diff --git a/python/mirascope/llm/providers/openai/responses/_utils/encode.py b/python/mirascope/llm/providers/openai/responses/_utils/encode.py
index d918c3ea78..00df5c2730 100644
--- a/python/mirascope/llm/providers/openai/responses/_utils/encode.py
+++ b/python/mirascope/llm/providers/openai/responses/_utils/encode.py
@@ -47,12 +47,13 @@
 
 # Thinking level to a float multiplier % of max tokens
 THINKING_LEVEL_TO_EFFORT: dict[ThinkingLevel, ReasoningEffort] = {
-    "none": "minimal",
     "default": "medium",
+    "none": "none",
     "minimal": "minimal",
     "low": "low",
     "medium": "medium",
-    "max": "high",
+    "high": "high",
+    "max": "xhigh",
 }
 
 
diff --git a/python/pyproject.toml b/python/pyproject.toml
index 2e7d3b8c60..6e5e6873d1 100644
--- a/python/pyproject.toml
+++ b/python/pyproject.toml
@@ -57,7 +57,7 @@ Changelog = "https://github.com/Mirascope/mirascope/releases"
 anthropic = ["anthropic>=0.75.0,<1.0"]
 api = ["pydantic-settings>=2.12.0"]
 google = ["google-genai>=1.48.0,<2", "pillow>=10.4.0,<11", "proto-plus>=1.24.0"]
-openai = ["openai>=2.7.1,<3"]
+openai = ["openai>=2.14.0,<3"]
 mcp = ["mcp>=1.25.0,<2"]
 ops = [
     "opentelemetry-sdk>=1.38.0,<2",
diff --git a/python/tests/ops/_internal/test_closure.py b/python/tests/ops/_internal/test_closure.py
index 6299d220ff..9717ef464a 100644
--- a/python/tests/ops/_internal/test_closure.py
+++ b/python/tests/ops/_internal/test_closure.py
@@ -485,7 +485,7 @@ def aliased_module_import_fn(query: str) -> str:
 """
     )
     assert closure.dependencies == snapshot(
-        {"openai": {"version": "2.7.1", "extras": None}}
+        {"openai": {"version": "2.14.0", "extras": None}}
     )
 
 
@@ -506,7 +506,7 @@ def aliased_import_fn(query: str) -> str:
 """
     )
     assert closure.dependencies == snapshot(
-        {"openai": {"version": "2.7.1", "extras": None}}
+        {"openai": {"version": "2.14.0", "extras": None}}
     )
 
 
@@ -640,7 +640,7 @@ def annotated_assignment_fn() -> str:
 """
     )
     assert closure.dependencies == snapshot(
-        {"openai": {"version": "2.7.1", "extras": None}}
+        {"openai": {"version": "2.14.0", "extras": None}}
     )
 
 
@@ -664,7 +664,7 @@ def internal_imports_fn() -> str:
 """
     )
     assert closure.dependencies == snapshot(
-        {"openai": {"version": "2.7.1", "extras": None}}
+        {"openai": {"version": "2.14.0", "extras": None}}
     )
 
 
diff --git a/python/uv.lock b/python/uv.lock
index 4f9600b287..2ef602c617 100644
--- a/python/uv.lock
+++ b/python/uv.lock
@@ -1263,7 +1263,7 @@ requires-dist = [
     { name = "mcp", marker = "extra == 'mcp'", specifier = ">=1.25.0,<2" },
     { name = "mirascope", extras = ["anthropic", "api", "google", "openai", "mcp", "ops", "mlx"], marker = "extra == 'all'" },
     { name = "mlx-lm", marker = "extra == 'mlx'", specifier = ">=0.28.4,<1" },
-    { name = "openai", marker = "extra == 'openai'", specifier = ">=2.7.1,<3" },
+    { name = "openai", marker = "extra == 'openai'", specifier = ">=2.14.0,<3" },
     { name = "opentelemetry-api", marker = "extra == 'ops'", specifier = ">=1.38.0,<2" },
     { name = "opentelemetry-exporter-otlp", marker = "extra == 'ops'", specifier = ">=1.38.0,<2" },
     { name = "opentelemetry-instrumentation", marker = "extra == 'ops'", specifier = ">=0.59b0,<1" },
@@ -1640,7 +1640,7 @@ wheels = [
 
 [[package]]
 name = "openai"
-version = "2.7.1"
+version = "2.14.0"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "anyio" },
@@ -1652,9 +1652,9 @@ dependencies = [
     { name = "tqdm" },
     { name = "typing-extensions" },
 ]
-sdist = { url = "https://files.pythonhosted.org/packages/51/a2/f4023c1e0c868a6a5854955b3374f17153388aed95e835af114a17eac95b/openai-2.7.1.tar.gz", hash = "sha256:df4d4a3622b2df3475ead8eb0fbb3c27fd1c070fa2e55d778ca4f40e0186c726", size = 595933, upload-time = "2025-11-04T06:07:23.069Z" }
+sdist = { url = "https://files.pythonhosted.org/packages/d8/b1/12fe1c196bea326261718eb037307c1c1fe1dedc2d2d4de777df822e6238/openai-2.14.0.tar.gz", hash = "sha256:419357bedde9402d23bf8f2ee372fca1985a73348debba94bddff06f19459952", size = 626938, upload-time = "2025-12-19T03:28:45.742Z" }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/8c/74/6bfc3adc81f6c2cea4439f2a734c40e3a420703bbcdc539890096a732bbd/openai-2.7.1-py3-none-any.whl", hash = "sha256:2f2530354d94c59c614645a4662b9dab0a5b881c5cd767a8587398feac0c9021", size = 1008780, upload-time = "2025-11-04T06:07:20.818Z" },
+    { url = "https://files.pythonhosted.org/packages/27/4b/7c1a00c2c3fbd004253937f7520f692a9650767aa73894d7a34f0d65d3f4/openai-2.14.0-py3-none-any.whl", hash = "sha256:7ea40aca4ffc4c4a776e77679021b47eec1160e341f42ae086ba949c9dcc9183", size = 1067558, upload-time = "2025-12-19T03:28:43.727Z" },
 ]
 
 [[package]]