headroom/tests/test_ccr_tool_always_on.py
Abhay Singh d6d121e399
fix(ccr): re-inject headroom_retrieve when history references it on the sessionless path (#2440) (#2533)
## Description

Fixes #2440. `apply_session_sticky_ccr_tool` bypasses the
`SessionCcrTracker` when `session_id` is `None` (WS / pre-session paths)
and drives injection purely off the per-turn
`has_compressed_content_this_turn` flag:

```python
if not session_id:
    if not has_compressed_content_this_turn:
        ...  # skip: tool NOT re-declared
        return tools_out, False
    ...
```

If an earlier turn emitted a `headroom_retrieve` tool_use into history
but the current turn produced no fresh compression marker, the tool
definition is not re-declared in `tools`, while the forwarded history
still references it. The provider then rejects the whole request:

```
API Error: 400 Tool reference 'headroom_retrieve' not found in available tools.
```

Without a session the tracker can't remember the earlier turn's CCR, so
this is unique to the sessionless path.

## Fix

Add `history_references_ccr_tool(messages)` which detects an existing
`headroom_retrieve` call in the forwarded messages — both the Anthropic
assistant `tool_use` content block and the OpenAI assistant
`tool_calls[].function.name` shapes, fully null-guarded. On the
sessionless path, injection now fires when
`has_compressed_content_this_turn` **or** history already references the
tool, so the definition is re-declared and the request validates. The
decision is logged as a new `inject_history_reference` outcome. Both
handlers pass the signal computed from `optimized_messages` (the bytes
actually forwarded). Behavior with a real `session_id` (the sticky
tracker path) is unchanged.

## Type of Change

- [x] Bug fix (non-breaking change that fixes an issue)
- [ ] New feature (non-breaking change that adds functionality)
- [ ] Breaking change (fix or feature that would cause existing
functionality to change)
- [ ] Documentation update
- [ ] Performance improvement
- [ ] Code refactoring (no functional changes)

## Changes Made

- `headroom/proxy/helpers.py`: add `history_references_ccr_tool`; add a
`history_has_ccr_reference` parameter to `apply_session_sticky_ccr_tool`
and OR it into the sessionless injection decision.
- `headroom/proxy/tool_injection_logging.py`: add the
`inject_history_reference` decision literal.
- `headroom/proxy/handlers/anthropic.py`,
`headroom/proxy/handlers/openai.py`: pass
`history_references_ccr_tool(optimized_messages)` into the sticky-tool
call.
- `tests/test_ccr_tool_always_on.py`: regressions for the detector (both
provider shapes + malformed inputs) and for sessionless re-injection
when history references the tool.

## Testing

- [x] Unit tests pass (`pytest`)
- [x] Linting passes (`ruff check .`)
- [x] Type checking passes (`mypy headroom`)
- [x] New tests added for new functionality
- [ ] Manual testing performed

### Test Output

```text
$ python -m pytest tests/test_ccr_tool_always_on.py -q
14 passed

# with just the `or history_has_ccr_reference` condition reverted, the new
# sessionless re-injection test fails (tool not injected -> would 400)

$ uvx ruff@0.15.17 check headroom/proxy/helpers.py headroom/proxy/tool_injection_logging.py headroom/proxy/handlers/anthropic.py headroom/proxy/handlers/openai.py tests/test_ccr_tool_always_on.py
All checks passed!
$ uvx mypy@1.20.2 --ignore-missing-imports headroom/proxy/helpers.py headroom/proxy/tool_injection_logging.py
Success: no issues found in 2 source files
```

## Real Behavior Proof

- Environment: Windows 11, Python 3.12, project venv (`uv sync --extra
proxy`), `uvx ruff@0.15.17` / `uvx mypy@1.20.2`, pytest in the venv.
- Exact command / steps: called `history_references_ccr_tool` on
Anthropic `tool_use` and OpenAI `tool_calls` histories (plus
null/non-list shapes), and
`apply_session_sticky_ccr_tool(session_id=None,
has_compressed_content_this_turn=False,
history_has_ccr_reference=True)`; then temporarily reverted only the `or
history_has_ccr_reference` condition and re-ran the regression.
- Observed result: the detector returns `True` for both provider shapes
and `False`/no-crash for malformed input; with the fix the sessionless
call injects the tool (`was_injected=True`, tool present) even with no
fresh compression; with the condition reverted the same call returns
`was_injected=False` (the tool is dropped — exactly the 400 path). Ran
against the actual module via `tests/test_ccr_tool_always_on.py`.
- Not tested: a live sessionless multi-turn WS request reproducing the
upstream 400 end to end.

