From 29d52cd855615788dbf3dd746b6597c124c7f745 Mon Sep 17 00:00:00 2001
From: aayush598 <aayushgid598@gmail.com>
Date: Wed, 5 Aug 2026 20:50:55 +0530
Subject: [PATCH] fix(proxy): improve Headroom 404 compression error
 diagnostics

---
 .../guardrail_hooks/headroom/headroom.py      | 25 +++++++-
 .../guardrail_hooks/test_headroom.py          | 58 +++++++++++++++++++
 2 files changed, 81 insertions(+), 2 deletions(-)

diff --git a/litellm/proxy/guardrails/guardrail_hooks/headroom/headroom.py b/litellm/proxy/guardrails/guardrail_hooks/headroom/headroom.py
index 61220819d486..8bfd5cca58a6 100644
--- a/litellm/proxy/guardrails/guardrail_hooks/headroom/headroom.py
+++ b/litellm/proxy/guardrails/guardrail_hooks/headroom/headroom.py
@@ -148,6 +148,27 @@ def _restore_protected_messages(
     ]
 
 
+def _build_compress_failure_detail(status_code: int, body: str) -> dict[str, object]:
+    """Build error details for failed /v1/compress responses.
+
+    Adds troubleshooting hints for known deployment-related errors while
+    preserving the upstream status code and response body.
+    """
+    if status_code == 404:
+        return {
+            "status_code": status_code,
+            "body": body,
+            "hint": (
+                "The Headroom compression endpoint returned HTTP 404. "
+                "Verify that the configured Headroom endpoint is correct and that "
+                "the compression endpoint is available. If you are using a "
+                "self-hosted deployment, some deployments require enabling remote "
+                "compression (for example, HEADROOM_COMPRESS_ALLOW_REMOTE=1)."
+            ),
+        }
+    return {"status_code": status_code, "body": body}
+
+
 def extract_hashes_from_messages(messages: list[dict[str, object]]) -> list[str]:
     hashes: Final[list[str]] = []
     for msg in messages:
@@ -417,7 +438,7 @@ async def _call_compress(
                 self._handle_compress_failure(
                     messages,
                     "Headroom compression service returned an error",
-                    {"status_code": e.response.status_code, "body": e.response.text},
+                    _build_compress_failure_detail(e.response.status_code, e.response.text),
                 ),
                 False,
                 {},
@@ -449,7 +470,7 @@ async def _call_compress(
                 self._handle_compress_failure(
                     messages,
                     "Headroom compression service returned an error",
-                    {"status_code": response.status_code, "body": response.text},
+                    _build_compress_failure_detail(response.status_code, response.text),
                 ),
                 False,
                 {},
diff --git a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_headroom.py b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_headroom.py
index 00ab39357b49..7a2772ce78c0 100644
--- a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_headroom.py
+++ b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_headroom.py
@@ -1040,6 +1040,64 @@ async def test_apply_guardrail_http_status_error_raises():
     assert exc_info.value.status_code == 502
 
 
+@pytest.mark.asyncio
+async def test_apply_guardrail_404_error_includes_troubleshooting_hint():
+    """404 responses include a troubleshooting hint for self-hosted Headroom deployments."""
+    guardrail = _make_guardrail()
+
+    inputs = GenericGuardrailAPIInputs(
+        texts=["hello"],
+        structured_messages=ORIGINAL_MESSAGES,
+    )
+
+    with patch.object(
+        guardrail.async_handler,
+        "post",
+        new_callable=AsyncMock,
+        side_effect=_make_http_status_error(404, "Not Found"),
+    ):
+        with pytest.raises(HTTPException) as exc_info:
+            await guardrail.apply_guardrail(
+                inputs=inputs,
+                request_data={},
+                input_type="request",
+            )
+
+    assert exc_info.value.status_code == 502
+    assert exc_info.value.detail["status_code"] == 404
+    assert exc_info.value.detail["body"] == "Not Found"
+    assert "hint" in exc_info.value.detail
+    assert "HEADROOM_COMPRESS_ALLOW_REMOTE=1" in exc_info.value.detail["hint"]
+
+
+@pytest.mark.asyncio
+async def test_apply_guardrail_non_404_error_omits_troubleshooting_hint():
+    guardrail = _make_guardrail()
+
+    inputs = GenericGuardrailAPIInputs(
+        texts=["hello"],
+        structured_messages=ORIGINAL_MESSAGES,
+    )
+
+    with patch.object(
+        guardrail.async_handler,
+        "post",
+        new_callable=AsyncMock,
+        side_effect=_make_http_status_error(500, "headroom internal error"),
+    ):
+        with pytest.raises(HTTPException) as exc_info:
+            await guardrail.apply_guardrail(
+                inputs=inputs,
+                request_data={},
+                input_type="request",
+            )
+
+    assert exc_info.value.status_code == 502
+    assert exc_info.value.detail["status_code"] == 500
+    assert exc_info.value.detail["body"] == "headroom internal error"
+    assert "hint" not in exc_info.value.detail
+
+
 @pytest.mark.asyncio
 async def test_apply_guardrail_http_status_error_fail_open_forwards_uncompressed():
     guardrail = _make_guardrail(unreachable_fallback="fail_open")