fix(openai): match longest model prefix for context window size

lib/crewai/src/crewai/llms/providers/openai/completion.py

@@ -2445,7 +2445,11 @@ def get_context_window_size(self) -> int:
             "o4-mini": 200000,
         }
 
-        for model_prefix, size in context_windows.items():
+        # Match the most specific (longest) prefix first so that, e.g.,
+        # "gpt-4o" is not shadowed by the shorter "gpt-4" entry.
+        for model_prefix, size in sorted(
+            context_windows.items(), key=lambda x: len(x[0]), reverse=True
+        ):
             if self.model.startswith(model_prefix):
                 return int(size * CONTEXT_WINDOW_USAGE_RATIO)
 

lib/crewai/tests/llms/openai/test_openai.py

@@ -35,6 +35,32 @@ def test_openai_completion_is_used_when_no_provider_prefix():
     assert llm.model == "gpt-4o"
 
 
+def test_openai_context_window_uses_longest_prefix_match():
+    """Model prefixes must resolve to the most specific match.
+
+    Regression test: ``gpt-4o`` (and other ``gpt-4*`` models) must not be
+    shadowed by the shorter ``gpt-4`` prefix, which would collapse their
+    context window to 8192. This mirrors the Azure provider, which already
+    matches the longest prefix first.
+    """
+    from crewai.llm import CONTEXT_WINDOW_USAGE_RATIO
+
+    with patch.dict(os.environ, {"OPENAI_API_KEY": "test-key"}, clear=False):
+        llm_gpt4 = LLM(model="gpt-4")
+        llm_gpt4o = LLM(model="gpt-4o")
+        llm_gpt4o_mini = LLM(model="gpt-4o-mini")
+
+    assert isinstance(llm_gpt4o, OpenAICompletion)
+    assert llm_gpt4.get_context_window_size() == int(8192 * CONTEXT_WINDOW_USAGE_RATIO)
+    assert llm_gpt4o.get_context_window_size() == int(
+        128000 * CONTEXT_WINDOW_USAGE_RATIO
+    )
+    assert llm_gpt4o_mini.get_context_window_size() == int(
+        200000 * CONTEXT_WINDOW_USAGE_RATIO
+    )
+    assert llm_gpt4o.get_context_window_size() > llm_gpt4.get_context_window_size()
+
+
 def test_custom_openai_flag_uses_native_openai_without_provider_prefix():
     """Custom OpenAI-compatible endpoints can serve arbitrary model ids."""
     with patch.dict(os.environ, {"OPENAI_API_KEY": "test-key"}, clear=False):