## Review Readiness

- [x] I have performed a self-review
- [x] This PR is ready for human review

## Checklist

- [x] My code follows the project's style guidelines
- [x] I have performed a self-review of my code
- [x] I have commented my code, particularly in hard-to-understand areas
- [ ] I have made corresponding changes to the documentation
- [x] My changes generate no new warnings
- [x] I have added tests that prove my fix is effective or that my
feature works
- [x] New and existing unit tests pass locally with my changes
- [ ] I have updated the CHANGELOG.md if applicable

Co-authored-by: JD Davis <jd@jds-macbook-air.tail2a279.ts.net>
2026-08-13 11:45:51 -05:00

438 lines
15 KiB
Python

"""PR-B7 — `headroom_retrieve` tool always-on once a session has done CCR.
These tests pin three properties:
1. After a session has performed CCR even once, every subsequent
request in that session injects the tool — even when the current
request has no fresh compression markers.
2. A session that has NEVER done CCR does not get the tool injected.
3. The tool definition bytes are byte-stable across turns (snapshot
test). Any future change to the tool schema must update the
snapshot deliberately.
Tests target the canonical helper
`headroom.proxy.helpers.apply_session_sticky_ccr_tool` plus the
`SessionCcrTracker` semantics. The CCRToolInjector legacy path is
covered by `tests/test_ccr_tool_injection.py`.
"""
from __future__ import annotations
import pytest
from headroom.ccr.tool_injection import (
CCR_TOOL_NAME,
CCRToolInjector,
create_ccr_tool_definition,
)
from headroom.proxy.helpers import (
SessionCcrTracker,
_reset_session_ccr_tracker_for_test,
apply_session_sticky_ccr_tool,
get_session_ccr_tracker,
history_references_ccr_tool,
serialize_tool_definition_canonical,
)
@pytest.fixture(autouse=True)
def _reset_tracker():
_reset_session_ccr_tracker_for_test()
yield
_reset_session_ccr_tracker_for_test()
def _has_ccr_tool(tools: list[dict] | None) -> bool:
if not tools:
return False
for t in tools:
n = t.get("name") or t.get("function", {}).get("name")
if n == CCR_TOOL_NAME:
return True
return False
# ─── Sticky-on behavior ────────────────────────────────────────────────
def test_tool_registered_on_every_request_after_first_ccr():
"""Once a session has done CCR, the tool stays registered every turn."""
session_id = "sess-abc-123"
# Turn 1: this turn produced compressed content → first-time inject.
tools_1, injected_1 = apply_session_sticky_ccr_tool(
provider="anthropic",
session_id=session_id,
request_id="req-1",
existing_tools=None,
has_compressed_content_this_turn=True,
)
assert injected_1 is True
assert _has_ccr_tool(tools_1)
# Turn 2: NO fresh compression this turn — but session has done CCR.
# Tool MUST still be injected (PR-B7 sticky-on).
tools_2, injected_2 = apply_session_sticky_ccr_tool(
provider="anthropic",
session_id=session_id,
request_id="req-2",
existing_tools=None,
has_compressed_content_this_turn=False,
)
assert injected_2 is True, "sticky replay must inject even with no fresh CCR"
assert _has_ccr_tool(tools_2)
# Turn 3: still no fresh compression — sticky-on still fires.
tools_3, injected_3 = apply_session_sticky_ccr_tool(
provider="anthropic",
session_id=session_id,
request_id="req-3",
existing_tools=None,
has_compressed_content_this_turn=False,
)
assert injected_3 is True
assert _has_ccr_tool(tools_3)
def test_tool_not_registered_if_session_never_did_ccr():
"""A session that never produced CCR markers gets no tool injection."""
session_id = "fresh-session-no-ccr"
tools, injected = apply_session_sticky_ccr_tool(
