diff --git a/.github/workflows/backend-checks.yml b/.github/workflows/backend-checks.yml
index f0019bf877..28d2a586b2 100644
--- a/.github/workflows/backend-checks.yml
+++ b/.github/workflows/backend-checks.yml
@@ -18,7 +18,7 @@ jobs:
       - uses: actions/checkout@v6
       - uses: actions/setup-python@v5
         with:
-          python-version: "3.13.5"
+          python-version: "3.14.7"
       - name: Install uv
         uses: astral-sh/setup-uv@08807647e7069bb48b6ef5acd8ec9567f424441b
         id: setup-uv
diff --git a/.github/workflows/backend-test.yml b/.github/workflows/backend-test.yml
index 4c4651834c..5c8fece86e 100644
--- a/.github/workflows/backend-test.yml
+++ b/.github/workflows/backend-test.yml
@@ -38,7 +38,7 @@ jobs:
       - uses: actions/checkout@v6
       - uses: actions/setup-python@v5
         with:
-          python-version: "3.13.5"
+          python-version: "3.14.7"
       - name: Install uv
         uses: astral-sh/setup-uv@08807647e7069bb48b6ef5acd8ec9567f424441b
         id: setup-uv
diff --git a/.github/workflows/claude.yml b/.github/workflows/claude.yml
index 41bb9b1e9e..65dc551360 100644
--- a/.github/workflows/claude.yml
+++ b/.github/workflows/claude.yml
@@ -70,7 +70,7 @@ jobs:
           fetch-depth: 1
       - uses: actions/setup-python@v5
         with:
-          python-version: "3.13.5"
+          python-version: "3.14.7"
       - name: Install uv
         uses: astral-sh/setup-uv@08807647e7069bb48b6ef5acd8ec9567f424441b
         id: setup-uv
diff --git a/.github/workflows/graphql-schema.yml b/.github/workflows/graphql-schema.yml
index ef4d8d6232..38c7bb1989 100644
--- a/.github/workflows/graphql-schema.yml
+++ b/.github/workflows/graphql-schema.yml
@@ -22,7 +22,7 @@ jobs:
 
       - uses: actions/setup-python@v5
         with:
-          python-version: "3.13.5"
+          python-version: "3.14.7"
 
       - name: Install uv
         uses: astral-sh/setup-uv@08807647e7069bb48b6ef5acd8ec9567f424441b
diff --git a/.tool-versions b/.tool-versions
index f6baa1bd83..0ae7835904 100644
--- a/.tool-versions
+++ b/.tool-versions
@@ -1,6 +1,6 @@
 nodejs 21.7.3
 terraform 1.3.4
-python    3.13.5
+python    3.14.7
 rust      1.61.0
 pnpm      9
 opentofu  1.9.0
diff --git a/AGENTS.md b/AGENTS.md
index 215247b6e1..46eec2935e 100644
--- a/AGENTS.md
+++ b/AGENTS.md
@@ -72,7 +72,7 @@ The project uses Docker Compose for local development with services:
 
 ## Important Notes
 
-- Python version: 3.13.5+ (specified in pyproject.toml)
+- Python version: 3.14.7+ (specified in pyproject.toml)
 - Uses `uv` for Python package management
 - Uses `pnpm` for Node.js package management
 - GraphQL schema auto-generation from Django backend to frontend
diff --git a/Dockerfile.python.local b/Dockerfile.python.local
index b2457963ac..9b022436c6 100644
--- a/Dockerfile.python.local
+++ b/Dockerfile.python.local
@@ -1,6 +1,6 @@
 ARG FUNCTION_DIR="/home/app/"
 
-FROM python:3.13.5
+FROM python:3.14.7
 
 RUN apt update -y && apt install -y ffmpeg libsm6 libxext6
 
diff --git a/backend/Dockerfile b/backend/Dockerfile
index 3af0515d2e..f6dc511d95 100644
--- a/backend/Dockerfile
+++ b/backend/Dockerfile
@@ -1,7 +1,7 @@
 # check=skip=SecretsUsedInArgOrEnv
 ARG FUNCTION_DIR="/home/app"
 
