Add .docx attachment uploads to ClickUp tasks after press release generation

When a press release task completes, docx file paths are extracted from
the tool output and uploaded as attachments to the ClickUp task. The
completion comment now includes an attachment count note.

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>

CLAUDE.md

@@ -94,6 +94,7 @@ uv add --group test <package>
 - **ClickUp field mapping**: `Work Category` field (not `Task Type`) identifies task types like "Press Release", "Link Building". The `Client` field (not `Company`) holds the client name.
 - **Notifications**: All scheduler events go through `NotificationBus.push()`, never directly to a UI
 - **Tests**: Use `respx` to mock httpx calls, `tmp_db` fixture for isolated SQLite instances
+- **ClickUp attachments**: `ClickUpClient.upload_attachment()` uses module-level `httpx.post()` (not the shared client) for multipart uploads
 
 ## ClickUp Skill Mapping
 
@@ -109,7 +110,7 @@ skill_map:
       company_name: "Client"    # looks up "Client" custom field
 ```
 
-Task lifecycle: `to do` → discovered → approved/awaiting_approval → executing → completed/failed
+Task lifecycle: `to do` → discovered → approved/awaiting_approval → executing → completed/failed (+ attachments uploaded)
 
 ## Testing
 
@@ -122,6 +123,7 @@ Tests live in `tests/` and use pytest. All tests run offline with mocked APIs.
 - `test_email.py` — EmailClient SMTP send + attachments (mocked)
 - `test_docx_export.py` — Plain text → .docx formatting and file creation
 - `test_press_advantage.py` — Press Advantage API client, company parsing, link building, submit tool
+- `test_scheduler_helpers.py` — `_extract_docx_paths` regex extraction from tool output
 
 Fixtures in `conftest.py`: `tmp_db` (fresh SQLite), `sample_clickup_task_data` (realistic API response).
 

cheddahbot/clickup.py

@@ -4,6 +4,7 @@ from __future__ import annotations
 
 import logging
 from dataclasses import dataclass, field
+from pathlib import Path
 from typing import Any
 
 import httpx
@@ -170,6 +171,32 @@ class ClickUpClient:
             log.error("Failed to add comment to task %s: %s", task_id, e)
             return False
 
+    def upload_attachment(self, task_id: str, file_path: str | Path) -> bool:
+        """Upload a file attachment to a task.
+
+        Uses module-level httpx.post() instead of self._client because the
+        shared client sets Content-Type: application/json which conflicts
+        with multipart/form-data uploads.
+        """
+        fp = Path(file_path)
+        if not fp.exists():
+            log.warning("Attachment file not found: %s", fp)
+            return False
+        try:
+            with open(fp, "rb") as f:
+                resp = httpx.post(
+                    f"{BASE_URL}/task/{task_id}/attachment",
+                    headers={"Authorization": self._token},
+                    files={"attachment": (fp.name, f, "application/octet-stream")},
+                    timeout=60.0,
+                )
+            resp.raise_for_status()
+            log.info("Uploaded attachment %s to task %s", fp.name, task_id)
+            return True
+        except httpx.HTTPStatusError as e:
+            log.warning("Failed to upload attachment to task %s: %s", task_id, e)
+            return False
+
     def get_custom_fields(self, list_id: str) -> list[dict]:
         """Get custom fields for a list."""
         try:

cheddahbot/scheduler.py

@@ -4,6 +4,7 @@ from __future__ import annotations
 
 import json
 import logging
+import re
 import threading
 from datetime import datetime, timezone
 from typing import TYPE_CHECKING
@@ -20,6 +21,14 @@ log = logging.getLogger(__name__)
 
 HEARTBEAT_OK = "HEARTBEAT_OK"
 
+# Matches **Docx:** `path/to/file.docx` patterns in tool output
+_DOCX_PATH_RE = re.compile(r"\*\*Docx:\*\*\s*`([^`]+\.docx)`")
+
+
+def _extract_docx_paths(result: str) -> list[str]:
+    """Extract .docx file paths from a tool result string."""
+    return _DOCX_PATH_RE.findall(result)
+
 
 class Scheduler:
     def __init__(self, config: Config, db: Database, agent: Agent,
@@ -316,6 +325,16 @@ class Scheduler:
                     f"Task description: {state.get('custom_fields', {})}"
                 )
 
+            # Extract and upload any docx deliverables
