fix: add debug log and null company_id comment to webhook scheduling

web/app.py

@@ -20,7 +20,7 @@ sys.path.insert(0, str(Path(__file__).resolve().parent.parent / "mcp-server" / "
 
 import zipfile
 
-from fastapi import FastAPI, File, Form, HTTPException, UploadFile
+from fastapi import BackgroundTasks, FastAPI, File, Form, HTTPException, UploadFile
 from fastapi.responses import FileResponse, StreamingResponse
 from typing import Any, Literal
 from pydantic import BaseModel
@@ -44,7 +44,7 @@ from web.mcp_env_catalog import (
     normalize_for_compare,
 )
 from web.progress_store import ProgressStore
-from web.paperclip_api import pc_request
+from web.paperclip_api import emit_case_status_webhook, pc_request
 from web.paperclip_client import (
     COMPANIES as PAPERCLIP_COMPANIES,
     accept_interaction as pc_accept_interaction,
@@ -1337,8 +1337,12 @@ async def api_case_get(case_number: str):
 
 
 @app.put("/api/cases/{case_number}")
-async def api_case_update(case_number: str, req: CaseUpdateRequest):
+async def api_case_update(case_number: str, req: CaseUpdateRequest, background_tasks: BackgroundTasks):
     """Update case details."""
+    # Capture old status before the update so we can detect changes.
+    existing = await db.get_case_by_number(case_number)
+    old_status = (existing or {}).get("status", "")
+
     result = await cases_tools.case_update(
         case_number=case_number,
         status=req.status,
@@ -1351,10 +1355,30 @@ async def api_case_update(case_number: str, req: CaseUpdateRequest):
         expected_outcome=req.expected_outcome,
     )
     try:
-        return json.loads(result)
+        parsed = json.loads(result)
     except json.JSONDecodeError:
         raise HTTPException(404, result)
 
+    # Emit webhook when status changes (fire-and-forget via BackgroundTasks).
+    new_status = req.status
+    if new_status and old_status != new_status:
+        prefix = case_number[:1]
+        company_id = (
+            PAPERCLIP_COMPANIES["licensing"] if prefix == "1"
+            else PAPERCLIP_COMPANIES["betterment"] if prefix in ("8", "9")
+            else None
+        )
+        background_tasks.add_task(
+            emit_case_status_webhook,
+            case_number=case_number,
+            old_status=old_status,
+            new_status=new_status,
+            company_id=company_id,  # None is safe — plugin handles unknown company gracefully
+        )
+        logger.debug("webhook scheduled: case %s %s → %s", case_number, old_status, new_status)
+
+    return parsed
+
 
 @app.delete("/api/cases")
 async def api_case_delete(case_number: str, remove_files: bool = False):

web/paperclip_api.py

@@ -19,6 +19,7 @@ from __future__ import annotations
 
 import logging
 import os
+from datetime import datetime
 from typing import Any
 
 import httpx
@@ -81,3 +82,35 @@ async def pc_request(
     if raise_on_error:
         resp.raise_for_status()
     return resp
+
+
+async def emit_case_status_webhook(
+    case_number: str,
+    old_status: str,
+    new_status: str,
+    company_id: str | None = None,
+    run_id: str | None = None,
+) -> None:
+    """Notify the Paperclip plugin that a case status changed.
+
+    Fire-and-forget: logs errors but never raises, so callers aren't blocked.
+    """
+    try:
+        await pc_request(
+            "POST",
+            "/api/plugins/marcusgroup.legal-ai/webhooks/case-status",
+            json={
+                "caseNumber": case_number,
+                "oldStatus": old_status,
+                "newStatus": new_status,
+                "companyId": company_id,
+                "timestamp": datetime.utcnow().isoformat() + "Z",
+            },
+            run_id=run_id,
+            timeout=5.0,
+        )
+    except Exception as exc:
+        logger.warning(
+            "emit_case_status_webhook failed for case %s (%s → %s): %s",
+            case_number, old_status, new_status, exc,
+        )