diff --git a/doc/source/whatsnew/v2.1.0.rst b/doc/source/whatsnew/v2.1.0.rst
index 44e091e12bfa6..b7cc254d5c7e5 100644
--- a/doc/source/whatsnew/v2.1.0.rst
+++ b/doc/source/whatsnew/v2.1.0.rst
@@ -528,6 +528,7 @@ Period
 - Bug in :class:`PeriodDtype` constructor raising ``ValueError`` instead of ``TypeError`` when an invalid type is passed (:issue:`51790`)
 - Bug in :func:`read_csv` not processing empty strings as a null value, with ``engine="pyarrow"`` (:issue:`52087`)
 - Bug in :func:`read_csv` returning ``object`` dtype columns instead of ``float64`` dtype columns with ``engine="pyarrow"`` for columns that are all null with ``engine="pyarrow"`` (:issue:`52087`)
+- Bug in :meth:`Period.now` not accepting the ``freq`` parameter as a keyword argument (:issue:`53369`)
 - Bug in :meth:`arrays.PeriodArray.map` and :meth:`PeriodIndex.map`, where the supplied callable operated array-wise instead of element-wise (:issue:`51977`)
 - Bug in incorrectly allowing construction of :class:`Period` or :class:`PeriodDtype` with :class:`CustomBusinessDay` freq; use :class:`BusinessDay` instead (:issue:`52534`)
 
diff --git a/pandas/_libs/meson.build b/pandas/_libs/meson.build
index 5e59f15d0d089..f302c649bc7bd 100644
--- a/pandas/_libs/meson.build
+++ b/pandas/_libs/meson.build
@@ -105,7 +105,7 @@ foreach ext_name, ext_dict : libs_sources
     py.extension_module(
         ext_name,
         ext_dict.get('sources'),
-        cython_args: ['--include-dir', meson.current_build_dir()],
+        cython_args: ['--include-dir', meson.current_build_dir(), '-X always_allow_keywords=true'],
         include_directories: [inc_np, inc_pd],
         dependencies: ext_dict.get('deps', ''),
         subdir: 'pandas/_libs',
diff --git a/pandas/_libs/tslibs/meson.build b/pandas/_libs/tslibs/meson.build
index 4a51f8dc1e461..14d2eef46da20 100644
--- a/pandas/_libs/tslibs/meson.build
+++ b/pandas/_libs/tslibs/meson.build
@@ -23,7 +23,7 @@ foreach ext_name, ext_dict : tslibs_sources
     py.extension_module(
         ext_name,
         ext_dict.get('sources'),
-        cython_args: ['--include-dir', meson.current_build_dir()],
+        cython_args: ['--include-dir', meson.current_build_dir(), '-X always_allow_keywords=true'],
         include_directories: [inc_np, inc_pd],
         dependencies: ext_dict.get('deps', ''),
         subdir: 'pandas/_libs/tslibs',
diff --git a/pandas/_libs/window/meson.build b/pandas/_libs/window/meson.build
index 61719a35b2346..b83d8730f9447 100644
--- a/pandas/_libs/window/meson.build
+++ b/pandas/_libs/window/meson.build
@@ -1,6 +1,7 @@
 py.extension_module(
     'aggregations',
     ['aggregations.pyx'],
+    cython_args: ['-X always_allow_keywords=true'],
     include_directories: [inc_np, inc_pd],
     dependencies: [py_dep],
     subdir: 'pandas/_libs/window',
@@ -11,6 +12,7 @@ py.extension_module(
 py.extension_module(
     'indexers',
     ['indexers.pyx'],
+    cython_args: ['-X always_allow_keywords=true'],
     include_directories: [inc_np, inc_pd],
     dependencies: [py_dep],
     subdir: 'pandas/_libs/window',
diff --git a/pandas/tests/scalar/period/test_period.py b/pandas/tests/scalar/period/test_period.py
index d908c641a30c6..1e8c2bce1d90d 100644
--- a/pandas/tests/scalar/period/test_period.py
+++ b/pandas/tests/scalar/period/test_period.py
@@ -72,14 +72,16 @@ def test_construction(self):
         assert i1 != i4
         assert i4 == i5
 
-        i1 = Period.now("Q")
+        i1 = Period.now(freq="Q")
         i2 = Period(datetime.now(), freq="Q")
         i3 = Period.now("q")
 
         assert i1 == i2
         assert i1 == i3
 
-        i1 = Period.now("D")
+        # Pass in freq as a keyword argument sometimes as a test for
+        # https://github.com/pandas-dev/pandas/issues/53369
+        i1 = Period.now(freq="D")
         i2 = Period(datetime.now(), freq="D")
         i3 = Period.now(offsets.Day())
 
diff --git a/setup.py b/setup.py
index e285299cfc05e..b87f81e0d8292 100755
--- a/setup.py
+++ b/setup.py
@@ -376,7 +376,7 @@ def run(self):
 # Note: if not using `cythonize`, coverage can be enabled by
 # pinning `ext.cython_directives = directives` to each ext in extensions.
 # github.com/cython/cython/wiki/enhancements-compilerdirectives#in-setuppy
-directives = {"linetrace": False, "language_level": 3}
+directives = {"linetrace": False, "language_level": 3, "always_allow_keywords": True}
 macros = []
 if linetrace:
     # https://pypkg.com/pypi/pytest-cython/f/tests/example-project/setup.py