diff --git a/tests/test_cli_ui.py b/tests/test_cli_ui.py
index 658b7ea42b..e31a00ab3c 100644
--- a/tests/test_cli_ui.py
+++ b/tests/test_cli_ui.py
@@ -1,11 +1,19 @@
 import pytest
 import shutil
 import os
+import sys
 from tests.utils import http
 
-NAKED_HELP_MESSAGE = """\
+
+if sys.version_info >= (3, 9):
+    REQUEST_ITEM_MSG = "[REQUEST_ITEM ...]"
+else:
+    REQUEST_ITEM_MSG = "[REQUEST_ITEM [REQUEST_ITEM ...]]"
+
+
+NAKED_HELP_MESSAGE = f"""\
 usage:
-    http [METHOD] URL [REQUEST_ITEM ...]
+    http [METHOD] URL {REQUEST_ITEM_MSG}
 
 error:
     the following arguments are required: URL
@@ -13,9 +21,9 @@
 For more information try with --help or visit the https://pie.co/docs
 """
 
-NAKED_HELP_MESSAGE_PRETTY_WITH_NO_ARG = """\
+NAKED_HELP_MESSAGE_PRETTY_WITH_NO_ARG = f"""\
 usage:
-    http [--pretty {all,colors,format,none}] [METHOD] URL [REQUEST_ITEM ...]
+    http [--pretty {{all,colors,format,none}}] [METHOD] URL {REQUEST_ITEM_MSG}
 
 error:
     argument --pretty: expected one argument
@@ -23,9 +31,9 @@
 For more information try with --help or visit the https://pie.co/docs
 """
 
-NAKED_HELP_MESSAGE_PRETTY_WITH_INVALID_ARG = """\
+NAKED_HELP_MESSAGE_PRETTY_WITH_INVALID_ARG = f"""\
 usage:
-    http [--pretty {all,colors,format,none}] [METHOD] URL [REQUEST_ITEM ...]
+    http [--pretty {{all,colors,format,none}}] [METHOD] URL {REQUEST_ITEM_MSG}
 
 error:
     argument --pretty: invalid choice: '$invalid' (choose from 'all', 'colors', 'format', 'none')
@@ -49,15 +57,17 @@ def ignore_terminal_size(monkeypatch):
     def fake_terminal_size(*args, **kwargs):
         return os.terminal_size(PREDEFINED_TERMINAL_SIZE)
 
-    monkeypatch.setattr(shutil, "get_terminal_size", fake_terminal_size)
+    # Setting COLUMNS as an env var is required for 3.8<
+    monkeypatch.setitem(os.environ, 'COLUMNS', str(PREDEFINED_TERMINAL_SIZE[0]))
+    monkeypatch.setattr(shutil, 'get_terminal_size', fake_terminal_size)
 
 
 @pytest.mark.parametrize(
-    "args, expected_msg", [
+    'args, expected_msg', [
         ([], NAKED_HELP_MESSAGE),
-        (["--pretty"], NAKED_HELP_MESSAGE_PRETTY_WITH_NO_ARG),
-        (["pie.dev", "--pretty"], NAKED_HELP_MESSAGE_PRETTY_WITH_NO_ARG),
-        (["--pretty", "$invalid"], NAKED_HELP_MESSAGE_PRETTY_WITH_INVALID_ARG),
+        (['--pretty'], NAKED_HELP_MESSAGE_PRETTY_WITH_NO_ARG),
+        (['pie.dev', '--pretty'], NAKED_HELP_MESSAGE_PRETTY_WITH_NO_ARG),
+        (['--pretty', '$invalid'], NAKED_HELP_MESSAGE_PRETTY_WITH_INVALID_ARG),
     ]
 )
 def test_naked_invocation(ignore_terminal_size, args, expected_msg):