provider="anthropic",
session_id=session_id,
request_id="req-1",
existing_tools=None,
has_compressed_content_this_turn=False,
)
assert injected is False
assert not _has_ccr_tool(tools)
# Tracker must NOT have recorded this session.
assert get_session_ccr_tracker().has_done_ccr("anthropic", session_id) is False
# Do it again — same outcome, no state leakage.
tools, injected = apply_session_sticky_ccr_tool(
provider="anthropic",
session_id=session_id,
request_id="req-2",
existing_tools=None,
has_compressed_content_this_turn=False,
)
assert injected is False
assert not _has_ccr_tool(tools)
def test_independent_sessions_track_independently():
"""Two distinct session_ids do not bleed sticky state."""
sess_a = "sess-A"
sess_b = "sess-B"
# A does CCR; B does not.
apply_session_sticky_ccr_tool(
provider="anthropic",
session_id=sess_a,
request_id="r1",
existing_tools=None,
has_compressed_content_this_turn=True,
)
# B's next turn (no fresh CCR) must NOT auto-inject.
tools_b, injected_b = apply_session_sticky_ccr_tool(
provider="anthropic",
session_id=sess_b,
request_id="r2",
existing_tools=None,
has_compressed_content_this_turn=False,
)
assert injected_b is False
assert not _has_ccr_tool(tools_b)
# A's next turn (no fresh CCR) MUST auto-inject (sticky).
tools_a, injected_a = apply_session_sticky_ccr_tool(
provider="anthropic",
session_id=sess_a,
request_id="r3",
existing_tools=None,
has_compressed_content_this_turn=False,
)
assert injected_a is True
assert _has_ccr_tool(tools_a)
def test_provider_isolation():
"""Same session_id under anthropic vs openai are tracked independently."""
session_id = "shared-session-id"
# Anthropic does CCR.
apply_session_sticky_ccr_tool(
provider="anthropic",
session_id=session_id,
request_id="r1",
existing_tools=None,
has_compressed_content_this_turn=True,
)
# OpenAI must NOT inherit anthropic's sticky state.
tools_o, injected_o = apply_session_sticky_ccr_tool(
provider="openai",
session_id=session_id,
request_id="r2",
existing_tools=None,
has_compressed_content_this_turn=False,
)
assert injected_o is False
assert not _has_ccr_tool(tools_o)
def test_existing_ccr_tool_in_client_list_skips_injection():
"""If client (e.g. via MCP) already provided headroom_retrieve, do not double up."""
session_id = "sess-with-mcp"
client_tool = {
"name": CCR_TOOL_NAME,
"description": "client-provided",
"input_schema": {"type": "object", "properties": {}, "required": []},
}
tools, injected = apply_session_sticky_ccr_tool(
provider="anthropic",
session_id=session_id,
request_id="r1",
existing_tools=[client_tool],
has_compressed_content_this_turn=True,
)
assert injected is False
# Tool list still contains the client's version (not duplicated).
names = [t.get("name") for t in tools]
assert names.count(CCR_TOOL_NAME) == 1
def test_no_session_id_falls_back_to_per_turn_decision():
"""WS / pre-session paths with no session_id behave per-turn."""
# No fresh CCR + no session_id → no inject.
tools, injected = apply_session_sticky_ccr_tool(
provider="anthropic",
session_id=None,
request_id="r1",
existing_tools=None,
has_compressed_content_this_turn=False,
)
assert injected is False
# Fresh CCR + no session_id → inject (per-turn).
tools, injected = apply_session_sticky_ccr_tool(
provider="anthropic",
session_id=None,
request_id="r2",
existing_tools=None,
has_compressed_content_this_turn=True,
)
assert injected is True
assert _has_ccr_tool(tools)
def test_history_references_ccr_tool_detects_both_provider_shapes():
# Anthropic: assistant tool_use content block.
anthropic_hist = [
{"role": "user", "content": "hi"},
{
