diff --git a/hermes_logging.py b/hermes_logging.py
index 0ebc450a22..8d16e653c7 100644
--- a/hermes_logging.py
+++ b/hermes_logging.py
@@ -195,10 +195,6 @@ def setup_logging(
         The ``logs/`` directory where files are written.
     """
     global _logging_initialized
-    if _logging_initialized and not force:
-        home = hermes_home or get_hermes_home()
-        return home / "logs"
-
     home = hermes_home or get_hermes_home()
     log_dir = home / "logs"
     log_dir.mkdir(parents=True, exist_ok=True)
@@ -248,6 +244,9 @@ def setup_logging(
             log_filter=_ComponentFilter(COMPONENT_PREFIXES["gateway"]),
         )
 
+    if _logging_initialized and not force:
+        return log_dir
+
     # Ensure root logger level is low enough for the handlers to fire.
     if root.level == logging.NOTSET or root.level > level:
         root.setLevel(level)
diff --git a/tests/test_hermes_logging.py b/tests/test_hermes_logging.py
index 586a4d6666..c4168f79b9 100644
--- a/tests/test_hermes_logging.py
+++ b/tests/test_hermes_logging.py
@@ -261,6 +261,42 @@ class TestGatewayMode:
         ]
         assert len(gw_handlers) == 0
 
+    def test_gateway_log_created_after_cli_init(self, hermes_home):
+        """Gateway mode attaches gateway.log even after earlier CLI init."""
+        hermes_logging.setup_logging(hermes_home=hermes_home, mode="cli")
+        hermes_logging.setup_logging(hermes_home=hermes_home, mode="gateway")
+
+        root = logging.getLogger()
+        gw_handlers = [
+            h for h in root.handlers
+            if isinstance(h, RotatingFileHandler)
+            and "gateway.log" in getattr(h, "baseFilename", "")
+        ]
+        assert len(gw_handlers) == 1
+
+        logging.getLogger("gateway.run").info("gateway connected after cli init")
+
+        for h in root.handlers:
+            h.flush()
+
+        gw_log = hermes_home / "logs" / "gateway.log"
+        assert gw_log.exists()
+        assert "gateway connected after cli init" in gw_log.read_text()
+
+    def test_gateway_log_created_after_cli_init_without_duplicate_handlers(self, hermes_home):
+        """Repeated gateway setup calls do not attach duplicate gateway handlers."""
+        hermes_logging.setup_logging(hermes_home=hermes_home, mode="cli")
+        hermes_logging.setup_logging(hermes_home=hermes_home, mode="gateway")
+        hermes_logging.setup_logging(hermes_home=hermes_home, mode="gateway")
+
+        root = logging.getLogger()
+        gw_handlers = [
+            h for h in root.handlers
+            if isinstance(h, RotatingFileHandler)
+            and "gateway.log" in getattr(h, "baseFilename", "")
+        ]
+        assert len(gw_handlers) == 1
+
     def test_gateway_log_receives_gateway_records(self, hermes_home):
         """gateway.log captures records from gateway.* loggers."""
         hermes_logging.setup_logging(hermes_home=hermes_home, mode="gateway")