diff --git a/litellm/llms/azure_ai/passthrough/transformation.py b/litellm/llms/azure_ai/passthrough/transformation.py
index ed630bc6f2b..f2be1d95593 100644
--- a/litellm/llms/azure_ai/passthrough/transformation.py
+++ b/litellm/llms/azure_ai/passthrough/transformation.py
@@ -62,6 +62,10 @@ def foundry_root(api_base: str) -> str:
     return str(url.copy_with(path="/" + "/".join(root_segments), query=None)).rstrip("/")
 
 
+def is_repeated_native_prefix(native_segments: tuple[str, ...], overlap: int) -> bool:
+    return overlap == len(native_segments) or native_segments[0] == "openai"
+
+
 def without_repeated_native_prefix(root: str, native_endpoint: str) -> str:
     url: Final = httpx.URL(root)
     root_segments: Final = tuple(segment for segment in url.path.split("/") if segment)
@@ -71,6 +75,7 @@ def without_repeated_native_prefix(root: str, native_endpoint: str) -> str:
             length
             for length in range(min(len(root_segments), len(native_segments)), 0, -1)
             if tuple(segment.casefold() for segment in root_segments[-length:]) == native_segments[:length]
+            and is_repeated_native_prefix(native_segments, length)
         ),
         0,
     )
diff --git a/tests/test_litellm/llms/azure_ai/passthrough/test_azure_ai_passthrough_transformation.py b/tests/test_litellm/llms/azure_ai/passthrough/test_azure_ai_passthrough_transformation.py
index 1b9036c50c5..c8007acf70f 100644
--- a/tests/test_litellm/llms/azure_ai/passthrough/test_azure_ai_passthrough_transformation.py
+++ b/tests/test_litellm/llms/azure_ai/passthrough/test_azure_ai_passthrough_transformation.py
@@ -153,6 +153,20 @@ def test_deployment_root_api_base_is_not_repeated_when_the_relay_carries_the_dep
     assert base == "https://my-resource.openai.azure.com"
 
 
+def test_deployment_named_like_the_first_native_segment_keeps_its_deployment_root():
+    url, base = AzureAIPassthroughConfig().get_complete_url(
+        api_base="https://my-resource.openai.azure.com/openai/deployments/chat",
+        api_key="key",
+        model="chat",
+        endpoint="aoai-chat/chat/completions",
+        request_query_params={"api-version": "2024-10-21"},
+        litellm_params={"litellm_metadata": {"model_group": "aoai-chat"}},
+    )
+
+    assert str(url) == "https://my-resource.openai.azure.com/openai/deployments/chat/chat/completions?api-version=2024-10-21"
+    assert base == "https://my-resource.openai.azure.com/openai/deployments/chat"
+
+
 def test_parse_relay_under_a_models_api_base_targets_the_foundry_root():
     url, _ = AzureAIPassthroughConfig().get_complete_url(
         api_base=f"{FOUNDRY_BASE}/models",