diff --git a/.github/workflows/flake8.yml b/.github/workflows/flake8.yml
index 0a8c0c3..af1b394 100644
--- a/.github/workflows/flake8.yml
+++ b/.github/workflows/flake8.yml
@@ -16,7 +16,7 @@ permissions:
 jobs:
   Run:
     name: "Flake8"
-    runs-on: "ubuntu-20.04"
+    runs-on: "ubuntu-22.04"
 
     steps:
       - name: Checkout 🛎️
diff --git a/.github/workflows/mypy.yml b/.github/workflows/mypy.yml
index 10c6f30..bd74787 100644
--- a/.github/workflows/mypy.yml
+++ b/.github/workflows/mypy.yml
@@ -20,7 +20,7 @@ jobs:
 
     strategy:
       matrix:
-        os: ['ubuntu-20.04', 'windows-2019']
+        os: ['ubuntu-22.04', 'windows-2019']
       fail-fast: false
 
     steps:
diff --git a/.github/workflows/python_ci.yml b/.github/workflows/python_ci.yml
index 17b9b63..9bed236 100644
--- a/.github/workflows/python_ci.yml
+++ b/.github/workflows/python_ci.yml
@@ -28,14 +28,14 @@ jobs:
       fail-fast: False
       matrix:
         config:
-          - {python-version: "3.7", testenvs: "py37-click{7.1,8.0,8.1},build", experimental: False}
+          - {python-version: "3.7", testenvs: "py37-click{7.1,8.0,8.1}", experimental: False}
           - {python-version: "3.8", testenvs: "py38-click{7.1,8.0,8.1},build", experimental: False}
           - {python-version: "3.9", testenvs: "py39-click{7.1,8.0,8.1},build", experimental: False}
           - {python-version: "3.10", testenvs: "py310-click{7.1,8.0,8.1},build", experimental: False}
           - {python-version: "3.11", testenvs: "py311-click{7.1,8.0,8.1},build", experimental: False}
           - {python-version: "3.12", testenvs: "py312-click{7.1,8.0,8.1},build", experimental: False}
           - {python-version: "3.13", testenvs: "py313-click{7.1,8.0,8.1},build", experimental: False}
-          - {python-version: "pypy-3.7", testenvs: "pypy37-click{7.1,8.0,8.1},build", experimental: False}
+          - {python-version: "pypy-3.7", testenvs: "pypy37-click{7.1,8.0,8.1}", experimental: False}
           - {python-version: "pypy-3.8", testenvs: "pypy38-click{7.1,8.0,8.1},build", experimental: False}
           - {python-version: "pypy-3.9-v7.3.15", testenvs: "pypy39-click{7.1,8.0,8.1},build", experimental: True}
 
diff --git a/.github/workflows/python_ci_linux.yml b/.github/workflows/python_ci_linux.yml
index a58698a..6d0a1f1 100644
--- a/.github/workflows/python_ci_linux.yml
+++ b/.github/workflows/python_ci_linux.yml
@@ -19,8 +19,8 @@ permissions:
 
 jobs:
   tests:
-    name: "ubuntu-20.04 / Python ${{ matrix.config.python-version }}"
-    runs-on: "ubuntu-20.04"
+    name: "ubuntu-22.04 / Python ${{ matrix.config.python-version }}"
+    runs-on: "ubuntu-22.04"
     continue-on-error: ${{ matrix.config.experimental }}
     env:
       USING_COVERAGE: '3.7,3.8,3.9,3.10,3.11,3.12,3.13,pypy-3.7,pypy-3.8,pypy-3.9'
@@ -29,14 +29,14 @@ jobs:
       fail-fast: False
       matrix:
         config:
-          - {python-version: "3.7", testenvs: "py37-click{7.1,8.0,8.1},build", experimental: False}
+          - {python-version: "3.7", testenvs: "py37-click{7.1,8.0,8.1}", experimental: False}
           - {python-version: "3.8", testenvs: "py38-click{7.1,8.0,8.1},build", experimental: False}
           - {python-version: "3.9", testenvs: "py39-click{7.1,8.0,8.1},build", experimental: False}
           - {python-version: "3.10", testenvs: "py310-click{7.1,8.0,8.1},build", experimental: False}
           - {python-version: "3.11", testenvs: "py311-click{7.1,8.0,8.1},build", experimental: False}
           - {python-version: "3.12", testenvs: "py312-click{7.1,8.0,8.1},build", experimental: False}
           - {python-version: "3.13", testenvs: "py313-click{7.1,8.0,8.1},build", experimental: False}
-          - {python-version: "pypy-3.7", testenvs: "pypy37-click{7.1,8.0,8.1},build", experimental: False}
+          - {python-version: "pypy-3.7", testenvs: "pypy37-click{7.1,8.0,8.1}", experimental: False}
           - {python-version: "pypy-3.8", testenvs: "pypy38-click{7.1,8.0,8.1},build", experimental: False}
           - {python-version: "pypy-3.9", testenvs: "pypy39-click{7.1,8.0,8.1},build", experimental: True}
 
