP error: 400",
+        callback_reply=callback_reply,
+    )
+
+
 def test_collect_run_incident_ids_reads_source_refs_and_legacy_text() -> None:
     run = SimpleNamespace(
         trigger_ref="not-an-incident",
diff --git a/apps/web/messages/en.json b/apps/web/messages/en.json
index c15ee00c..42b97165 100644
--- a/apps/web/messages/en.json
+++ b/apps/web/messages/en.json
@@ -2034,6 +2034,10 @@
         "received": "Received",
         "running": "Running",
         "sent": "Sent",
+        "callbackReplySent": "Callback sent",
+        "callbackReplyFallbackSent": "Callback fallback",
+        "callbackReplyRescueSent": "Callback rescue",
+        "callbackReplyFailed": "Callback failed",
         "shadow": "Shadow",
         "success": "Success",
         "timeout": "Timed out",
diff --git a/apps/web/messages/zh-TW.json b/apps/web/messages/zh-TW.json
index 580c0013..100a0772 100644
--- a/apps/web/messages/zh-TW.json
+++ b/apps/web/messages/zh-TW.json
@@ -2035,6 +2035,10 @@
         "received": "已接收",
         "running": "執行中",
         "sent": "已送出",
+        "callbackReplySent": "Callback 已送出",
+        "callbackReplyFallbackSent": "Callback fallback",
+        "callbackReplyRescueSent": "Callback 救援",
+        "callbackReplyFailed": "Callback 失敗",
         "shadow": "Shadow",
         "success": "成功",
         "timeout": "已超時",
diff --git a/apps/web/src/app/[locale]/awooop/runs/[run_id]/page.tsx b/apps/web/src/app/[locale]/awooop/runs/[run_id]/page.tsx
index 3aecd97b..74910ae5 100644
--- a/apps/web/src/app/[locale]/awooop/runs/[run_id]/page.tsx
+++ b/apps/web/src/app/[locale]/awooop/runs/[run_id]/page.tsx
@@ -213,6 +213,10 @@ const STATUS_STYLE: Record<string, string> = {
   completed: "border-[#9bc7a4] bg-[#f0faf2] text-[#17602a]",
   success: "border-[#9bc7a4] bg-[#f0faf2] text-[#17602a]",
   sent: "border-[#9bc7a4] bg-[#f0faf2] text-[#17602a]",
+  callback_reply_sent: "border-[#9bc7a4] bg-[#f0faf2] text-[#17602a]",
+  callback_reply_fallback_sent: "border-[#d9b36f] bg-[#fff7e8] text-[#8a5a08]",
+  callback_reply_rescue_sent: "border-[#d9b36f] bg-[#fff7e8] text-[#8a5a08]",
+  callback_reply_failed: "border-[#e2a29b] bg-[#fff0ef] text-[#9f2f25]",
   running: "border-[#9bb6d9] bg-[#eef5ff] text-[#1f5b9b]",
   received: "border-[#9bb6d9] bg-[#eef5ff] text-[#1f5b9b]",
   waiting_approval: "border-[#d9b36f] bg-[#fff7e8] text-[#8a5a08]",
@@ -236,6 +240,10 @@ const STATUS_TRANSLATION_KEYS: Record<string, string> = {
   received: "statuses.received",
   running: "statuses.running",
   sent: "statuses.sent",
+  callback_reply_sent: "statuses.callbackReplySent",
+  callback_reply_fallback_sent: "statuses.callbackReplyFallbackSent",
+  callback_reply_rescue_sent: "statuses.callbackReplyRescueSent",
+  callback_reply_failed: "statuses.callbackReplyFailed",
   shadow: "statuses.shadow",
   success: "statuses.success",
   timeout: "statuses.timeout",