-FROM python:3.13.5-slim AS base
+FROM python:3.14.7-slim AS base
 
 ENV DJANGO_SETTINGS_MODULE=pycon.settings.prod \
     AWS_MEDIA_BUCKET=example \
diff --git a/backend/api/grants/mutations.py b/backend/api/grants/mutations.py
index d067e49e40..322c3be0de 100644
--- a/backend/api/grants/mutations.py
+++ b/backend/api/grants/mutations.py
@@ -89,7 +89,7 @@ def set_answers_errors(self, answer_errors: dict):
         # add_error() appends to list fields, so the JSON map is set directly
         self._has_errors = True
         if not self.errors:
-            self.errors = self.__annotations__["errors"]()
+            self.errors = type(self).__annotations__["errors"]()
         self.errors.answers_errors = answer_errors
 
 
diff --git a/backend/api/types.py b/backend/api/types.py
index e6a8136e7f..db074814ac 100644
--- a/backend/api/types.py
+++ b/backend/api/types.py
@@ -34,7 +34,7 @@ def add_error(self, field: str, message: str):
         self._has_errors = True
 
         if not self.errors:
-            self.errors = self.__annotations__["errors"]()
+            self.errors = type(self).__annotations__["errors"]()
 
         field = self.build_field_name(field)
         parts = field.split(".")
diff --git a/backend/pyproject.toml b/backend/pyproject.toml
index ac62ca2875..35b1b1ec92 100644
--- a/backend/pyproject.toml
+++ b/backend/pyproject.toml
@@ -41,10 +41,10 @@ known-first-party = [
 
 
 [project]
-requires-python = ">=3.13.5"
+requires-python = ">=3.14.7"
 dependencies = [
     "django==5.2.8",
-    "django-environ==0.10.0",
+    "django-environ==0.14.0",
     "django-model-utils==5.0.0",
     "django-timezone-field==7.0",
     "certifi==2024.7.4",
@@ -73,7 +73,7 @@ dependencies = [
     "django-import-export<4.0.0,>=3.2.0",
     "dal-admin-filters==1.1.0",
     "django-markdownify==0.9.5",
-    "django-imagekit==5.0.0",
+    "django-imagekit==6.0.0",
     "pillow==12.2.0",
     "redis[hiredis]==8.1.0",
     "google-api-python-client<3.0.0,>=2.94.0",
@@ -97,7 +97,7 @@ dependencies = [
     "cryptography>=48.0.1",
     "openai>=1.52.0",
     "pydantic>=2.13.3",
-    "gunicorn>=23.0.0",
+    "gunicorn==26.2.0",
     "tinycss2>=1.4.0",
     "pypdf>=6.13.3",
     "ipython>=8.30.0",
diff --git a/backend/uv.lock b/backend/uv.lock
index d7787627f9..d737827b04 100644
--- a/backend/uv.lock
+++ b/backend/uv.lock
@@ -1,19 +1,15 @@
 version = 1
 revision = 3
-requires-python = ">=3.13.5"
+requires-python = ">=3.14.7"
 resolution-markers = [
     "python_full_version >= '3.15' and sys_platform == 'win32'",
     "python_full_version >= '3.15' and sys_platform == 'emscripten'",
     "python_full_version >= '3.15' and sys_platform != 'darwin' and sys_platform != 'emscripten' and sys_platform != 'win32'",
-    "python_full_version == '3.14.*' and sys_platform == 'win32'",
-    "python_full_version == '3.14.*' and sys_platform == 'emscripten'",
-    "python_full_version == '3.14.*' and sys_platform != 'darwin' and sys_platform != 'emscripten' and sys_platform != 'win32'",
     "python_full_version >= '3.15' and sys_platform == 'darwin'",
-    "python_full_version == '3.14.*' and sys_platform == 'darwin'",
-    "python_full_version < '3.14' and sys_platform == 'win32'",
-    "python_full_version < '3.14' and sys_platform == 'emscripten'",
-    "python_full_version < '3.14' and sys_platform != 'darwin' and sys_platform != 'emscripten' and sys_platform != 'win32'",
-    "python_full_version < '3.14' and sys_platform == 'darwin'",
+    "python_full_version < '3.15' and sys_platform == 'win32'",
+    "python_full_version < '3.15' and sys_platform == 'emscripten'",
+    "python_full_version < '3.15' and sys_platform != 'darwin' and sys_platform != 'emscripten' and sys_platform != 'win32'",
+    "python_full_version < '3.15' and sys_platform == 'darwin'",
 ]
 