@@ -84,7 +84,7 @@ jobs:
 
   Coverage:
     needs: tests
-    runs-on: "ubuntu-20.04"
+    runs-on: "ubuntu-22.04"
     steps:
       - name: Checkout 🛎️
         uses: "actions/checkout@v4"
@@ -133,7 +133,7 @@ jobs:
   Deploy:
     needs: tests
 
-    runs-on: "ubuntu-20.04"
+    runs-on: "ubuntu-22.04"
     steps:
       - name: Checkout 🛎️
         uses: "actions/checkout@v4"
diff --git a/.github/workflows/python_ci_macos.yml b/.github/workflows/python_ci_macos.yml
index 4026d37..2b3c78b 100644
--- a/.github/workflows/python_ci_macos.yml
+++ b/.github/workflows/python_ci_macos.yml
@@ -18,8 +18,8 @@ permissions:
 
 jobs:
   tests:
-    name: "macos-13 / Python ${{ matrix.config.python-version }}"
-    runs-on: "macos-13"
+    name: "macos-${{ matrix.config.os-ver }} / Python ${{ matrix.config.python-version }}"
+    runs-on: "macos-${{ matrix.config.os-ver }}"
     continue-on-error: ${{ matrix.config.experimental }}
     env:
       USING_COVERAGE: '3.7,3.8,3.9,3.10,3.11,3.12,3.13,pypy-3.7,pypy-3.8,pypy-3.9'
@@ -28,16 +28,16 @@ jobs:
       fail-fast: False
       matrix:
         config:
-          - {python-version: "3.7", testenvs: "py37-click{7.1,8.0,8.1},build", experimental: False}
-          - {python-version: "3.8", testenvs: "py38-click{7.1,8.0,8.1},build", experimental: False}
-          - {python-version: "3.9", testenvs: "py39-click{7.1,8.0,8.1},build", experimental: False}
-          - {python-version: "3.10", testenvs: "py310-click{7.1,8.0,8.1},build", experimental: False}
-          - {python-version: "3.11", testenvs: "py311-click{7.1,8.0,8.1},build", experimental: False}
-          - {python-version: "3.12", testenvs: "py312-click{7.1,8.0,8.1},build", experimental: False}
-          - {python-version: "3.13", testenvs: "py313-click{7.1,8.0,8.1},build", experimental: False}
-          - {python-version: "pypy-3.7", testenvs: "pypy37-click{7.1,8.0,8.1},build", experimental: False}
-          - {python-version: "pypy-3.8", testenvs: "pypy38-click{7.1,8.0,8.1},build", experimental: False}
-          - {python-version: "pypy-3.9", testenvs: "pypy39-click{7.1,8.0,8.1},build", experimental: True}
+          - {python-version: "3.7", os-ver: "13", testenvs: "py37-click{7.1,8.0,8.1}", experimental: False}
+          - {python-version: "3.8", os-ver: "14", testenvs: "py38-click{7.1,8.0,8.1},build", experimental: False}
+          - {python-version: "3.9", os-ver: "14", testenvs: "py39-click{7.1,8.0,8.1},build", experimental: False}
+          - {python-version: "3.10", os-ver: "14", testenvs: "py310-click{7.1,8.0,8.1},build", experimental: False}
+          - {python-version: "3.11", os-ver: "14", testenvs: "py311-click{7.1,8.0,8.1},build", experimental: False}
+          - {python-version: "3.12", os-ver: "14", testenvs: "py312-click{7.1,8.0,8.1},build", experimental: False}
+          - {python-version: "3.13", os-ver: "14", testenvs: "py313-click{7.1,8.0,8.1},build", experimental: False}
+          - {python-version: "pypy-3.7", os-ver: "13", testenvs: "pypy37-click{7.1,8.0,8.1}", experimental: False}
+          - {python-version: "pypy-3.8", os-ver: "14", testenvs: "pypy38-click{7.1,8.0,8.1},build", experimental: False}
+          - {python-version: "pypy-3.9", os-ver: "14", testenvs: "pypy39-click{7.1,8.0,8.1},build", experimental: True}
 
     steps:
       - name: Checkout 🛎️
diff --git a/.readthedocs.yml b/.readthedocs.yml
index e928b70..83fc025 100644
--- a/.readthedocs.yml
+++ b/.readthedocs.yml
@@ -13,7 +13,7 @@ python:
    - requirements: requirements.txt
    - requirements: doc-source/requirements.txt
 build:
-  os: ubuntu-20.04
+  os: ubuntu-22.04
   tools:
     python: '3.9'
   jobs: