diff --git a/graalpython/com.oracle.graal.python.test/src/tox/leftpad/tox.ini b/graalpython/com.oracle.graal.python.test/src/tox/leftpad/tox.ini
index 0915e7d20b..90baa3820c 100644
--- a/graalpython/com.oracle.graal.python.test/src/tox/leftpad/tox.ini
+++ b/graalpython/com.oracle.graal.python.test/src/tox/leftpad/tox.ini
@@ -3,7 +3,7 @@ envlist = graalpy
 
 [testenv]
 deps =
-    pytest==6.0.1
+    pytest==8.4.2
 commands =
     pytest --assert=plain tests {posargs}
 
diff --git a/graalpython/hpy/docs/requirements.txt b/graalpython/hpy/docs/requirements.txt
index c7f929385d..4d5b85f2fa 100644
--- a/graalpython/hpy/docs/requirements.txt
+++ b/graalpython/hpy/docs/requirements.txt
@@ -5,4 +5,4 @@ sphinx-rtd-theme==2.0.0
 sphinx-autobuild==2021.3.14
 sphinx-c-autodoc==1.3.0
 clang==17.0.6
-docutils==0.16  # docutils >= 0.17 fails to render bullet lists :/
+docutils==0.18.1  # Latest release supported by Sphinx 5.0.2
diff --git a/graalpython/hpy/hpy/tools/autogen/__main__.py b/graalpython/hpy/hpy/tools/autogen/__main__.py
index 59cdf04872..aec206741f 100644
--- a/graalpython/hpy/hpy/tools/autogen/__main__.py
+++ b/graalpython/hpy/hpy/tools/autogen/__main__.py
@@ -2,7 +2,8 @@
 Parse public_api.h and generate various stubs around
 """
 import sys
-import py
+from pathlib import Path
+
 import pycparser
 from packaging import version
 
@@ -57,7 +58,7 @@ def main():
     if len(sys.argv) != 2:
         print('Usage: python -m hpy.tools.autogen OUTDIR')
         sys.exit(1)
-    outdir = py.path.local(sys.argv[1])
+    outdir = Path(sys.argv[1])
 
     generate(DEFAULT_GENERATORS, outdir)
 
diff --git a/graalpython/hpy/hpy/tools/autogen/autogenfile.py b/graalpython/hpy/hpy/tools/autogen/autogenfile.py
index d4fddb74c7..c14c74b6dc 100644
--- a/graalpython/hpy/hpy/tools/autogen/autogenfile.py
+++ b/graalpython/hpy/hpy/tools/autogen/autogenfile.py
@@ -11,6 +11,13 @@
 */
 """
 
+
+def resolve_relative_path(root, relative_path):
+    if hasattr(root, 'join'):
+        return root.join(relative_path)
+    return root / relative_path
+
+
 class AutoGenFile:
     LANGUAGE = 'C'
     PATH = None
@@ -27,7 +34,8 @@ def generate(self):
     def write(self, root):
         cls = self.__class__
         clsname = '%s.%s' % (cls.__module__, cls.__name__)
-        with root.join(self.PATH).open('w', encoding='utf-8') as f:
+        target = resolve_relative_path(root, self.PATH)
+        with target.open('w', encoding='utf-8') as f:
             if self.DISCLAIMER is not None:
                 f.write(self.DISCLAIMER.format(clsname=clsname))
                 f.write('\n')
diff --git a/graalpython/hpy/hpy/tools/autogen/doc.py b/graalpython/hpy/hpy/tools/autogen/doc.py
index 9824768866..46f619f874 100644
--- a/graalpython/hpy/hpy/tools/autogen/doc.py
+++ b/graalpython/hpy/hpy/tools/autogen/doc.py
@@ -1,7 +1,7 @@
 import textwrap
 import re
 
-from .autogenfile import AutoGenFile
+from .autogenfile import AutoGenFile, resolve_relative_path
 from .parse import toC
 from .ctx import autogen_ctx_h
 from .conf import (DOC_C_API_PAGES_SPECIAL_CASES,
@@ -64,7 +64,8 @@ def write(self, root):
         if not self.BEGIN_MARKER or not self.END_MARKER:
             raise RuntimeError("missing BEGIN_MARKER or END_MARKER")
         n_begin = len(self.BEGIN_MARKER)
-        with root.join(self.PATH).open('r', encoding='utf-8') as f:
+        target = resolve_relative_path(root, self.PATH)
+        with target.open('r', encoding='utf-8') as f:
             content = f.read()
         start = content.find(self.BEGIN_MARKER)
         if start < 0:
@@ -75,7 +76,7 @@ def write(self, root):
             raise RuntimeError(f'end marker "{self.END_MARKER}" not found in'
                                f'file {self.PATH}')
         new_content = self.generate(content[(start+n_begin):end])
-        with root.join(self.PATH).open('w', encoding='utf-8') as f:
+        with target.open('w', encoding='utf-8') as f:
             f.write(content[:start + n_begin] + new_content + content[end:])
 