+            docx_paths = _extract_docx_paths(result)
+            state["deliverable_paths"] = docx_paths
+            uploaded_count = 0
+            for path in docx_paths:
+                if client.upload_attachment(task_id, path):
+                    uploaded_count += 1
+                else:
+                    log.warning("Failed to upload %s for task %s", path, task_id)
+
             # Success
             state["state"] = "completed"
             state["completed_at"] = datetime.now(timezone.utc).isoformat()
@@ -323,10 +342,11 @@ class Scheduler:
 
             # Update ClickUp
             client.update_task_status(task_id, self.config.clickup.review_status)
+            attach_note = f"\n📎 {uploaded_count} file(s) attached." if uploaded_count else ""
             comment = (
                 f"✅ CheddahBot completed this task.\n\n"
                 f"Skill: {skill_name}\n"
-                f"Result:\n{result[:3000]}"
+                f"Result:\n{result[:3000]}{attach_note}"
             )
             client.add_comment(task_id, comment)
 

tests/test_clickup.py

@@ -3,7 +3,6 @@
 from __future__ import annotations
 
 import httpx
-import pytest
 import respx
 
 from cheddahbot.clickup import BASE_URL, ClickUpClient, ClickUpTask
@@ -256,6 +255,47 @@ class TestClickUpClient:
         assert fields[0]["name"] == "Task Type"
         client.close()
 
+    @respx.mock
+    def test_upload_attachment_success(self, tmp_path):
+        docx_file = tmp_path / "report.docx"
+        docx_file.write_bytes(b"fake docx content")
+
+        respx.post(f"{BASE_URL}/task/t1/attachment").mock(
+            return_value=httpx.Response(200, json={})
+        )
+
+        client = ClickUpClient(api_token="pk_test_123")
+        result = client.upload_attachment("t1", docx_file)
+
+        assert result is True
+        request = respx.calls.last.request
+        assert b"report.docx" in request.content
+        # Multipart upload should NOT have application/json content-type
+        assert "multipart/form-data" in request.headers.get("content-type", "")
+        client.close()
+
+    @respx.mock
+    def test_upload_attachment_http_failure(self, tmp_path):
+        docx_file = tmp_path / "report.docx"
+        docx_file.write_bytes(b"fake docx content")
+
+        respx.post(f"{BASE_URL}/task/t1/attachment").mock(
+            return_value=httpx.Response(403, json={"err": "forbidden"})
+        )
+
+        client = ClickUpClient(api_token="pk_test_123")
+        result = client.upload_attachment("t1", docx_file)
+
+        assert result is False
+        client.close()
+
+    def test_upload_attachment_file_not_found(self):
+        client = ClickUpClient(api_token="pk_test_123")
+        result = client.upload_attachment("t1", "/nonexistent/file.docx")
+
+        assert result is False
+        client.close()
+
     @respx.mock
     def test_auth_header_sent(self):
         respx.get(f"{BASE_URL}/list/list_1/task").mock(

tests/test_scheduler_helpers.py

@@ -0,0 +1,36 @@
+"""Tests for scheduler helper functions."""
+
+from __future__ import annotations
+
+from cheddahbot.scheduler import _extract_docx_paths
+
+
+class TestExtractDocxPaths:
+    def test_extracts_paths_from_realistic_output(self):
+        result = (
+            "Press releases generated successfully!\n\n"
+            "**Docx:** `output/press_releases/acme-corp-launch.docx`\n"
+            "**Docx:** `output/press_releases/acme-corp-expansion.docx`\n"
+            "Files saved to output/press_releases/"
+        )
+        paths = _extract_docx_paths(result)
+
+        assert len(paths) == 2
+        assert paths[0] == "output/press_releases/acme-corp-launch.docx"
+        assert paths[1] == "output/press_releases/acme-corp-expansion.docx"
+
+    def test_returns_empty_list_when_no_paths(self):
+        result = "Task completed successfully. No files generated."
+        paths = _extract_docx_paths(result)
+
+        assert paths == []
+
+    def test_only_matches_docx_extension(self):
+        result = (
+            "**Docx:** `report.docx`\n"
+            "**PDF:** `report.pdf`\n"
+            "**Docx:** `summary.txt`\n"
+        )
+        paths = _extract_docx_paths(result)
+
+        assert paths == ["report.docx"]