web/agent_platform_port.py

@@ -57,6 +57,7 @@ from web.paperclip_client import (
     # ── raw imports: wrapped with telemetry below (state-affecting ops, #219) ──
     cancel_interaction as _cancel_interaction,
     cancel_run as _cancel_run,
+    escalate_issue as _escalate_issue,
     post_comment as _post_comment,
     reap_stale_interactions as _reap_stale_interactions,
     reset_agent_session as _reset_agent_session,
@@ -107,6 +108,12 @@ pc_post_comment = instrument(
 pc_cancel_interaction = instrument(
     "interaction.cancelled", keys=("issue_id", "interaction_id"),
 )(_cancel_interaction)
+# First-class escalation-to-chair (#218): the loop-safe alternative to leaving an
+# issue agent-owned+blocked. Emits a severity-tagged event so escalations are
+# countable per case in the same stream as the wakeups they replace.
+pc_escalate_issue = instrument(
+    "agent.escalated", keys=("issue_id", "severity", "company_id", "reason"),
+)(_escalate_issue)
 pc_reap_stale_interactions = instrument(
     "interaction.reaped", result_keys=("cancelled",),
 )(_reap_stale_interactions)
@@ -168,6 +175,7 @@ __all__ = [
     "pc_respond_to_interaction",
     "pc_cancel_interaction",
     "pc_reap_stale_interactions",
+    "pc_escalate_issue",
     # agent-run observability + control (live view + smart management)
     "pc_list_live_runs",
     "pc_get_run_log",

web/app.py

@@ -61,6 +61,7 @@ from web.agent_platform_port import (
     pc_cancel_run,
     pc_create_project,
     pc_create_workflow_issue,
+    pc_escalate_issue,
     pc_get_agents,
     pc_get_agents_for_case,
     pc_get_case_issues,
@@ -4651,6 +4652,30 @@ async def api_reset_case_agents(case_number: str):
     return result
 
 
+class EscalateRequest(BaseModel):
+    issue_id: str
+    severity: Literal["critical", "high", "medium"]
+    reason: str
+
+
+@app.post("/api/cases/{case_number}/agents/escalate")
+async def api_escalate_issue(case_number: str, req: EscalateRequest):
+    """Escalate a single stuck issue to the chair (#218).
+
+    The loop-safe alternative to leaving an issue agent-owned+blocked: hands the
+    issue to the human in one atomic transition (in_review + assignee_user_id)
+    and records a severity note, without re-waking any agent. Emits an
+    ``agent.escalated`` telemetry event via the Port.
+    """
+    issues = await pc_get_case_issues(case_number)
+    if not any(i["id"] == req.issue_id for i in issues):
+        raise HTTPException(404, f"Issue {req.issue_id} לא שייך לתיק {case_number}")
+    result = await pc_escalate_issue(req.issue_id, req.severity, req.reason)
+    if not result.get("ok"):
+        raise HTTPException(400, result.get("error", "ההסלמה נכשלה"))
+    return result
+
+
 # ── Settings: MCP Server Configuration ────────────────────────────
 #
 # Source of truth for legal-ai env vars is Coolify (see memory:

web/paperclip_client.py

@@ -856,6 +856,78 @@ async def reset_case_agents(case_number: str) -> dict:
     }
 
 
+ESCALATION_SEVERITIES = ("critical", "high", "medium")
+
+
+async def escalate_issue(
+    issue_id: str, severity: str, reason: str, company_id: str = "",
+) -> dict:
+    """First-class, severity-routed escalation of a stuck issue to the chair (#218).
+
+    Replaces the fragile manual "PATCH dance" (reassign + set in_review + open an
+    interaction) that repeatedly tripped Paperclip's recovery loops
+    (``source_scoped_recovery_action`` / ``stranded_assigned_issue`` /
+    ``issue_reopened_via_comment``; see memory reference_paperclip_recovery_loops).
+
+    Two effects in **one DB transaction**, mirroring the proven loop-safe path of
+    :func:`reset_case_agents` (raw SQL, not REST):
+
+    1. **Atomic human-owned transition** — a single ``UPDATE`` to the stable end
+       state ``{status:'in_review', assignee_agent_id:null,
+       assignee_user_id:CHAIM_USER_ID}`` (recovery-loops rule #7). Direct-DB on
+       purpose: it bypasses Paperclip's disposition resolver — the very machinery
+       whose multi-PATCH/`issue.released` behaviour *causes* the loops — so the
+       issue lands human-owned in one shot with no ``done→todo`` flip.
+    2. **Durable severity note** — an ``author_type='system'`` comment recording
+       severity + reason. System-authored on purpose: the ``route-pending-comments``
+       sweep routes only ``author_type='user'`` (chair) comments to the CEO, so a
+       system note is inert w.r.t. routing and will **not** re-wake an agent
+       (project_comment_delivery_guarantee). No wakeup is issued — the whole point
+       is to hand off to the human, not re-invoke an agent.
+
+    The ``agent.escalated`` telemetry event is emitted by the Port wrapper
+    (docs/spec/X15) — this is the loop-safe counterpart the CEO/analysts reach
+    for instead of leaving an issue agent-owned+blocked.
+    """
+    if severity not in ESCALATION_SEVERITIES:
+        return {
+            "ok": False,
+            "error": f"invalid severity {severity!r}; expected one of {ESCALATION_SEVERITIES}",
+        }
+
+    body = f"🚨 הסלמה [{severity}] לחיים\n\n{reason}"
+    conn = await asyncpg.connect(PAPERCLIP_DB_URL)
+    try:
+        async with conn.transaction():
+            row = await conn.fetchrow(
+                """UPDATE issues
+                      SET status='in_review', assignee_agent_id=null,
+                          assignee_user_id=$1, updated_at=now()
+                    WHERE id=$2::uuid
+                RETURNING id, identifier, company_id""",
+                CHAIM_USER_ID, issue_id,
+            )
+            if not row:
+                return {"ok": False, "error": f"issue {issue_id} not found"}
+            cid = company_id or str(row["company_id"])
+            await conn.execute(
+                """INSERT INTO issue_comments (id, company_id, issue_id, body, author_type)
+                   VALUES ($1::uuid, $2::uuid, $3::uuid, $4, 'system')""",
+                str(uuid.uuid4()), cid, issue_id, body,
+            )
+    finally:
+        await conn.close()
+
+    logger.info("Escalated issue %s to chair [severity=%s]", issue_id, severity)
+    return {
+        "ok": True,
+        "id": str(row["id"]),
+        "identifier": row["identifier"],
+        "severity": severity,
+        "status": "in_review",
+    }
+
+
 async def respond_to_interaction(
     issue_id: str, interaction_id: str, payload: dict,
 ) -> dict:

