diff --git a/constraints-oldest.txt b/constraints-oldest.txt
index 70d16afb2..75dfb660b 100644
--- a/constraints-oldest.txt
+++ b/constraints-oldest.txt
@@ -3,22 +3,22 @@
 # still works against oldest supported versions of both the Python
 # interpreter and Python ependencies. Keep this up-to-date with minimum
 # versions in `setup.cfg`.
-black==22.3.0
+black==24.10.0
 darkgraylib==2.0.1
 defusedxml==0.7.1
-flake8-2020==1.6.1
-flake8-bugbear==22.1.11
-flake8-comprehensions==3.7.0
-flynt==0.76
-mypy==0.990
-Pygments==2.4.0
-pytest==6.2.0
+flake8-2020==1.8.1
+flake8-bugbear==24.8.19
+flake8-comprehensions==3.16.0
+flynt==1.0.1
+mypy==1.13.0
+Pygments==2.18.0
+pytest==8.3.3
 pytest-kwparametrize==0.0.3
-regex==2021.4.4
-requests_cache==0.7
-ruamel.yaml==0.17.21
-toml==0.10.0
-twine==2.0.0
-types-toml==0.10.4
-typing_extensions==4.0.1
-wheel==0.21.0
+regex==2024.9.11
+requests_cache==1.2.1
+ruamel.yaml==0.18.6
+toml==0.10.2
+twine==5.1.1
+types-toml==0.10.8.20240310
+typing_extensions==4.12.2
+wheel==0.44.0