 
diff --git a/graalpython/hpy/hpy/tools/autogen/parse.py b/graalpython/hpy/hpy/tools/autogen/parse.py
index 6615eb1d50..578317b458 100644
--- a/graalpython/hpy/hpy/tools/autogen/parse.py
+++ b/graalpython/hpy/hpy/tools/autogen/parse.py
@@ -2,17 +2,17 @@
 import sys
 import attr
 import re
-import py
 import pycparser
 import shutil
+from pathlib import Path
 from pycparser import c_ast
 from pycparser.c_generator import CGenerator
 from sysconfig import get_config_var
 from .conf import SPECIAL_CASES, RETURN_CONSTANT
 
-PUBLIC_API_H = py.path.local(__file__).dirpath('public_api.h')
-CURRENT_DIR = py.path.local(__file__).dirpath()
-AUTOGEN_H = py.path.local(__file__).dirpath('autogen.h')
+CURRENT_DIR = Path(__file__).resolve().parent
+PUBLIC_API_H = CURRENT_DIR / 'public_api.h'
+AUTOGEN_H = CURRENT_DIR / 'autogen.h'
 
 
 def toC(node):
@@ -209,13 +209,13 @@ def __init__(self, filename):
         elif sys.platform == 'win32':
             cpp_cmd = [shutil.which("cl.exe")]
         if sys.platform == 'win32':
-            cpp_cmd += ['/E', '/I%s' % CURRENT_DIR]
+            cpp_cmd += ['/E', '/I%s' % str(CURRENT_DIR)]
         else:
-            cpp_cmd += ['-E', '-I%s' % CURRENT_DIR]
+            cpp_cmd += ['-E', '-I%s' % str(CURRENT_DIR)]
 
         msvc = "cl.exe" in cpp_cmd[0].casefold()
 
-        csource = pycparser.preprocess_file(filename,
+        csource = pycparser.preprocess_file(str(filename),
                                   cpp_path=str(cpp_cmd[0]),
                                   cpp_args=cpp_cmd[1:])
 
diff --git a/graalpython/hpy/hpy/tools/autogen/testing/test_autogen.py b/graalpython/hpy/hpy/tools/autogen/testing/test_autogen.py
index 2e1a971d63..28421d1196 100644
--- a/graalpython/hpy/hpy/tools/autogen/testing/test_autogen.py
+++ b/graalpython/hpy/hpy/tools/autogen/testing/test_autogen.py
@@ -1,6 +1,5 @@
 import textwrap
 import difflib
-import py
 import pytest
 from hpy.tools.autogen.parse import HPyAPI
 from hpy.tools.autogen.ctx import autogen_ctx_h, autogen_ctx_def_h
@@ -26,11 +25,11 @@ def src_equal(exp, got):
 class BaseTestAutogen:
 
     @pytest.fixture
-    def initargs(self, tmpdir):
-        self.tmpdir = tmpdir
+    def initargs(self, tmp_path):
+        self.tmpdir = tmp_path
 
     def parse(self, src):
-        fname = self.tmpdir.join('test_api.h')
+        fname = self.tmpdir / 'test_api.h'
         # automatically add useful typedefs
         src = """
             #define STRINGIFY(X) #X
@@ -39,7 +38,7 @@ def parse(self, src):
             typedef int HPy;
             typedef int HPyContext;
         """ + src
-        fname.write(src)
+        fname.write_text(src)
         return HPyAPI.parse(fname)
 
 
diff --git a/graalpython/hpy/requirements-autogen.txt b/graalpython/hpy/requirements-autogen.txt
index 8c9e2a7384..320fc259c8 100644
--- a/graalpython/hpy/requirements-autogen.txt
+++ b/graalpython/hpy/requirements-autogen.txt
@@ -1,4 +1,3 @@
 pycparser==2.21
-py==1.11.0
-packaging==19.2
-attrs==19.3.0
+packaging==25.0
+attrs==23.2.0
diff --git a/mx.graalpython/mx_graalpython.py b/mx.graalpython/mx_graalpython.py
index 15dd3d3116..88bb301f28 100644
--- a/mx.graalpython/mx_graalpython.py
+++ b/mx.graalpython/mx_graalpython.py
@@ -1876,7 +1876,6 @@ def tox_example(args=None):
         "packaging==25.0",
         "platformdirs==4.3.8",
         "pluggy==1.5.0",
-        "py==1.11.0",
         "pyparsing==3.2.3",
         "six==1.17.0",
         "toml==0.10.2",