diff --git a/.builders/images/runner_dependencies.txt b/.builders/images/runner_dependencies.txt
index 3e70f6196970f..18295cc266e2e 100644
--- a/.builders/images/runner_dependencies.txt
+++ b/.builders/images/runner_dependencies.txt
@@ -1,5 +1,5 @@
 python-dotenv==1.0.0
-urllib3==2.6.0
+urllib3==2.2.0
 auditwheel==6.0.0; sys_platform == 'linux'
 delvewheel==1.5.2; sys_platform == 'win32'
 delocate==0.13.0; sys_platform == 'darwin'
diff --git a/.github/workflows/pr-all.yml b/.github/workflows/pr-all.yml
index 2a906d6fafd7c..67465b1f88035 100644
--- a/.github/workflows/pr-all.yml
+++ b/.github/workflows/pr-all.yml
@@ -4,8 +4,11 @@ on:
   pull_request:
     paths:
     - datadog_checks_base/datadog_checks/**
+    - datadog_checks_base/pyproject.toml
     - datadog_checks_dev/datadog_checks/dev/*.py
+    - datadog_checks_dev/pyproject.toml
     - ddev/src/**
+    - ddev/pyproject.toml
     - "!agent_requirements.in"
 
 concurrency:
diff --git a/agent_requirements.in b/agent_requirements.in
index 22a1b49fa31f0..85e944b3e8db6 100644
--- a/agent_requirements.in
+++ b/agent_requirements.in
@@ -64,6 +64,6 @@ simplejson==3.20.1
 snowflake-connector-python==3.17.2
 supervisor==4.3.0
 tuf==4.0.0
-urllib3==2.6.0
+urllib3==2.5.0
 vertica-python==1.4.0
 wrapt==1.17.3
diff --git a/datadog_checks_base/changelog.d/22172.added b/datadog_checks_base/changelog.d/22172.added
new file mode 100644
index 0000000000000..957e71c8ed958
--- /dev/null
+++ b/datadog_checks_base/changelog.d/22172.added
@@ -0,0 +1 @@
+Bump urllib3 to version 2.6.2
\ No newline at end of file
diff --git a/datadog_checks_base/pyproject.toml b/datadog_checks_base/pyproject.toml
index b52c148aa760b..f7df545e0fa96 100644
--- a/datadog_checks_base/pyproject.toml
+++ b/datadog_checks_base/pyproject.toml
@@ -50,7 +50,7 @@ deps = [
     "requests-unixsocket2==1.0.0",
     "requests==2.32.5",
     "simplejson==3.20.1",
-    "urllib3==2.6.0",
+    "urllib3==2.5.0",
     "wrapt==1.17.3",
 ]
 http = [