diff --git a/starlette/responses.py b/starlette/responses.py
index bbd205b13a..dae0a9dd17 100644
--- a/starlette/responses.py
+++ b/starlette/responses.py
@@ -253,7 +253,7 @@ async def stream_response(self, send: Send) -> None:
                 # We got an ASGI message which is not response body (eg: pathsend)
                 should_close_body = False
                 await send(chunk)
-                break
+                continue
             if isinstance(chunk, str):
                 chunk = chunk.encode(self.charset)
             await send({"type": "http.response.body", "body": chunk, "more_body": True})
diff --git a/tests/middleware/test_base.py b/tests/middleware/test_base.py
index 2176404d82..34fc27c79d 100644
--- a/tests/middleware/test_base.py
+++ b/tests/middleware/test_base.py
@@ -2,6 +2,7 @@
 
 import contextvars
 from contextlib import AsyncExitStack
+from pathlib import Path
 from typing import (
     Any,
     AsyncGenerator,
@@ -18,7 +19,12 @@
 from starlette.middleware import Middleware, _MiddlewareClass
 from starlette.middleware.base import BaseHTTPMiddleware, RequestResponseEndpoint
 from starlette.requests import Request
-from starlette.responses import PlainTextResponse, Response, StreamingResponse
+from starlette.responses import (
+    FileResponse,
+    PlainTextResponse,
+    Response,
+    StreamingResponse,
+)
 from starlette.routing import Route, WebSocketRoute
 from starlette.testclient import TestClient
 from starlette.types import ASGIApp, Message, Receive, Scope, Send
@@ -1035,3 +1041,54 @@ async def endpoint(request: Request) -> Response:
     resp.raise_for_status()
 
     assert bodies == [b"Hello, World!-foo"]
+
+
+@pytest.mark.anyio
+async def test_asgi_pathsend_events(tmpdir: Path) -> None:
+    path = tmpdir / "example.txt"
+    with path.open("w") as file:
+        file.write("<file content>")
+
+    request_body_sent = False
+    response_complete = anyio.Event()
+    events: list[Message] = []
+
+    async def endpoint_with_pathsend(_: Request) -> FileResponse:
+        return FileResponse(path)
+
+    async def passthrough(
+        request: Request, call_next: RequestResponseEndpoint
+    ) -> Response:
+        return await call_next(request)
+
+    app = Starlette(
+        middleware=[Middleware(BaseHTTPMiddleware, dispatch=passthrough)],
+        routes=[Route("/", endpoint_with_pathsend)],
+    )
+
+    scope = {
+        "type": "http",
+        "version": "3",
+        "method": "GET",
+        "path": "/",
+        "extensions": {"http.response.pathsend": {}},
+    }
+
+    async def receive() -> Message:
+        nonlocal request_body_sent
+        if not request_body_sent:
+            request_body_sent = True
+            return {"type": "http.request", "body": b"", "more_body": False}
+        await response_complete.wait()
+        return {"type": "http.disconnect"}
+
+    async def send(message: Message) -> None:
+        events.append(message)
+        if message["type"] == "http.response.pathsend":
+            response_complete.set()
+
+    await app(scope, receive, send)
+
+    assert len(events) == 2
+    assert events[0]["type"] == "http.response.start"
+    assert events[1]["type"] == "http.response.pathsend"
diff --git a/tests/middleware/test_gzip.py b/tests/middleware/test_gzip.py
index 5bfecadb72..83c9f19f3e 100644
--- a/tests/middleware/test_gzip.py
+++ b/tests/middleware/test_gzip.py
@@ -1,13 +1,24 @@
+from __future__ import annotations
+
+from pathlib import Path
 from typing import Callable
 
+import anyio
+import pytest
+
 from starlette.applications import Starlette
 from starlette.middleware import Middleware
 from starlette.middleware.gzip import GZipMiddleware
 from starlette.requests import Request
-from starlette.responses import ContentStream, PlainTextResponse, StreamingResponse
+from starlette.responses import (
+    ContentStream,
+    FileResponse,
+    PlainTextResponse,
+    StreamingResponse,
+)
 from starlette.routing import Route
 from starlette.testclient import TestClient
-from starlette.types import ASGIApp
+from starlette.types import ASGIApp, Message
 
 TestClientFactory = Callable[[ASGIApp], TestClient]
 
@@ -111,3 +122,50 @@ async def generator(bytes: bytes, count: int) -> ContentStream:
     assert response.text == "x" * 4000
     assert response.headers["Content-Encoding"] == "text"
     assert "Content-Length" not in response.headers
+
+
+@pytest.mark.anyio
+async def test_gzip_ignored_for_pathsend_responses(tmpdir: Path) -> None:
+    path = tmpdir / "example.txt"
+    with path.open("w") as file:
+        file.write("<file content>")
+
+    request_body_sent = False
+    response_complete = anyio.Event()
+    events: list[Message] = []
+
+    async def endpoint_with_pathsend(_: Request) -> FileResponse:
+        return FileResponse(path)
+
+    app = Starlette(
+        routes=[Route("/", endpoint=endpoint_with_pathsend)],
+        middleware=[Middleware(GZipMiddleware)],
+    )
+
+    scope = {
+        "type": "http",
+        "version": "3",
+        "method": "GET",
+        "path": "/",
+        "headers": [(b"accept-encoding", b"gzip, text")],
+        "extensions": {"http.response.pathsend": {}},
+    }
+
+    async def receive() -> Message:
+        nonlocal request_body_sent
+        if not request_body_sent:
+            request_body_sent = True
+            return {"type": "http.request", "body": b"", "more_body": False}
+        await response_complete.wait()
+        return {"type": "http.disconnect"}
+
+    async def send(message: Message) -> None:
+        events.append(message)
+        if message["type"] == "http.response.pathsend":
+            response_complete.set()
+
+    await app(scope, receive, send)
+
+    assert len(events) == 2
+    assert events[0]["type"] == "http.response.start"
+    assert events[1]["type"] == "http.response.pathsend"