diff --git a/apps/api/pyproject.toml b/apps/api/pyproject.toml
index c002675a..153123bc 100644
--- a/apps/api/pyproject.toml
+++ b/apps/api/pyproject.toml
@@ -11,7 +11,7 @@ dependencies = [
     "psycopg[binary]>=3.3.4",
     "redis>=6.4.0",
     "pydantic~=2.13",
-    "pydantic-settings~=2.8",
+    "pydantic-settings~=2.14",
     "five08",
     "worker",
 ]
diff --git a/apps/discord_bot/pyproject.toml b/apps/discord_bot/pyproject.toml
index 792e6c95..652586cc 100644
--- a/apps/discord_bot/pyproject.toml
+++ b/apps/discord_bot/pyproject.toml
@@ -7,7 +7,7 @@ dependencies = [
     "aiohttp>=3.13.1",
     "discord.py~=2.6.0",
     "pydantic~=2.13",
-    "pydantic-settings~=2.8",
+    "pydantic-settings~=2.14",
     "python-docx>=1.2.0",
     "redis>=6.4.0",
     "openai>=2.0.0",
diff --git a/apps/worker/pyproject.toml b/apps/worker/pyproject.toml
index 326409f7..183bc5b4 100644
--- a/apps/worker/pyproject.toml
+++ b/apps/worker/pyproject.toml
@@ -10,7 +10,7 @@ dependencies = [
     "httpx>=0.28.1",
     "openai>=2.0.0",
     "pydantic~=2.13",
-    "pydantic-settings~=2.8",
+    "pydantic-settings~=2.14",
     "python-docx>=1.2.0",
     "redis>=6.4.0",
     "requests~=2.34",
diff --git a/packages/shared/pyproject.toml b/packages/shared/pyproject.toml
index d31e8424..594df815 100644
--- a/packages/shared/pyproject.toml
+++ b/packages/shared/pyproject.toml
@@ -8,7 +8,7 @@ dependencies = [
     "cryptography>=46.0.0",
     "curl-cffi>=0.10.0",
     "pydantic~=2.13",
-    "pydantic-settings~=2.8",
+    "pydantic-settings~=2.14",
     "pymupdf>=1.26.5",
     "python-docx>=1.2.0",
     "psycopg[binary]>=3.3.4",
diff --git a/uv.lock b/uv.lock
index ec5afaa2..61cabcae 100644
--- a/uv.lock
+++ b/uv.lock
@@ -199,7 +199,7 @@ requires-dist = [
     { name = "httpx", specifier = ">=0.28.1" },
     { name = "psycopg", extras = ["binary"], specifier = ">=3.3.4" },
     { name = "pydantic", specifier = "~=2.13" },
-    { name = "pydantic-settings", specifier = "~=2.8" },
+    { name = "pydantic-settings", specifier = "~=2.14" },
     { name = "pyjwt", extras = ["crypto"], specifier = ">=2.10.1" },
     { name = "redis", specifier = ">=6.4.0" },
     { name = "uvicorn", specifier = ">=0.35.0" },
@@ -619,7 +619,7 @@ requires-dist = [
     { name = "five08", editable = "packages/shared" },
     { name = "openai", specifier = ">=2.0.0" },
     { name = "pydantic", specifier = "~=2.13" },
-    { name = "pydantic-settings", specifier = "~=2.8" },
+    { name = "pydantic-settings", specifier = "~=2.14" },
     { name = "python-docx", specifier = ">=1.2.0" },
     { name = "redis", specifier = ">=6.4.0" },
     { name = "requests", specifier = "~=2.34" },
@@ -722,7 +722,7 @@ requires-dist = [
     { name = "langfuse", specifier = "==4.6.1" },
     { name = "psycopg", extras = ["binary"], specifier = ">=3.3.4" },
     { name = "pydantic", specifier = "~=2.13" },
-    { name = "pydantic-settings", specifier = "~=2.8" },
+    { name = "pydantic-settings", specifier = "~=2.14" },
     { name = "pymupdf", specifier = ">=1.26.5" },
     { name = "python-docx", specifier = ">=1.2.0" },
     { name = "redis", specifier = ">=6.4.0" },
@@ -1797,16 +1797,16 @@ wheels = [
 
 [[package]]
 name = "pydantic-settings"
-version = "2.11.0"
+version = "2.14.2"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "pydantic" },
     { name = "python-dotenv" },
     { name = "typing-inspection" },
 ]
-sdist = { url = "https://files.pythonhosted.org/packages/20/c5/dbbc27b814c71676593d1c3f718e6cd7d4f00652cefa24b75f7aa3efb25e/pydantic_settings-2.11.0.tar.gz", hash = "sha256:d0e87a1c7d33593beb7194adb8470fc426e95ba02af83a0f23474a04c9a08180", size = 188394, upload-time = "2025-09-24T14:19:11.764Z" }
+sdist = { url = "https://files.pythonhosted.org/packages/5c/b5/8f48e906c3e0205276e8bd8cb7512217a87b2685304d64be27cad5b3019f/pydantic_settings-2.14.2.tar.gz", hash = "sha256:c19dd64b19097f1de80184f0cc7b0272a13ae6e170cbf240a3e27e381ed14a5f", size = 237700, upload-time = "2026-06-19T13:44:56.324Z" }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/83/d6/887a1ff844e64aa823fb4905978d882a633cfe295c32eacad582b78a7d8b/pydantic_settings-2.11.0-py3-none-any.whl", hash = "sha256:fe2cea3413b9530d10f3a5875adffb17ada5c1e1bab0b2885546d7310415207c", size = 48608, upload-time = "2025-09-24T14:19:10.015Z" },
+    { url = "https://files.pythonhosted.org/packages/77/c1/6e422f34e569cf8e18df68d1939c81c099d2b61e4f7d9621c8a77560799c/pydantic_settings-2.14.2-py3-none-any.whl", hash = "sha256:a20c97b37910b6550d5ea50fbcc2d4187defe58cd57070b73863d069419c9440", size = 61715, upload-time = "2026-06-19T13:44:55.02Z" },
 ]
 
 [[package]]
@@ -2347,7 +2347,7 @@ requires-dist = [
     { name = "openai", specifier = ">=2.0.0" },
     { name = "psycopg", extras = ["binary"], specifier = ">=3.3.4" },
     { name = "pydantic", specifier = "~=2.13" },
-    { name = "pydantic-settings", specifier = "~=2.8" },
+    { name = "pydantic-settings", specifier = "~=2.14" },
     { name = "python-docx", specifier = ">=1.2.0" },
     { name = "redis", specifier = ">=6.4.0" },
     { name = "requests", specifier = "~=2.34" },