diff --git a/src/core/app/middleware/content_rewriting_middleware.py b/src/core/app/middleware/content_rewriting_middleware.py
index e7f983e8c..1229287cb 100644
--- a/src/core/app/middleware/content_rewriting_middleware.py
+++ b/src/core/app/middleware/content_rewriting_middleware.py
@@ -1,4 +1,5 @@
 import json
+from collections.abc import AsyncIterator
 from typing import Any
 
 from fastapi import Request
@@ -8,6 +9,13 @@
 
 
 class ContentRewritingMiddleware(BaseHTTPMiddleware):
+    """Middleware that performs configurable prompt/response rewriting."""
+
+    #: Maximum number of response bytes buffered when rewriting a streaming
+    #: response. Exceeding this threshold disables rewriting to prevent
+    #: unbounded memory usage that could be triggered remotely.
+    _MAX_STREAM_REWRITE_BYTES = 512_000
+
     def __init__(self, app, rewriter: ContentRewriterService):
         super().__init__(app)
         self.rewriter = rewriter
@@ -398,43 +406,72 @@ async def receive():
         response = await call_next(request_for_next_call)
 
         # Step 3: Potentially rewrite the response
-        if isinstance(response, StreamingResponse):
+        if getattr(response, "body_iterator", None) is not None:
+
+            async def stream_with_rewrite() -> AsyncIterator[bytes]:
+                buffer = bytearray()
+                rewrite_allowed = True
+                charset = getattr(response, "charset", None) or "utf-8"
 
-            async def new_iterator():
-                response_body = b""
                 async for chunk in response.body_iterator:
-                    response_body += chunk
-                rewritten_body = self.rewriter.rewrite_reply(response_body.decode())
-                yield rewritten_body.encode("utf-8")
+                    if not chunk:
+                        continue
+
+                    if isinstance(chunk, (bytes, bytearray, memoryview)):
+                        chunk_bytes = (
+                            chunk if isinstance(chunk, bytes) else bytes(chunk)
+                        )
+                    else:
+                        chunk_bytes = str(chunk).encode(charset, errors="ignore")
+
+                    if rewrite_allowed:
+                        projected_length = len(buffer) + len(chunk_bytes)
+                        if projected_length <= self._MAX_STREAM_REWRITE_BYTES:
+                            buffer.extend(chunk_bytes)
+                            continue
+
+                        rewrite_allowed = False
+                        if buffer:
+                            yield bytes(buffer)
+                            buffer.clear()
+
+                    yield bytes(chunk_bytes)
+
+                if rewrite_allowed and buffer:
+                    text = buffer.decode(charset, errors="ignore")
+                    rewritten = self.rewriter.rewrite_reply(text)
+                    yield rewritten.encode(charset)
+                elif buffer:
+                    yield bytes(buffer)
 
             background = response.background
             response.background = None
 
             return StreamingResponse(
-                new_iterator(),
+                stream_with_rewrite(),
                 status_code=response.status_code,
                 headers=dict(response.headers),
                 media_type=response.media_type,
                 background=background,
             )
-        else:
-            response_body = response.body
-            try:
-                data = json.loads(response_body)
-                is_rewritten = False
 
-                if self._rewrite_chat_response(data):
-                    is_rewritten = True
+        response_body = response.body
+        try:
+            data = json.loads(response_body)
+            is_rewritten = False
 
-                if self._rewrite_responses_output(data):
-                    is_rewritten = True
+            if self._rewrite_chat_response(data):
+                is_rewritten = True
 
-                if is_rewritten:
-                    new_body = json.dumps(data).encode("utf-8")
-                    response.body = new_body
-                    response.headers["content-length"] = str(len(new_body))
+            if self._rewrite_responses_output(data):
+                is_rewritten = True
 
-            except json.JSONDecodeError:
-                pass
+            if is_rewritten:
+                new_body = json.dumps(data).encode("utf-8")
+                response.body = new_body
+                response.headers["content-length"] = str(len(new_body))
+
+        except json.JSONDecodeError:
+            pass
 
         return response
diff --git a/tests/unit/app/middleware/test_content_rewriting_middleware.py b/tests/unit/app/middleware/test_content_rewriting_middleware.py
new file mode 100644
index 000000000..000858eb0
--- /dev/null
+++ b/tests/unit/app/middleware/test_content_rewriting_middleware.py
@@ -0,0 +1,64 @@
+from __future__ import annotations
+
+from fastapi import FastAPI
+from starlette.responses import StreamingResponse
+from starlette.testclient import TestClient
+
+from src.core.app.middleware.content_rewriting_middleware import (
+    ContentRewritingMiddleware,
+)
+
+
+class DummyRewriter:
+    """Simple stand-in for ``ContentRewriterService`` used in tests."""
+
+    def __init__(self) -> None:
+        self.rewrite_calls: list[str] = []
+
+    def rewrite_prompt(
+        self, prompt: str, prompt_type: str
+    ) -> str:  # pragma: no cover - unused
+        return prompt
+
+    def rewrite_reply(self, reply: str) -> str:
+        self.rewrite_calls.append(reply)
+        return reply.replace("foo", "bar")
+
+
+def _create_streaming_app(rewriter: DummyRewriter) -> TestClient:
+    app = FastAPI()
+
+    @app.get("/stream")
+    async def stream_endpoint() -> StreamingResponse:
+        async def generator():
+            yield b"foo"
+            yield b"foo"
+
+        return StreamingResponse(generator(), media_type="text/plain")
+
+    app.add_middleware(ContentRewritingMiddleware, rewriter=rewriter)
+    return TestClient(app)
+
+
+def test_streaming_rewrite_within_limit(monkeypatch):
+    monkeypatch.setattr(ContentRewritingMiddleware, "_MAX_STREAM_REWRITE_BYTES", 1024)
+    rewriter = DummyRewriter()
+    client = _create_streaming_app(rewriter)
+
+    response = client.get("/stream")
+
+    assert response.status_code == 200
+    assert response.text == "barbar"
+    assert rewriter.rewrite_calls == ["foofoo"]
+
+
+def test_streaming_rewrite_skips_when_limit_exceeded(monkeypatch):
+    monkeypatch.setattr(ContentRewritingMiddleware, "_MAX_STREAM_REWRITE_BYTES", 4)
+    rewriter = DummyRewriter()
+    client = _create_streaming_app(rewriter)
+
+    response = client.get("/stream")
+
+    assert response.status_code == 200
+    assert response.text == "foofoo"
+    assert rewriter.rewrite_calls == []