diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 5bd57ab9c..42f8472ea 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -31,7 +31,7 @@ jobs:
           sudo dpkg -i pandoc-2.17.1.1-1-amd64.deb
       - uses: actions/setup-python@v5
         with:
-          python-version: 3.9.16
+          python-version: 3.12.6
       - name: Cache Python dependencies
         uses: actions/cache@v4
         env:
diff --git a/.python-version b/.python-version
index 9f3d4c178..35f236d6e 100644
--- a/.python-version
+++ b/.python-version
@@ -1 +1 @@
-3.9.16
+3.12.6
diff --git a/Dockerfile b/Dockerfile
index a3c351f5e..b124c73ce 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -1,4 +1,4 @@
-FROM python:3.9-bookworm
+FROM python:3.12-bookworm
 ENV PYTHONUNBUFFERED=1
 ENV PYTHONDONTWRITEBYTECODE=1
 
diff --git a/Dockerfile.cabotage b/Dockerfile.cabotage
index d96e002a7..854e3179e 100644
--- a/Dockerfile.cabotage
+++ b/Dockerfile.cabotage
@@ -1,4 +1,4 @@
-FROM python:3.9-bullseye
+FROM python:3.12-bookworm
 COPY --from=ewdurbin/nginx-static:1.25.x /usr/bin/nginx /usr/bin/nginx
 ENV PYTHONUNBUFFERED=1
 ENV PYTHONDONTWRITEBYTECODE=1
diff --git a/base-requirements.txt b/base-requirements.txt
index a86bf74ae..d63743f4b 100644
--- a/base-requirements.txt
+++ b/base-requirements.txt
@@ -5,11 +5,11 @@ django-apptemplates==1.5
 django-admin-interface==0.24.2
 django-translation-aliases==0.1.0
 Django==4.2.16
-docutils==0.12
-Markdown==3.3.4
+docutils==0.21.2
+Markdown==3.7
 cmarkgfm==0.6.0
-Pillow==9.4.0
-psycopg2-binary==2.8.6
+Pillow==10.4.0
+psycopg2-binary==2.9.9
 python3-openid==3.2.0
 python-decouple==3.4
 # lxml used by BeautifulSoup.
diff --git a/downloads/tests/test_models.py b/downloads/tests/test_models.py
index f27e9517d..d31afae5c 100644
--- a/downloads/tests/test_models.py
+++ b/downloads/tests/test_models.py
@@ -82,8 +82,8 @@ def test_is_version_at_least(self):
 
         release_38 = Release.objects.create(name='Python 3.8.0')
         self.assertFalse(release_38.is_version_at_least_3_9)
-        self.assert_(release_38.is_version_at_least_3_5)
+        self.assertTrue(release_38.is_version_at_least_3_5)
 
         release_310 = Release.objects.create(name='Python 3.10.0')
-        self.assert_(release_310.is_version_at_least_3_9)
-        self.assert_(release_310.is_version_at_least_3_5)
+        self.assertTrue(release_310.is_version_at_least_3_9)
+        self.assertTrue(release_310.is_version_at_least_3_5)