diff --git a/.github/workflows/build.yml b/.github/workflows/build.yml
index 95702c1..6a8673e 100644
--- a/.github/workflows/build.yml
+++ b/.github/workflows/build.yml
@@ -22,7 +22,7 @@ jobs:
     strategy:
       matrix:
         os: [ubuntu-latest, macos-latest, windows-latest]
-        python: ['3.9', '3.10', '3.11', '3.12', '3.13']
+        python: ['3.11', '3.12', '3.13', '3.14']
       fail-fast: false
     runs-on: ${{ matrix.os }}
     steps:
diff --git a/.github/workflows/master_bootstrap-flask-example.yml b/.github/workflows/master_bootstrap-flask-example.yml
index 7304e28..04a9800 100644
--- a/.github/workflows/master_bootstrap-flask-example.yml
+++ b/.github/workflows/master_bootstrap-flask-example.yml
@@ -1,65 +1,65 @@
-# Docs for the Azure Web Apps Deploy action: https://github.com/Azure/webapps-deploy
-# More GitHub Actions for Azure: https://github.com/Azure/actions
-# More info on Python, GitHub Actions, and Azure App Service: https://aka.ms/python-webapps-actions
-
-name: Build and deploy Python app to Azure Web App - bootstrap-flask-example
-
-on:
-  push:
-    branches:
-      - main
-  workflow_dispatch:
-
-jobs:
-  build:
-    runs-on: ubuntu-latest
-
-    steps:
-      - uses: actions/checkout@v2
-
-      - name: Set up Python version
-        uses: actions/setup-python@v1
-        with:
-          python-version: '3.11'
-
-      - name: Create and start virtual environment
-        run: |
-          python -m venv venv
-          source venv/bin/activate
-      
-      - name: Install dependencies
-        run: |
-          pip install -r examples/requirements.txt
-          cp examples/requirements.txt examples/bootstrap5/requirements.txt
-        
-      # Optional: Add step to run tests here (PyTest, Django test suites, etc.)
-      
-      - name: Upload artifact for deployment jobs
-        uses: actions/upload-artifact@v4.4.0
-        with:
-          name: python-app
-          path: |
-            ./examples/bootstrap5/
-            !venv/
-
-  deploy:
-    runs-on: ubuntu-latest
-    needs: build
-    environment:
-      name: 'Production'
-      url: ${{ steps.deploy-to-webapp.outputs.webapp-url }}
-
-    steps:
-      - name: Download artifact from build job
-        uses: actions/download-artifact@v4.1.7
-        with:
-          name: python-app
-          path: .
-          
-      - name: 'Deploy to Azure Web App'
-        uses: azure/webapps-deploy@v2
-        id: deploy-to-webapp
-        with:
-          app-name: 'bootstrap-flask-example'
-          slot-name: 'Production'
-          publish-profile: ${{ secrets.AZUREAPPSERVICE_PUBLISHPROFILE_EA24F62410C243EEA4968476E7017059 }}
+# Docs for the Azure Web Apps Deploy action: https://github.com/Azure/webapps-deploy
+# More GitHub Actions for Azure: https://github.com/Azure/actions
+# More info on Python, GitHub Actions, and Azure App Service: https://aka.ms/python-webapps-actions
+
+name: Build and deploy Python app to Azure Web App - bootstrap-flask-example
+
+on:
+  push:
+    branches:
+      - main
+  workflow_dispatch:
+
+jobs:
+  build:
+    runs-on: ubuntu-latest
+
+    steps:
+      - uses: actions/checkout@v2
+
+      - name: Set up Python version
+        uses: actions/setup-python@v1
+        with:
+          python-version: '3.14'
+
+      - name: Create and start virtual environment
+        run: |
+          python -m venv venv
+          source venv/bin/activate
+
+      - name: Install dependencies
+        run: |
+          pip install -r examples/requirements.txt
+          cp examples/requirements.txt examples/bootstrap5/requirements.txt
+
+      # Optional: Add step to run tests here (PyTest, Django test suites, etc.)
+
+      - name: Upload artifact for deployment jobs
+        uses: actions/upload-artifact@v4.4.0
+        with:
+          name: python-app
+          path: |
+            ./examples/bootstrap5/
+            !venv/
+
+  deploy:
+    runs-on: ubuntu-latest
+    needs: build
+    environment:
+      name: 'Production'
+      url: ${{ steps.deploy-to-webapp.outputs.webapp-url }}
+
+    steps:
+      - name: Download artifact from build job
+        uses: actions/download-artifact@v4.1.7
+        with:
+          name: python-app
+          path: .
+
+      - name: 'Deploy to Azure Web App'
+        uses: azure/webapps-deploy@v2
+        id: deploy-to-webapp
+        with:
+          app-name: 'bootstrap-flask-example'
+          slot-name: 'Production'
+          publish-profile: ${{ secrets.AZUREAPPSERVICE_PUBLISHPROFILE_EA24F62410C243EEA4968476E7017059 }}
diff --git a/.github/workflows/release.yml b/.github/workflows/release.yml
index 1375607..926cab8 100644
--- a/.github/workflows/release.yml
+++ b/.github/workflows/release.yml
@@ -12,7 +12,7 @@ jobs:
       - uses: actions/checkout@v4
       - uses: actions/setup-python@v5
         with:
-          python-version: '3.12'
+          python-version: '3.14'
           cache: pip
           cache-dependency-path: requirements*/*.txt
       - run: pip install setuptools wheel build
diff --git a/CHANGES.rst b/CHANGES.rst
index b1ff3f4..fff67ee 100644
--- a/CHANGES.rst
+++ b/CHANGES.rst
@@ -1,6 +1,8 @@
 Changelog
 =========
 
