diff --git a/Dockerfile b/Dockerfile
index 3d76552c0e56..57373b565ae1 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -2,7 +2,7 @@
 # Read the docs/topics/development/docker.md file for more information about this Dockerfile.
 ####################################################################################################
 
-FROM python:3.10-slim-buster as base
+FROM python:3.10-slim-bookworm as base
 
 # Should change it to use ARG instead of ENV for OLYMPIA_UID/OLYMPIA_GID
 # once the jenkins server is upgraded to support docker >= v1.9.0
@@ -43,6 +43,7 @@ RUN touch /addons-server-docker-container \
         # Git, because we're using git-checkout dependencies
         git \
         # Dependencies for mysql-python (from mysql apt repo, not debian)
+        pkg-config \
         mysql-client \
         libmysqlclient-dev \
         swig \
diff --git a/docker/mysql.list b/docker/mysql.list
index fad8e9518746..0fafbfd8a1a3 100644
--- a/docker/mysql.list
+++ b/docker/mysql.list
@@ -1 +1 @@
-deb http://repo.mysql.com/apt/debian/ buster mysql-8.0
+deb http://repo.mysql.com/apt/debian/ bookworm mysql-8.0
diff --git a/src/olympia/core/apps.py b/src/olympia/core/apps.py
index ddf34506f549..e0e675d7b028 100644
--- a/src/olympia/core/apps.py
+++ b/src/olympia/core/apps.py
@@ -1,14 +1,37 @@
 import logging
+import subprocess
 import warnings
 
 from django.apps import AppConfig
 from django.conf import settings
+from django.core.checks import Error, Tags, register
 from django.utils.translation import gettext_lazy as _
 
 
 log = logging.getLogger('z.startup')
 
 
+class CustomTags(Tags):
+    custom_setup = 'setup'
+
+
+@register(CustomTags.custom_setup)
+def uwsgi_check(app_configs, **kwargs):
+    """Custom check triggered when ./manage.py check is ran (should be done
+    as part of verifying the docker image in CI)."""
+    errors = []
+    command = ['uwsgi', '--version']
+    result = subprocess.run(command, capture_output=True)
+    if result.returncode != 0:
+        errors.append(
+            Error(
+                f'{" ".join(command)} returned a non-zero value',
+                id='setup.E001',
+            )
+        )
+    return errors
+
+
 class CoreConfig(AppConfig):
     name = 'olympia.core'
     verbose_name = _('Core')
diff --git a/src/olympia/core/tests/test_apps.py b/src/olympia/core/tests/test_apps.py
new file mode 100644
index 000000000000..7fefd167d20d
--- /dev/null
+++ b/src/olympia/core/tests/test_apps.py
@@ -0,0 +1,17 @@
+from unittest import mock
+
+from django.core.management import call_command
+from django.core.management.base import SystemCheckError
+from django.test import SimpleTestCase
+
+
+class SystemCheckIntegrationTest(SimpleTestCase):
+    def test_uwsgi_check(self):
+        call_command('check')
+
+        with mock.patch('olympia.core.apps.subprocess') as subprocess:
+            subprocess.run.return_value.returncode = 127
+            with self.assertRaisesMessage(
+                SystemCheckError, 'uwsgi --version returned a non-zero value'
+            ):
+                call_command('check')