fix(bot-mode): a pending command approval is not a failed DM delivery

terminal_tool's approval gate answers `status: pending_approval` with an
EMPTY `error` (#28323) and no `session_id`, so _spawn_delivery's specific
branch (`if parsed.get("error")`) was skipped and every unanswered
approval fell through to "Delivery to X failed to start: no process id
returned" — blaming the spawn for an approval nobody in a non-interactive
turn (api_server, `hermes peer dm`, cron) could grant.

- _spawn_delivery: the pending shape gets its own message (the runner
  command needs terminal approval nobody in this turn can grant); a
  local/peer DM adds "nothing was sent — approve it or add it to
  command_allowlist and send again". Ownership is never transferred, so
  the existing finally still reclaims the plaintext DM file.
- _try_relay_delivery: the envelope is queued on disk BEFORE the reply
  waiter spawns and the Desktop drains it independently, so ANY waiter
  spawn failure is a lost wake-up, not a failed delivery; reporting it as
  an error made the sender resend and deliver the message twice. The
  relay path now returns the shape _start_delivery's live-owner branch
  already uses (status queued + notification_error + "Do NOT resend")
  instead of inventing a new status value nothing reads.

Slimmer redo of #92971 by @jonpol01 (same diagnosis, same relay/local
split on `dm_file is None`); the source-text contract test and the
`sent_no_reply_wake` status were dropped.

Fixes #111716

Co-authored-by: John Paul Soliva <soliva.johnpaul@icloud.com>

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).