 [[package]]
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-    { url = "https://files.pythonhosted.org/packages/bb/5f/f652055e18d2627e2eed94c7f31a792127cfe38df786635395d742321674/argon2_cffi_bindings-26.1.0-cp313-cp313-pyemscripten_2025_0_wasm32.whl", hash = "sha256:af11ac37a7c53dc16cb7950a6190851b0870fe218b6c60c0bb7ac355234e3083", size = 15434, upload-time = "2026-08-20T07:32:53.143Z" },
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     { url = "https://files.pythonhosted.org/packages/91/0a/c25af768f6b75a5a71e31207f87c540656b2808c015260444a22763221ad/argon2_cffi_bindings-26.1.0-cp314-cp314t-macosx_11_0_arm64.whl", hash = "sha256:28524438cd3e723f25412f63d4fd516ff5bae9ae5aa56acbe2a1404398a0cf31", size = 25683, upload-time = "2026-08-20T07:32:55.05Z" },
     { url = "https://files.pythonhosted.org/packages/a8/7e/be212c751ab0bcea7f646615f933bf262e8e50b3f7bef32f861d0a2d066b/argon2_cffi_bindings-26.1.0-cp314-cp314t-manylinux_2_26_aarch64.manylinux_2_28_aarch64.whl", hash = "sha256:ac82fc756a446b6ccd7139ce70efa9d8bbe541e7ad579a12dcb52764b7175c5f", size = 27311, upload-time = "2026-08-20T07:32:56.166Z" },
@@ -258,8 +253,8 @@ requires-dist = [
     { name = "dal-admin-filters", specifier = "==1.1.0" },
     { name = "django", specifier = "==5.2.8" },
     { name = "django-autocomplete-light", specifier = "==3.9.4" },
-    { name = "django-environ", specifier = "==0.10.0" },
-    { name = "django-imagekit", specifier = "==5.0.0" },
+    { name = "django-environ", specifier = "==0.14.0" },
+    { name = "django-imagekit", specifier = "==6.0.0" },
     { name = "django-import-export", specifier = ">=3.2.0,<4.0.0" },
     { name = "django-markdownify", specifier = "==0.9.5" },
     { name = "django-model-utils", specifier = "==5.0.0" },
@@ -272,7 +267,7 @@ requires-dist = [
     { name = "google-api-python-client", specifier = ">=2.94.0,<3.0.0" },
     { name = "google-auth", specifier = ">=2.22.0,<3.0.0" },
     { name = "google-auth-oauthlib", specifier = ">=1.2.1" },
-    { name = "gunicorn", specifier = ">=23.0.0" },
+    { name = "gunicorn", specifier = "==26.2.0" },
     { name = "hashids", specifier = ">=1.2.0,<2.0.0" },
     { name = "icalendar", specifier = ">=5.0.11" },
     { name = "idna", specifier = "==3.15" },
@@ -427,16 +422,6 @@ version = "1.2.0"
 source = { registry = "https://pypi.org/simple" }
 sdist = { url = "https://files.pythonhosted.org/packages/f7/16/c92ca344d646e71a43b8bb353f0a6490d7f6e06210f8554c8f874e454285/brotli-1.2.0.tar.gz", hash = "sha256:e310f77e41941c13340a95976fe66a8a95b01e783d430eeaf7a2f87e0a57dd0a", size = 7388632, upload-time = "2025-11-05T18:39:42.86Z" }
 wheels = [
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diff --git a/infrastructure/applications/pycon_backend/web_task.tf b/infrastructure/applications/pycon_backend/web_task.tf
index 62df88c44f..6184fc5a19 100644
--- a/infrastructure/applications/pycon_backend/web_task.tf
+++ b/infrastructure/applications/pycon_backend/web_task.tf
@@ -9,7 +9,7 @@ resource "aws_ecs_task_definition" "web" {
       essential         = true
 
       command = [
-        "gunicorn", "-w", "5", "-b", "0.0.0.0:8000", "pycon.wsgi"
+        "gunicorn", "--preload", "-w", "5", "-b", "0.0.0.0:8000", "pycon.wsgi"
       ]
 
       dockerLabels = {