"role": "assistant",
"content": [{"type": "tool_use", "name": CCR_TOOL_NAME, "id": "t1", "input": {}}],
},
]
assert history_references_ccr_tool(anthropic_hist) is True
# OpenAI: assistant tool_calls[].function.name.
openai_hist = [
{
"role": "assistant",
"tool_calls": [{"id": "c1", "function": {"name": CCR_TOOL_NAME, "arguments": "{}"}}],
}
]
assert history_references_ccr_tool(openai_hist) is True
# No reference, and malformed shapes must not crash.
assert history_references_ccr_tool([{"role": "user", "content": "hi"}]) is False
assert (
history_references_ccr_tool([{"content": None}, {"tool_calls": None}, "x", None]) is False
)
assert history_references_ccr_tool("not-a-list") is False
def test_sessionless_history_reference_forces_reinjection():
"""#2440: no session_id + no fresh compression, but history already
references headroom_retrieve → the tool definition MUST be re-injected,
otherwise the provider rejects the request (400 tool not found)."""
history = [
{
"role": "assistant",
"content": [{"type": "tool_use", "name": CCR_TOOL_NAME, "id": "t1", "input": {}}],
}
]
tools, injected = apply_session_sticky_ccr_tool(
provider="anthropic",
session_id=None,
request_id="r3",
existing_tools=None,
has_compressed_content_this_turn=False,
history_has_ccr_reference=history_references_ccr_tool(history),
)
assert injected is True
assert _has_ccr_tool(tools)
# No history reference and no fresh compression → still skip.
tools, injected = apply_session_sticky_ccr_tool(
provider="anthropic",
session_id=None,
request_id="r4",
existing_tools=None,
has_compressed_content_this_turn=False,
history_has_ccr_reference=False,
)
assert injected is False
# ─── Byte-stable tool definition ───────────────────────────────────────
# Snapshot of the canonical Anthropic CCR tool definition. Any change
# here MUST be deliberate — bumping the schema mid-session busts every
# active session's prompt cache (the tool list bytes are part of the
# cache key).
_ANTHROPIC_CCR_TOOL_SNAPSHOT_BYTES = (
b'{"name":"headroom_retrieve",'
b'"description":"Retrieve original uncompressed content that was '
b"compressed to save tokens. Use this when you need more data than "
b"what's shown in compressed tool results. The hash is provided in "
b'compression markers like [N items compressed... hash=abc123].",'
b'"input_schema":{"type":"object",'
b'"properties":{'
b'"hash":{"type":"string",'
b'"description":"Hash key from the compression marker '
b"(e.g., 'abc123' from hash=abc123)\"}"
b'},"required":["hash"]}}'
)
_OPENAI_CCR_TOOL_SNAPSHOT_BYTES = (
b'{"type":"function",'
b'"function":{"name":"headroom_retrieve",'
b'"description":"Retrieve original uncompressed content that was '
b"compressed to save tokens. Use this when you need more data than "
b"what's shown in compressed tool results. The hash is provided in "
b'compression markers like [N items compressed... hash=abc123].",'
b'"parameters":{"type":"object",'
b'"properties":{'
b'"hash":{"type":"string",'
b'"description":"Hash key from the compression marker '
b"(e.g., 'abc123' from hash=abc123)\"}"
b'},"required":["hash"]}}}'
)
def test_tool_definition_byte_stable():
"""Pin the canonical bytes of the Anthropic + OpenAI tool defs.
PR-B7 acceptance criterion: tool definition bytes are byte-stable.
Any future change to ``create_ccr_tool_definition`` must bump these
snapshots deliberately.
"""
anthropic_tool = create_ccr_tool_definition("anthropic")
canonical_anthropic = serialize_tool_definition_canonical(anthropic_tool)
assert canonical_anthropic == _ANTHROPIC_CCR_TOOL_SNAPSHOT_BYTES, (
f"Anthropic CCR tool definition bytes changed.\n"
