diff --git a/gateway/restart.py b/gateway/restart.py
index 57732284c3..8e31ab713b 100644
--- a/gateway/restart.py
+++ b/gateway/restart.py
@@ -355,7 +355,9 @@ def resolve_systemd_timeout_stop_sec(
     return int(max(_seconds(floor_s), max(drain, cron_budget) + _seconds(headroom_s)))
 
 
-def resolve_restart_exit_wait_budget(drain_timeout: float, after_turn_timeout: float, *, headroom: float = 15.0) -> float:
+def resolve_restart_exit_wait_budget(
+    drain_timeout: float, after_turn_timeout: float, cron_drain_timeout: float = 0.0, *, headroom: float = 15.0,
+) -> float:
     """Seconds a CLI should wait for the gateway PID to exit after SIGUSR1: in-band restart may
-    defer ``stop()`` until turns finish, then spend ``drain_timeout`` inside it — cover both."""
-    return _seconds(drain_timeout) + _seconds(after_turn_timeout) + _seconds(headroom)
+    defer ``stop()`` until turns finish, then spend the longer chat or cron drain inside it."""
+    return max(_seconds(drain_timeout), _seconds(cron_drain_timeout)) + _seconds(after_turn_timeout) + _seconds(headroom)
diff --git a/hermes_cli/gateway.py b/hermes_cli/gateway.py
index a210a213de..1d379af8a5 100644
--- a/hermes_cli/gateway.py
+++ b/hermes_cli/gateway.py
@@ -3561,14 +3561,11 @@ def _get_cron_drain_timeout() -> float:
 def _get_restart_exit_wait_budget() -> float:
     """CLI wait for gateway exit after SIGUSR1 / self-restart (#77184)."""
     return resolve_restart_exit_wait_budget(
-        # TimeoutStopSec must cover the full stop budget, not just restart_drain_timeout. Cron work can
-        # legally wait cron_drain_timeout plus cleanup reserve before interrupt/teardown, and systemd
-        # SIGKILLs if the unit's deadline is shorter (#94759). 30s of post-drain headroom is preserved on
-        # top, with a 60s floor.
         _get_restart_drain_timeout(),
         _agent_timeout_setting(
             "HERMES_RESTART_AFTER_TURN_TIMEOUT", "restart_after_turn_timeout", parse_restart_after_turn_timeout
         ),
+        _get_cron_drain_timeout(),
     )
 
 
diff --git a/hermes_cli/update_receipt.py b/hermes_cli/update_receipt.py
index 65a163398b..c1d6ddf466 100644
--- a/hermes_cli/update_receipt.py
+++ b/hermes_cli/update_receipt.py
@@ -682,8 +682,8 @@ def print_fleet_version_matrix(fleet: list[dict[str, Any]]) -> bool:
             print(f"      {line}")
     if RESTART_PENDING_STATE in states:
         print()
-        print("  ℹ A restart-pending gateway picks up the new code as soon as this update exits;")
-        print("    verify afterwards with `hermes gateway status`.")
+        print("  ℹ A restart-pending gateway has not yet been verified on the new code;")
+        print("    check after this update exits with `hermes gateway status`.")
     stale_or_down = sum(1 for entry in fleet if entry.get("state") in ("stale", "down"))
     if stale_or_down:
         print()
diff --git a/tests/gateway/test_restart_after_turn.py b/tests/gateway/test_restart_after_turn.py
index e0f2e5b1de..dd06e69515 100644
--- a/tests/gateway/test_restart_after_turn.py
+++ b/tests/gateway/test_restart_after_turn.py
@@ -22,9 +22,25 @@ def test_parse_restart_after_turn_timeout_defaults_and_clamps():
 def test_resolve_restart_exit_wait_budget_covers_both_phases():
     assert resolve_restart_exit_wait_budget(0, 0, headroom=15) == 15.0
     assert resolve_restart_exit_wait_budget(180, 21600, headroom=15) == 180 + 21600 + 15
+    assert resolve_restart_exit_wait_budget(2, 3, 80, headroom=15) == 3 + 80 + 15
+    assert resolve_restart_exit_wait_budget(80, 3, 2, headroom=15) == 3 + 80 + 15
+    assert resolve_restart_exit_wait_budget(2, 3, 0, headroom=15) == 3 + 2 + 15
     assert resolve_restart_exit_wait_budget("bad", "bad", headroom="x") == 0.0
 
 
+def test_cli_restart_wait_covers_configured_cron_drain(tmp_path, monkeypatch):
+    import hermes_cli.gateway as gateway_cli
+
+    monkeypatch.setenv("HERMES_HOME", str(tmp_path))
+    for key in ("HERMES_RESTART_DRAIN_TIMEOUT", "HERMES_RESTART_AFTER_TURN_TIMEOUT", "HERMES_CRON_DRAIN_TIMEOUT"):
+        monkeypatch.delenv(key, raising=False)
+    (tmp_path / "config.yaml").write_text(
+        "agent:\n  restart_drain_timeout: 2\n  restart_after_turn_timeout: 3\n  cron_drain_timeout: 80\n",
+        encoding="utf-8",
+    )
+    assert gateway_cli._get_restart_exit_wait_budget() >= 3 + 80 + 15
+
+
 def test_load_restart_after_turn_timeout_preserves_zero(tmp_path, monkeypatch):
     """Config/env ``0`` must disable after-turn wait, not fall back to default."""
     import gateway.run as gateway_run
diff --git a/tests/hermes_cli/test_fleet_matrix_self_restart_pending.py b/tests/hermes_cli/test_fleet_matrix_self_restart_pending.py
index 1a09291130..7ecbaccd92 100644
--- a/tests/hermes_cli/test_fleet_matrix_self_restart_pending.py
+++ b/tests/hermes_cli/test_fleet_matrix_self_restart_pending.py
@@ -55,8 +55,10 @@ def test_ancestor_with_accepted_self_restart_is_pending_while_other_stale_rows_s
     # Without the sibling, the pending row alone is not a failure — and the same pid NOT recorded
     # as pending (the restart phase never reached the ancestor branch) is a plain stale verdict.
     only_ancestor = [row for row in fleet if row["profile"] == "default"]
-    with contextlib.redirect_stdout(io.StringIO()):
+    with contextlib.redirect_stdout(io.StringIO()) as pending_out:
         assert ur.print_fleet_version_matrix(only_ancestor) is False
+    assert "as soon as this update exits" not in pending_out.getvalue()
+    assert "restart pending" in pending_out.getvalue()
     plain = ur.collect_fleet_versions(pre_restart_pids=[ancestor, sibling])
     assert {row["state"] for row in plain} == {"stale"}