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## Background
This PR consolidates and unifies context window management for the
CoPilot backend.
### Problem
The CoPilot backend had **two separate implementations** of context
window management:
1. **`service.py` → `_manage_context_window()`** - Chat service
streaming/continuation
2. **`prompt.py` → `compress_prompt()`** - Sync LLM blocks
This duplication led to inconsistent behavior, maintenance burden, and
duplicate code.
---
## Solution: Unified `compress_context()`
A single async function that handles both use cases:
| Caller | Usage | Behavior |
|--------|-------|----------|
| **Chat service** | `compress_context(msgs, client=openai_client)` |
Summarization → Truncation |
| **LLM blocks** | `compress_context(msgs, client=None)` | Truncation
only (no API call) |
---
## Strategy Order
| Step | Description | Runs When |
|------|-------------|-----------|
| **1. LLM Summarization** | Summarize old messages into single context
message, keep recent 15 | Only if `client` provided |
| **2. Content Truncation** | Progressively truncate message content
(8192→4096→...→128 tokens) | If still over limit |
| **3. Middle-out Deletion** | Delete messages one at a time from center
outward | If still over limit |
| **4. First/Last Trim** | Truncate system prompt and last message
content | Last resort |
### Why This Order?
1. **Summarization first** (if available) - Preserves semantic meaning
of old messages
2. **Content truncation before deletion** - Keeps all conversation
turns, just shorter
3. **Middle-out deletion** - More granular than dropping all old
messages at once
4. **First/last trim** - Only touch system prompt as last resort
---
## Key Fixes
| Issue | Before | After |
|-------|--------|-------|
| **Socket leak** | `AsyncOpenAI` client never closed | `async with`
context manager |
| **Timeout ignored** | `timeout=30` passed to `create()` (invalid) |
`client.with_options(timeout=30)` |
| **OpenAI tool messages** | Not truncated | Properly truncated |
| **Tool pair integrity** | OpenAI format only | Both OpenAI + Anthropic
formats |
---
## Tool Format Support
`_ensure_tool_pairs_intact()` now supports both formats:
### OpenAI Format
```python
# Assistant with tool_calls
{"role": "assistant", "tool_calls": [{"id": "call_1", ...}]}
# Tool response
{"role": "tool", "tool_call_id": "call_1", "content": "result"}
```
### Anthropic Format
```python
# Assistant with tool_use
{"role": "assistant", "content": [{"type": "tool_use", "id": "toolu_1", ...}]}
# Tool result
{"role": "user", "content": [{"type": "tool_result", "tool_use_id": "toolu_1", ...}]}
```
---
## Files Changed
| File | Change |
|------|--------|
| `backend/util/prompt.py` | +450 lines: Add `CompressResult`,
`compress_context()`, helpers |
| `backend/api/features/chat/service.py` | -380 lines: Remove duplicate,
use thin wrapper |
| `backend/blocks/llm.py` | Migrate `llm_call()` to use
`compress_context(client=None)` |
| `backend/util/prompt_test.py` | +400 lines: Comprehensive tests
(OpenAI + Anthropic) |
### Removed
- `compress_prompt()` - Replaced by `compress_context(client=None)`
- `_manage_context_window()` - Replaced by
`compress_context(client=openai_client)`
---
## API
```python
async def compress_context(
messages: list[dict],
target_tokens: int = 120_000,
*,
model: str = "gpt-4o",
client: AsyncOpenAI | None = None, # None = truncation only
keep_recent: int = 15,
reserve: int = 2_048,
start_cap: int = 8_192,
floor_cap: int = 128,
) -> CompressResult:
...
@dataclass
class CompressResult:
messages: list[dict]
token_count: int
was_compacted: bool
error: str | None = None
original_token_count: int = 0
messages_summarized: int = 0
messages_dropped: int = 0
```
---
## Tests Added
| Test Class | Coverage |
|------------|----------|
| `TestMsgTokens` | Token counting for regular messages, OpenAI tool
calls, Anthropic tool_use |
| `TestTruncateToolMessageContent` | OpenAI + Anthropic tool message
truncation |
| `TestEnsureToolPairsIntact` | OpenAI format (3 tests), Anthropic
format (3 tests), edge cases (3 tests) |
| `TestCompressContext` | No compression, truncation-only, tool pair
preservation, error handling |
---
## Checklist
- [x] Code follows project conventions
- [x] Linting passes (`poetry run format`)
- [x] Type checking passes (`pyright`)
- [x] Tests added for all new functions
- [x] Both OpenAI and Anthropic tool formats supported
- [x] Backward compatible behavior preserved
- [x] All review comments addressed