diff --git a/tests/tools/test_bot_mode_dm.py b/tests/tools/test_bot_mode_dm.py
index 755ea800a6..963a294814 100644
--- a/tests/tools/test_bot_mode_dm.py
+++ b/tests/tools/test_bot_mode_dm.py
@@ -976,3 +976,48 @@ def test_settled_live_wait_unlinks_the_intent_but_a_pending_one_keeps_it(tmp_pat
     assert bot_mode_dm._wait_live_dm(str(tmp_path), "d1", dm_file=dm_file) == 0
     assert not intent.exists()
     assert not dm_file.exists(), "the dm .txt holds the same plaintext as the settled intent"
+
+
+def test_pending_approval_spawn_names_the_approval_and_reclaims_the_dm_file(tmp_path, monkeypatch):
+    """terminal_tool's approval gate answers pending_approval with an EMPTY error and no session_id;
+    a local delivery must say the runner needs approval (nothing was sent), not blame the spawn."""
+    dm_file = tmp_path / "message.txt"
+    dm_file.write_text("secret", encoding="utf-8")
+    import tools.terminal_tool as terminal_tool_module
+
+    pending = terminal_tool_module._error_json("", status="pending_approval", approval_pending=True,
+                                               command="python3 runner", description="command flagged")
+    monkeypatch.setattr(terminal_tool_module, "terminal_tool", lambda command, **kwargs: pending)
+
+    result = json.loads(bot_mode_dm._spawn_delivery("unused", "@researcher", dm_file=str(dm_file),
+                                                    task_id=None, agent=None))
+
+    assert "approval" in result["error"] and "nothing was sent" in result["error"]
+    assert "no process id" not in result["error"]
+    assert not dm_file.exists()
+
+
+def test_relay_waiter_that_cannot_start_reports_queued_not_failed(tmp_path, monkeypatch):
+    """The relay envelope is queued before the reply waiter spawns and the Desktop drains it on its
+    own: a waiter that cannot start is a lost wake-up, not a failed delivery (a hard error makes the
+    sender resend and deliver twice)."""
+    from tools import bot_relay
+
+    root = tmp_path / ".hermes"
+    (root / "profiles" / "default").mkdir(parents=True)
+    bot_relay.write_remote_roster(root, [{"profile": "researcher", "handle": "researcher",
+                                          "connection_id": "laptop-1", "connection_label": "laptop"}])
+    import tools.terminal_tool as terminal_tool_module
+
+    pending = terminal_tool_module._error_json("", status="pending_approval", approval_pending=True,
+                                               command="python3 waiter", description="command flagged")
+    monkeypatch.setattr(terminal_tool_module, "terminal_tool", lambda command, **kwargs: pending)
+
+    result = json.loads(bot_mode_dm._try_relay_delivery(root, "researcher", "hello", "default",
+                                                        task_id=None, agent=None))
+
+    assert result["status"] == "queued"
+    assert "error" not in result
+    assert "Do NOT resend" in result["detail"]
+    assert "approval" in result["notification_error"]
+    assert list((bot_relay.relay_root(root) / bot_relay.OUTBOX_DIR).glob("*.json")), "envelope still queued"
diff --git a/tools/bot_mode_dm.py b/tools/bot_mode_dm.py
index a1f8dee179..6bd9ebd62d 100644
--- a/tools/bot_mode_dm.py
+++ b/tools/bot_mode_dm.py
@@ -289,7 +289,19 @@ def _try_relay_delivery(root: Path, raw_target: str, content: str, me: str, *,
             # per the #93091 reason enum).
             return json.dumps({"error": str(exc), "reason": exc.reason})
         label = f"@{match['handle']} on {match['connection_label'] or match['connection_id']}"
-        return _spawn_delivery(waiter_command(root, envelope), label, task_id=task_id, agent=agent)
+        raw = _spawn_delivery(waiter_command(root, envelope), label, task_id=task_id, agent=agent)
+        waiter_error = json.loads(raw).get("error")
+        if not waiter_error:
+            return raw
+        # The envelope is already queued and the Desktop drains it on its own, so a waiter that
+        # failed to start loses only the reply wake-up. Reporting a hard failure here makes the
+        # sender resend and deliver the message twice. Same shape as the live-owner branch of
+        # _start_delivery: queued + notification_error.
+        return json.dumps({
+            "status": "queued", "to": label, "notification_error": waiter_error,
+            "detail": (f"Message queued for {label}; the relay delivers it on its own, but the reply "
+                       "waiter did not start, so the reply will NOT wake you. Do NOT resend."),
+        })
     except Exception:
         logger.debug("relay delivery attempt failed", exc_info=True)
         return None
@@ -602,6 +614,12 @@ def _spawn_delivery(command: str, label: str, *, dm_file: Optional[str] = None,
         proc_id = parsed.get("session_id") or ""
         if parsed.get("error"):
             return _err(f"Delivery to {label} failed to start: {parsed['error']}")
+        if parsed.get("status") == "pending_approval":
+            # terminal_tool's approval gate answers with an EMPTY error and no session_id: the runner
+            # never launched because nobody in this turn could approve its command.
+            return _err(f"Delivery to {label} failed to start: its command needs terminal approval that nobody "
+                        "in this turn can grant" + (", so nothing was sent. Approve it (or add it to "
+                                                    "command_allowlist) and send again." if dm_file else "."))
         if not proc_id:
             return _err(f"Delivery to {label} failed to start: no process id returned")
         # From here the background runner owns the file (removed after the consumer finishes).