diff --git a/google/genai/_gaos/google_genai.py b/google/genai/_gaos/google_genai.py
index 95c9fdf7c..7dfa5c666 100644
--- a/google/genai/_gaos/google_genai.py
+++ b/google/genai/_gaos/google_genai.py
@@ -1021,7 +1021,8 @@ def upload(
             or 'v1alpha'
         ).lstrip('/')
 
-        handshake_res = self._internal.start_upload(
+        handshake_res = wrap_sdk_call(
+            self._internal.start_upload,
             environment=clean_env,
             path=clean_path,
             x_goog_upload_header_content_length=size_bytes,
@@ -1179,7 +1180,8 @@ async def upload(
             or 'v1alpha'
         ).lstrip('/')
 
-        handshake_res = await self._internal.start_upload(
+        handshake_res = await async_wrap_sdk_call(
+            self._internal.start_upload,
             environment=clean_env,
             path=clean_path,
             x_goog_upload_header_content_length=size_bytes,
diff --git a/google/genai/_gaos/lib/compat_errors.py b/google/genai/_gaos/lib/compat_errors.py
index 7bd524927..c25a70db2 100644
--- a/google/genai/_gaos/lib/compat_errors.py
+++ b/google/genai/_gaos/lib/compat_errors.py
@@ -350,9 +350,9 @@ def after_error(
         response: Optional[httpx.Response],
         error: Optional[Exception],
     ) -> tuple[Optional[httpx.Response], Optional[Exception]]:
-        if error is None:
-            return response, error
-        return response, wrap_sdk_error(error)  # type: ignore[return-value]
+        # Runs once per attempt inside the retry loop, which only retries raw
+        # httpx errors, so `wrap_sdk_call` translates after the last attempt.
+        return response, error
 
     def after_parse_error(
         self,
diff --git a/google/genai/tests/interactions/test_httpx_compat.py b/google/genai/tests/interactions/test_httpx_compat.py
index ea867f6a0..f6f6fdfb7 100644
--- a/google/genai/tests/interactions/test_httpx_compat.py
+++ b/google/genai/tests/interactions/test_httpx_compat.py
@@ -113,6 +113,67 @@ async def failing_agen():
   assert "async stream network broken" in str(exc_info.value)
 
 
+def test_interactions_retries_connection_errors():
+  recorded_requests = []
+
+  def handler(request: httpx.Request) -> httpx.Response:
+    recorded_requests.append(request)
+    raise httpx.ConnectError("connection refused", request=request)
+
+  client = client_lib.Client(
+      api_key="fake-key",
+      http_options={
+          "client_args": {"transport": httpx.MockTransport(handler)},
+          "retry_options": {"attempts": 2, "initial_delay": 0, "max_delay": 0},
+      },
+  )
+  with pytest.raises(compat_errors.APIConnectionError) as exc_info:
+    client.interactions.create(model="gemini-1.5-flash", input="Hello")
+  assert len(recorded_requests) > 1
+  assert isinstance(exc_info.value.__cause__, httpx.ConnectError)
+
+
+@pytest.mark.asyncio
+async def test_async_interactions_retries_connection_errors():
+  recorded_requests = []
+
+  def handler(request: httpx.Request) -> httpx.Response:
+    recorded_requests.append(request)
+    raise httpx.ConnectError("connection refused", request=request)
+
+  client = client_lib.Client(
+      api_key="fake-key",
+      http_options={
+          "async_client_args": {"transport": httpx.MockTransport(handler)},
+          "retry_options": {"attempts": 2, "initial_delay": 0, "max_delay": 0},
+      },
+  )
+  with pytest.raises(compat_errors.APIConnectionError) as exc_info:
+    await client.aio.interactions.create(
+        model="gemini-1.5-flash", input="Hello"
+    )
+  assert len(recorded_requests) > 1
+  assert isinstance(exc_info.value.__cause__, httpx.ConnectError)
+
+
+def test_environment_file_upload_wraps_connection_errors():
+  def handler(request: httpx.Request) -> httpx.Response:
+    raise httpx.ConnectError("connection refused", request=request)
+
+  client = client_lib.Client(
+      api_key="fake-key",
+      http_options={
+          "client_args": {"transport": httpx.MockTransport(handler)},
+          "retry_options": {"attempts": 1, "initial_delay": 0, "max_delay": 0},
+      },
+  )
+  with pytest.raises(compat_errors.APIConnectionError) as exc_info:
+    client.environments.files.upload(
+        environment="env_123", path="src/main.py", file=b"print('hello')"
+    )
+  assert isinstance(exc_info.value.__cause__, httpx.ConnectError)
+
+
 # --- httpx2 tests (run in CI when httpx2 is installed) ---