diff --git a/.github/workflows/docs.yml b/.github/workflows/docs.yml
index 96e6dcbe0..62b1c0577 100644
--- a/.github/workflows/docs.yml
+++ b/.github/workflows/docs.yml
@@ -6,7 +6,7 @@ on:
 jobs:
   test:
     if: "endsWith(github.base_ref, 'main')"
-    runs-on: "ubuntu-20.04"
+    runs-on: "ubuntu-24.04"
     steps:
       - uses: "actions/checkout@v4"
       - uses: "actions/cache@v4"
@@ -19,7 +19,7 @@ jobs:
       - name: "Set up Python"
         uses: "actions/setup-python@v5"
         with:
-          python-version: "3.11"
+          python-version: "3.13"
       - name: "Install Test Dependencies"
         run: |
           pip install -r doc_requirements.txt
@@ -28,7 +28,7 @@ jobs:
           make docs
   no-test:
     if: "!endsWith(github.base_ref, 'main')"
-    runs-on: "ubuntu-20.04"
+    runs-on: "ubuntu-latest"
     steps:
       - run: |
           echo "Skip docs testing on non-main branches."
diff --git a/.github/workflows/lint.yml b/.github/workflows/lint.yml
index 8a6005a51..ec4f4bfb0 100644
--- a/.github/workflows/lint.yml
+++ b/.github/workflows/lint.yml
@@ -12,7 +12,7 @@ jobs:
       matrix:
         python:
           - "3.11"
-          - "3.12"
+          - "3.13"
     steps:
       - uses: "actions/checkout@v4"
       - uses: "actions/cache@v4"
diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index 3543d41ed..87ef298b6 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -12,7 +12,7 @@ env:
 
 jobs:
   unittest:
-    runs-on: "ubuntu-20.04"
+    runs-on: "ubuntu-latest"
     steps:
       - uses: "actions/checkout@v4"
       - uses: "actions/cache@v4"
@@ -37,7 +37,7 @@ jobs:
         run: |
           make unittest
   test:
-    runs-on: "ubuntu-20.04"
+    runs-on: "ubuntu-24.04"
     needs:
       - "unittest"
     strategy:
diff --git a/CHANGES/+click.dependency.bugfix b/CHANGES/+click.dependency.bugfix
new file mode 100644
index 000000000..7089b167f
--- /dev/null
+++ b/CHANGES/+click.dependency.bugfix
@@ -0,0 +1 @@
+Adjust click dependency constraints to breaking changes in y-releases.
diff --git a/lint_requirements.txt b/lint_requirements.txt
index 89de0abfb..f2a2eef9d 100644
--- a/lint_requirements.txt
+++ b/lint_requirements.txt
@@ -1,6 +1,6 @@
 # Lint requirements
 black==25.1.0
-flake8==7.1.2
+flake8==7.2.0
 flake8-pyproject==1.2.3
 isort==6.0.1
 mypy==1.15.0
diff --git a/pulp-glue/pyproject.toml b/pulp-glue/pyproject.toml
index fab8aec63..076ea66c1 100644
--- a/pulp-glue/pyproject.toml
+++ b/pulp-glue/pyproject.toml
@@ -1,5 +1,5 @@
 [build-system]
-requires = ["setuptools<79"]
+requires = ["setuptools<81"]
 build-backend = "setuptools.build_meta"
 
 [project]
@@ -24,8 +24,8 @@ classifiers = [
 ]
 dependencies = [
   "importlib_resources>=5.4.0,<6.2;python_version<'3.9'",
-  "multidict>=6.0.5,<6.4",
-  "packaging>=20.0,<=24.2",  # CalVer
+  "multidict>=6.0.5,<6.5",
+  "packaging>=20.0,<=25.0",  # CalVer
   "requests>=2.24.0,<2.33",
 ]
 
diff --git a/pyproject.toml b/pyproject.toml
index 766330a86..f641e298e 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -1,5 +1,5 @@
 [build-system]
-requires = ["setuptools<79"]
+requires = ["setuptools<81"]
 build-backend = "setuptools.build_meta"
 
 [project]
@@ -24,8 +24,8 @@ classifiers=[
 ]
 dependencies = [
   "pulp-glue==0.32.2.dev",
-  "click>=8.0.0,<9",
-  "packaging>=20.0,<=24.2",  # CalVer
+  "click>=8.0.0,<8.2",  # Proven to not do semver.
+  "packaging>=20.0,<=25",  # CalVer
   "PyYAML>=5.3,<6.1",
   "schema>=0.7.5,<0.8",
   "tomli>=2.0.0,<2.1;python_version<'3.11'",