f" expected: {_ANTHROPIC_CCR_TOOL_SNAPSHOT_BYTES!r}\n"
f" actual: {canonical_anthropic!r}\n"
f"If this change is intentional, update the snapshot in this "
f"test and ensure the prompt-cache implications are reviewed."
)
openai_tool = create_ccr_tool_definition("openai")
canonical_openai = serialize_tool_definition_canonical(openai_tool)
assert canonical_openai == _OPENAI_CCR_TOOL_SNAPSHOT_BYTES, (
f"OpenAI CCR tool definition bytes changed.\n"
f" expected: {_OPENAI_CCR_TOOL_SNAPSHOT_BYTES!r}\n"
f" actual: {canonical_openai!r}"
)
def test_sticky_replay_returns_byte_equal_tool_each_turn():
"""The bytes injected on turn 2 must equal the bytes injected on turn 1."""
session_id = "sess-byte-stable"
tools_1, _ = apply_session_sticky_ccr_tool(
provider="anthropic",
session_id=session_id,
request_id="r1",
existing_tools=None,
has_compressed_content_this_turn=True,
)
tools_2, _ = apply_session_sticky_ccr_tool(
provider="anthropic",
session_id=session_id,
request_id="r2",
existing_tools=None,
has_compressed_content_this_turn=False,
)
# Both tools lists should contain exactly one CCR tool with the
# same canonical bytes.
ccr_1 = next(t for t in tools_1 if t.get("name") == CCR_TOOL_NAME)
ccr_2 = next(t for t in tools_2 if t.get("name") == CCR_TOOL_NAME)
assert serialize_tool_definition_canonical(ccr_1) == serialize_tool_definition_canonical(ccr_2)
# ─── SessionCcrTracker unit coverage ────────────────────────────────────
def test_session_ccr_tracker_monotonic_has_done_ccr():
"""``has_done_ccr`` is monotonic — never flips back to False."""
tracker = SessionCcrTracker(max_sessions=10)
assert tracker.has_done_ccr("anthropic", "s1") is False
golden = serialize_tool_definition_canonical(create_ccr_tool_definition("anthropic"))
tracker.record_ccr_done("anthropic", "s1", golden)
assert tracker.has_done_ccr("anthropic", "s1") is True
# Re-record with a different golden_bytes — original bytes win
# (first-write wins) and flag stays True.
new_golden = b'{"name":"different","input_schema":{}}'
tracker.record_ccr_done("anthropic", "s1", new_golden)
assert tracker.has_done_ccr("anthropic", "s1") is True
assert tracker.get_golden_tool_bytes("anthropic", "s1") == golden
def test_session_ccr_tracker_lru_bound():
"""Tracker evicts oldest sessions once `max_sessions` is exceeded."""
tracker = SessionCcrTracker(max_sessions=3)
golden = b"{}"
for i in range(5):
tracker.record_ccr_done("anthropic", f"s{i}", golden)
# Only 3 most recent should remain.
assert tracker.active_sessions == 3
assert tracker.has_done_ccr("anthropic", "s0") is False
assert tracker.has_done_ccr("anthropic", "s1") is False
assert tracker.has_done_ccr("anthropic", "s4") is True
def test_session_ccr_tracker_reset_clears_state():
tracker = SessionCcrTracker(max_sessions=10)
tracker.record_ccr_done("anthropic", "s1", b"{}")
assert tracker.active_sessions == 1
tracker.reset()
assert tracker.active_sessions == 0
assert tracker.has_done_ccr("anthropic", "s1") is False
# ─── Per-request injector legacy path (PR-B7 backwards compat) ─────────
def test_ccrtoolinjector_session_has_done_ccr_kwarg():
"""``CCRToolInjector.inject_tool_definition`` accepts session_has_done_ccr."""
injector = CCRToolInjector(provider="anthropic", inject_tool=True)
# No fresh markers, no sticky flag → no inject (legacy behaviour).
tools, was = injector.inject_tool_definition(None)
assert was is False
assert tools == []
# No fresh markers, sticky flag set → inject (PR-B7 path).
tools, was = injector.inject_tool_definition(None, session_has_done_ccr=True)
assert was is True
assert _has_ccr_tool(tools)