web/tests/test_escalate_issue.py

@@ -0,0 +1,118 @@
+"""Tests for #218 — paperclip_client.escalate_issue (loop-safe chair escalation).
+
+Verifies the primitive that replaces the fragile manual PATCH dance:
+- invalid severity is rejected before any DB work.
+- the happy path performs ONE atomic human-owned transition
+  (``status='in_review'``, ``assignee_user_id=CHAIM_USER_ID``) and records a
+  ``author_type='system'`` severity note carrying the reason.
+- **no wakeup / REST call is issued** — escalation hands off to the human, it
+  must never re-invoke an agent (that is what caused the recovery loops).
+- a missing issue reports ``ok:False`` and writes no comment.
+
+Uses a fake asyncpg connection — never touches the live Paperclip DB.
+"""
+
+from __future__ import annotations
+
+import asyncio
+import os
+import sys
+from pathlib import Path
+
+import pytest
+
+os.environ.setdefault("PAPERCLIP_DB_URL", "postgres://x:x@127.0.0.1:54329/paperclip")
+sys.path.insert(0, str(Path(__file__).resolve().parents[1]))  # web/
+
+pc = pytest.importorskip("paperclip_client", reason="web deps unavailable")
+
+
+class _FakeTxn:
+    async def __aenter__(self):
+        return None
+
+    async def __aexit__(self, *exc):
+        return False
+
+
+class _FakeConn:
+    def __init__(self, row):
+        self._row = row
+        self.updates: list[tuple] = []
+        self.inserts: list[tuple] = []
+        self.closed = False
+
+    def transaction(self):
+        return _FakeTxn()
+
+    async def fetchrow(self, query, *args):
+        self.updates.append((query, args))
+        return self._row
+
+    async def execute(self, query, *args):
+        self.inserts.append((query, args))
+
+    async def close(self):
+        self.closed = True
+
+
+@pytest.fixture
+def fake_db(monkeypatch):
+    """Patch asyncpg.connect + guard that no wakeup/REST is issued."""
+    conns: list[_FakeConn] = []
+    row = {"id": "iss-uuid", "identifier": "CMP-141", "company_id": "cmp-uuid"}
+    holder = {"row": row}
+
+    async def _connect(_url):
+        conn = _FakeConn(holder["row"])
+        conns.append(conn)
+        return conn
+
+    monkeypatch.setattr(pc.asyncpg, "connect", _connect)
+
+    async def _forbidden(*a, **k):  # any REST/wakeup would be a loop-risk
+        raise AssertionError("escalate_issue must not issue a wakeup/REST call")
+
+    monkeypatch.setattr(pc, "pc_request", _forbidden, raising=False)
+    return {"conns": conns, "holder": holder}
+
+
+def test_invalid_severity_rejected_before_db(fake_db):
+    result = asyncio.run(pc.escalate_issue("iss-1", "urgent", "boom"))
+    assert result["ok"] is False
+    assert "invalid severity" in result["error"]
+    assert fake_db["conns"] == []  # never connected
+
+
+def test_happy_path_atomic_transition_and_system_note(fake_db):
+    result = asyncio.run(
+        pc.escalate_issue("iss-uuid", "high", "analyst wedged on protocol parse")
+    )
+    assert result == {
+        "ok": True,
+        "id": "iss-uuid",
+        "identifier": "CMP-141",
+        "severity": "high",
+        "status": "in_review",
+    }
+    conn = fake_db["conns"][0]
+    # 1) one human-owned UPDATE with the chair user + in_review
+    (update_sql, update_args) = conn.updates[0]
+    assert "status='in_review'" in update_sql
+    assert "assignee_agent_id=null" in update_sql
+    assert update_args[0] == pc.CHAIM_USER_ID
+    assert update_args[1] == "iss-uuid"
+    # 2) a system-authored severity note carrying the reason
+    (insert_sql, insert_args) = conn.inserts[0]
+    assert "issue_comments" in insert_sql
+    assert "'system'" in insert_sql
+    assert "high" in insert_args[3] and "wedged on protocol parse" in insert_args[3]
+    assert conn.closed is True
+
+
+def test_missing_issue_reports_not_found_and_writes_no_comment(fake_db):
+    fake_db["holder"]["row"] = None
+    result = asyncio.run(pc.escalate_issue("ghost", "medium", "nope"))
+    assert result["ok"] is False and "not found" in result["error"]
+    conn = fake_db["conns"][0]
+    assert conn.inserts == []  # no comment on a non-existent issue