+- Drop Python 3.9 and 3.10 support.
+- Upgrade dependencies.
 - Upgrade license format in pyproject.toml.
 - Upgrade to Bootstrap 5.3.6
 
diff --git a/pyproject.toml b/pyproject.toml
index b7090eb..327ef2b 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -12,11 +12,10 @@ classifiers = [
     'Operating System :: OS Independent',
     'Programming Language :: Python',
     'Programming Language :: Python :: 3',
-    'Programming Language :: Python :: 3.9',
-    'Programming Language :: Python :: 3.10',
     'Programming Language :: Python :: 3.11',
     'Programming Language :: Python :: 3.12',
     'Programming Language :: Python :: 3.13',
+    'Programming Language :: Python :: 3.14',
     'Framework :: Flask',
     'Topic :: Internet :: WWW/HTTP :: Dynamic Content',
     'Topic :: Software Development :: Libraries :: Python Modules',
diff --git a/requirements/build.txt b/requirements/build.txt
index 32a2262..f5018b4 100644
--- a/requirements/build.txt
+++ b/requirements/build.txt
@@ -15,7 +15,7 @@ pyproject-hooks==1.2.0
     # via build
 tomli==2.2.1
     # via build
-wheel==0.45.1
+wheel==0.46.2
     # via -r requirements/build.in
 zipp==3.20.2
     # via importlib-metadata
diff --git a/requirements/dev.txt b/requirements/dev.txt
index 0c0bd8c..8fc4bfb 100644
--- a/requirements/dev.txt
+++ b/requirements/dev.txt
@@ -18,7 +18,7 @@ colorama==0.4.6
     # via tox
 distlib==0.3.9
     # via virtualenv
-filelock==3.16.1
+filelock==3.20.3
     # via
     #   tox
     #   virtualenv
@@ -40,9 +40,9 @@ toposort==1.10
     # via pip-compile-multi
 tox==4.24.2
     # via -r requirements/dev.in
-virtualenv==20.29.3
+virtualenv==20.36.1
     # via tox
-wheel==0.45.1
+wheel==0.46.2
     # via pip-tools
 
 # The following packages are considered to be unsafe in a requirements file:
diff --git a/requirements/docs.txt b/requirements/docs.txt
index 2a7bec8..8409638 100644
--- a/requirements/docs.txt
+++ b/requirements/docs.txt
@@ -35,7 +35,7 @@ pygments==2.19.1
     # via sphinx
 pytz==2025.1
     # via babel
-requests==2.32.3
+requests==2.32.4
     # via sphinx
 snowballstemmer==2.2.0
     # via sphinx
@@ -61,7 +61,7 @@ sphinxcontrib-qthelp==1.0.3
     # via sphinx
 sphinxcontrib-serializinghtml==1.1.5
     # via sphinx
-urllib3==2.2.3
+urllib3==2.6.3
     # via requests
 zipp==3.20.2
     # via importlib-metadata
diff --git a/requirements/tests.txt b/requirements/tests.txt
index b863001..0a3d512 100644
--- a/requirements/tests.txt
+++ b/requirements/tests.txt
@@ -7,7 +7,7 @@
 #
 beautifulsoup4==4.13.4
     # via -r requirements/tests.in
-blinker==1.8.2
+blinker==1.9.0
     # via flask
 click==8.1.8
     # via flask
@@ -15,7 +15,7 @@ coverage[toml]==7.6.1
     # via pytest-cov
 exceptiongroup==1.2.2
     # via pytest
-flask==3.0.3
+flask==3.1.3
     # via
     #   flask-sqlalchemy
     #   flask-wtf
@@ -23,7 +23,7 @@ flask-sqlalchemy==3.1.1
     # via -r requirements/tests.in
 flask-wtf==1.2.1
     # via -r requirements/tests.in
-greenlet==3.1.1
+greenlet==3.5.5
     # via sqlalchemy
 importlib-metadata==8.5.0
     # via flask
@@ -62,7 +62,7 @@ typing-extensions==4.12.2
     # via
     #   beautifulsoup4
     #   sqlalchemy
-werkzeug==3.0.6
+werkzeug==3.1.5
     # via flask
 wtforms==3.1.2
     # via flask-wtf
diff --git a/tox.ini b/tox.ini
index ce1ff93..0adaa10 100644
--- a/tox.ini
+++ b/tox.ini
@@ -1,15 +1,14 @@
 [tox]
 isolated_build = True
-envlist = py39, py310, py311, py312, py313, flake8, docs
+envlist = py311, py312, py313, py314, flake8, docs
 skip_missing_interpreters = true
 
 [gh-actions]
 python =
-    3.9: py39
-    3.10: py310
     3.11: py311
     3.12: py312
     3.13: py313
+    3.14: py314
 
 [testenv]
 deps =