diff --git a/parallel_web_tools/cli/commands.py b/parallel_web_tools/cli/commands.py
index 0e4eabe..542937c 100644
--- a/parallel_web_tools/cli/commands.py
+++ b/parallel_web_tools/cli/commands.py
@@ -81,6 +81,25 @@
         # CLI extras not installed (pyyaml, questionary)
         pass
 
+
+def _make_output_streams_unicode_safe() -> None:
+    """Prevent UnicodeEncodeError crashes on legacy consoles (e.g. Windows cp1252).
+
+    Help text and other CLI output can contain non-ASCII characters (arrows,
+    box-drawing characters). On consoles using legacy code pages these cannot
+    be encoded, which would crash instead of printing. Reconfigure the streams
+    so unencodable characters are replaced with escape sequences instead.
+    """
+    for stream in (sys.stdout, sys.stderr):
+        if stream is not None and hasattr(stream, "reconfigure"):
+            try:
+                stream.reconfigure(errors="backslashreplace")
+            except Exception:  # noqa: BLE001 - never fail startup over this
+                pass
+
+
+_make_output_streams_unicode_safe()
+
 logging.basicConfig(format="%(asctime)s - %(levelname)s - %(message)s", level=logging.INFO)
 logger = logging.getLogger(__name__)
 
diff --git a/tests/test_cli.py b/tests/test_cli.py
index b4c37f2..2def037 100644
--- a/tests/test_cli.py
+++ b/tests/test_cli.py
@@ -2984,3 +2984,24 @@ def test_service_api_error_exits_api_error(self, runner):
 
         assert result.exit_code == EXIT_API_ERROR
         assert "Balance API error" in result.output
+
+
+class TestUnicodeSafeStreams:
+    """Output streams must not crash on unencodable characters (e.g. Windows cp1252)."""
+
+    def test_helper_replaces_unencodable_characters(self):
+        import io
+
+        from parallel_web_tools.cli.commands import _make_output_streams_unicode_safe
+
+        raw = io.BytesIO()
+        stream = io.TextIOWrapper(raw, encoding="cp1252", errors="strict")
+        with mock.patch("sys.stdout", stream):
+            # Before the fix this raises UnicodeEncodeError on cp1252.
+            _make_output_streams_unicode_safe()
+            print("arrow -> \u2192")
+            stream.flush()
+
+        output = raw.getvalue().decode("cp1252")
+        assert "\u2192" not in output  # cannot be encoded in cp1252
+        assert "arrow" in output  # text itself still printed