diff --git a/requirements/tox-py39-cp39-win32-amd64.txt b/requirements/tox-py39-cp39-win32-amd64.txt
index e8bf54cfcd..112ee633a5 100644
--- a/requirements/tox-py39-cp39-win32-amd64.txt
+++ b/requirements/tox-py39-cp39-win32-amd64.txt
@@ -6,11 +6,11 @@
 #
 atomicwrites==1.4.1
     # via pytest
-attrs==22.2.0
+attrs==23.1.0
     # via pytest
 autocommand==2.2.2
     # via jaraco-text
-certifi==2022.12.7
+certifi==2023.5.7
     # via requests
 cffi==1.15.1
     # via cryptography
@@ -22,11 +22,11 @@ colorama==0.4.6
     # via
     #   pytest
     #   pytest-watch
-coverage==7.2.2
+coverage==7.2.7
     # via
     #   -r requirements/tox-py39-cp39-win32-amd64.in
     #   pytest-cov
-cryptography==40.0.1
+cryptography==41.0.1
     # via
     #   pyopenssl
     #   trustme
@@ -38,7 +38,7 @@ idna==3.4
     # via
     #   requests
     #   trustme
-inflect==6.0.2
+inflect==6.0.4
     # via jaraco-text
 iniconfig==2.0.0
     # via pytest
@@ -46,14 +46,14 @@ jaraco-context==4.3.0
     # via
     #   -r requirements/tox-py39-cp39-win32-amd64.in
     #   jaraco-text
-jaraco-functools==3.6.0
+jaraco-functools==3.7.0
     # via
     #   cheroot (setup.cfg)
     #   jaraco-text
     #   tempora
 jaraco-text==3.11.1
     # via -r requirements/tox-py39-cp39-win32-amd64.in
-markdown-it-py==2.2.0
+markdown-it-py==3.0.0
     # via rich
 mdurl==0.1.2
     # via markdown-it-py
@@ -62,7 +62,7 @@ more-itertools==9.1.0
     #   cheroot (setup.cfg)
     #   jaraco-functools
     #   jaraco-text
-packaging==23.0
+packaging==23.1
     # via
     #   pytest
     #   pytest-rerunfailures
@@ -79,11 +79,11 @@ py==1.11.0
     #   pytest
 pycparser==2.21
     # via cffi
-pydantic==1.10.7
+pydantic==1.10.9
     # via inflect
-pygments==2.14.0
+pygments==2.15.1
     # via rich
-pyopenssl==23.1.1 ; implementation_name != "pypy"
+pyopenssl==23.2.0 ; implementation_name != "pypy"
     # via -r requirements/tox-py39-cp39-win32-amd64.in
 pypytools==0.6.2
     # via -r requirements/tox-py39-cp39-win32-amd64.in
@@ -101,42 +101,42 @@ pytest-clarity==1.0.1
     # via -r requirements/tox-py39-cp39-win32-amd64.in
 pytest-cov==2.12.0
     # via -r requirements/tox-py39-cp39-win32-amd64.in
-pytest-mock==3.10.0
+pytest-mock==3.11.1
     # via -r requirements/tox-py39-cp39-win32-amd64.in
 pytest-rerunfailures==11.1.2
     # via -r requirements/tox-py39-cp39-win32-amd64.in
-pytest-sugar==0.9.6
+pytest-sugar==0.9.7
     # via -r requirements/tox-py39-cp39-win32-amd64.in
 pytest-watch==4.2.0
     # via -r requirements/tox-py39-cp39-win32-amd64.in
-pytest-xdist==3.2.1
+pytest-xdist==3.3.1
     # via -r requirements/tox-py39-cp39-win32-amd64.in
 pytz==2023.3
     # via tempora
-requests==2.28.2
+requests==2.31.0
     # via
     #   -r requirements/tox-py39-cp39-win32-amd64.in
     #   requests-toolbelt
     #   requests-unixsocket
-requests-toolbelt==0.10.1
+requests-toolbelt==1.0.0
     # via -r requirements/tox-py39-cp39-win32-amd64.in
 requests-unixsocket==0.3.0
     # via -r requirements/tox-py39-cp39-win32-amd64.in
-rich==13.3.3
+rich==13.4.2
     # via pytest-clarity
-tempora==5.2.1
+tempora==5.3.0
     # via portend
-termcolor==2.2.0
+termcolor==2.3.0
     # via pytest-sugar
 toml==0.10.2
     # via pytest
 tomli==2.0.1
     # via coverage
-trustme==0.9.0
+trustme==1.0.0
     # via -r requirements/tox-py39-cp39-win32-amd64.in
-typing-extensions==4.5.0
+typing-extensions==4.6.3
     # via pydantic
-urllib3==1.26.15
+urllib3==2.0.3
     # via requests
 watchdog==3.0.0
     # via pytest-watch