diff --git a/hermes_cli/update_cmd_fleet.py b/hermes_cli/update_cmd_fleet.py
index e9f1c92875..b8ebab13f3 100644
--- a/hermes_cli/update_cmd_fleet.py
+++ b/hermes_cli/update_cmd_fleet.py
@@ -78,14 +78,27 @@ def _current_checkout_sha() -> str | None:
 
 
 def _receipt_looks_unfinished(receipt: dict) -> bool:
-    """True when *receipt* is from an update that did not finish cleanly."""
+    """True when *receipt* is from an update that did not finish cleanly.
+
+    ``stop_reason`` records *how* the command boundary closed the receipt
+    (``completed at command boundary``, ``sys.exit(0)``, even KeyboardInterrupt
+    on an otherwise successful run). A truthy stop_reason must not make a
+    successful receipt look unfinished, or the next ``hermes update`` retriggers
+    ``fleet_restart_pending`` from pre-pull plan SHAs.
+    """
+    exit_code = receipt.get("exit_code")
+    outcome = receipt.get("outcome")
+    if exit_code not in (0, None):
+        return True
+    if outcome in ("failed", "partial", "running"):
+        return True
     gateway_restart = receipt.get("gateway_restart")
-    return bool(
-        receipt.get("stop_reason")
-        or receipt.get("exit_code") not in (0, None)
-        or receipt.get("outcome") in ("failed", "partial", "running")
-        or (isinstance(gateway_restart, dict) and gateway_restart.get("incomplete"))
-    )
+    if isinstance(gateway_restart, dict) and gateway_restart.get("incomplete"):
+        return True
+    stop_reason = receipt.get("stop_reason")
+    if stop_reason and outcome != "success" and exit_code != 0:
+        return True
+    return False
 
 
 def _receipt_reports_stale_runtime(expected_sha: str | None = None) -> bool:
diff --git a/tests/hermes_cli/test_update_fleet_restart_pending.py b/tests/hermes_cli/test_update_fleet_restart_pending.py
index 156573a92e..49fcf3705b 100644
--- a/tests/hermes_cli/test_update_fleet_restart_pending.py
+++ b/tests/hermes_cli/test_update_fleet_restart_pending.py
@@ -254,6 +254,67 @@ def test_successful_receipt_with_pre_update_plan_shas_does_not_retrigger(
     assert update_cmd._pending_fleet_restart_needed() is False
 
 
+def test_successful_command_boundary_receipt_without_fleet_does_not_retrigger(
+    monkeypatch,
+):
+    """A normal command-boundary stop is not an interrupted update."""
+    disk_sha = "n" * 40
+    old_sha = "o" * 40
+    monkeypatch.setattr(update_cmd, "_current_checkout_sha", lambda: disk_sha)
+    monkeypatch.setattr(update_cmd_fleet, "_current_checkout_sha", lambda: disk_sha)
+
+    receipt_dir = get_hermes_home() / "logs" / "update_receipts"
+    receipt_dir.mkdir(parents=True)
+    (receipt_dir / "latest.json").write_text(
+        json.dumps(
+            {
+                "exit_code": 0,
+                "outcome": "success",
+                "stop_reason": "completed at command boundary",
+                "plan": {
+                    "expected_sha": old_sha,
+                    "runtimes": [
+                        {
+                            "kind": "gateway",
+                            "profile": "default",
+                            "pid": 1,
+                            "code_sha": old_sha,
+                        }
+                    ],
+                },
+                "fleet": [],
+                "gateway_restart": {},
+            }
+        ),
+        encoding="utf-8",
+    )
+
+    assert update_cmd._pending_fleet_restart_needed() is False
+
+
+@pytest.mark.parametrize(
+    "receipt",
+    [
+        {"outcome": "success", "exit_code": 0, "stop_reason": "sys.exit(0)"},
+        {"outcome": "success", "stop_reason": "KeyboardInterrupt: "},
+        {"exit_code": 0, "stop_reason": "sys.exit(0)"},
+    ],
+)
+def test_successful_non_boundary_stop_reasons_are_finished(receipt):
+    """Successful sys.exit(0)/KeyboardInterrupt must not look unfinished."""
+    assert update_cmd._receipt_looks_unfinished(receipt) is False
+
+
+def test_failed_interrupt_stop_reason_is_unfinished():
+    assert update_cmd._receipt_looks_unfinished(
+        {
+            "outcome": "failed",
+            "exit_code": 1,
+            "stop_reason": "KeyboardInterrupt: ",
+        }
+    ) is True
+
+
 def test_stale_fleet_matrix_on_latest_receipt_is_pending(monkeypatch):
     disk_sha = "n" * 40
     monkeypatch.setattr(update_cmd, "_current_checkout_sha", lambda: disk_sha)