Add client delivery pipeline: Google Drive upload + Gmail drafts + reply tracking

Automates the PR delivery workflow: uploads .docx to Google Drive as Google Docs,
creates Gmail drafts with template-based emails and Ref: CU-<task_id> tracking tags,
and polls for client replies to update ClickUp tasks. Includes contact directory
with alias support, email template system, and manual CLI scripts for retries.

Co-Authored-By: Claude Opus 4.6 (1M context) <noreply@anthropic.com>

.gitignore

@@ -8,3 +8,5 @@ memory/*.md
 dist/
 build/
 .venv/
+credentials/
+

cheddahbot/config.py

@@ -131,6 +131,17 @@ class NtfyConfig:
     channels: list[NtfyChannelConfig] = field(default_factory=list)
 
 
+@dataclass
+class GoogleDriveConfig:
+    root_folder_id: str = ""
+    enabled: bool = False
+
+
+@dataclass
+class GmailApiConfig:
+    enabled: bool = False
+
+
 @dataclass
 class AgentConfig:
     """Per-agent configuration for multi-agent support."""
@@ -165,6 +176,8 @@ class Config:
     content: ContentConfig = field(default_factory=ContentConfig)
     timeouts: TimeoutConfig = field(default_factory=TimeoutConfig)
     ntfy: NtfyConfig = field(default_factory=NtfyConfig)
+    google_drive: GoogleDriveConfig = field(default_factory=GoogleDriveConfig)
+    gmail_api: GmailApiConfig = field(default_factory=GmailApiConfig)
     agents: list[AgentConfig] = field(default_factory=lambda: [AgentConfig()])
 
     # Derived paths
@@ -247,6 +260,18 @@ def load_config() -> Config:
                                 setattr(ch, k, v)
                         cfg.ntfy.channels.append(ch)
 
+        # Google Drive config
+        if "google_drive" in data and isinstance(data["google_drive"], dict):
+            for k, v in data["google_drive"].items():
+                if hasattr(cfg.google_drive, k):
+                    setattr(cfg.google_drive, k, v)
+
+        # Gmail API config
+        if "gmail_api" in data and isinstance(data["gmail_api"], dict):
+            for k, v in data["gmail_api"].items():
+                if hasattr(cfg.gmail_api, k):
+                    setattr(cfg.gmail_api, k, v)
+
         # Multi-agent configs
         if "agents" in data and isinstance(data["agents"], list):
             cfg.agents = []

cheddahbot/contacts.py

@@ -0,0 +1,133 @@
+"""Client contact directory parser for skills/companies.md."""
+
+from __future__ import annotations
+
+import logging
+from dataclasses import dataclass, field
+from pathlib import Path
+
+log = logging.getLogger(__name__)
+
+_COMPANIES_FILE = Path(__file__).resolve().parent.parent / "skills" / "companies.md"
+
+
+@dataclass
+class CompanyContact:
+    """Structured contact record for a client company."""
+
+    name: str
+    aliases: list[str] = field(default_factory=list)
+    executive: str = ""
+    email: str = ""
+    opening: str = ""
+    cc: str = ""
+    pa_org_id: int = 0
+    website: str = ""
+    gbp: str = ""
+
+    @property
+    def executive_first_name(self) -> str:
+        """Extract first name from executive field (e.g. 'Gary Hermsen, CEO' -> 'Gary')."""
+        if not self.executive:
+            return ""
+        return self.executive.split(",")[0].split()[0].strip()
+
+    @property
+    def cc_list(self) -> list[str]:
+        """Parse CC field into a list of email addresses."""
+        if not self.cc:
+            return []
+        return [addr.strip() for addr in self.cc.split(",") if addr.strip()]
+
+
+def parse_company_directory(path: Path | str = _COMPANIES_FILE) -> dict[str, CompanyContact]:
+    """Parse companies.md and return contacts keyed by lowercase company name.
+
+    Follows the same parsing pattern as press_release.py:_parse_company_data().
+    """
+    path = Path(path)
+    if not path.exists():
+        log.warning("Company directory not found: %s", path)
+        return {}
+
+    text = path.read_text(encoding="utf-8")
+    contacts: dict[str, CompanyContact] = {}
+    current: CompanyContact | None = None
+
+    for line in text.splitlines():
+        line = line.strip()
+        if line.startswith("## "):
+            if current:
+                contacts[current.name.lower()] = current
+            current = CompanyContact(name=line[3:].strip())
+        elif current:
+            _parse_field(current, line)
+
+    # Don't forget the last company
+    if current:
+        contacts[current.name.lower()] = current
+
+    log.info("Loaded %d company contacts from %s", len(contacts), path.name)
+    return contacts
+
+
+def _parse_field(contact: CompanyContact, line: str) -> None:
+    """Parse a single field line into the contact record."""
+    field_map = {
+        "- **Executive:**": "executive",
+        "- **Email:**": "email",
+        "- **Opening:**": "opening",
+        "- **CC:**": "cc",
+        "- **PA Org ID:**": "pa_org_id",
+        "- **Website:**": "website",
+        "- **GBP:**": "gbp",
+    }
+    # Handle Aliases specially (comma-separated list)
+    if line.startswith("- **Aliases:**"):
+        value = line[len("- **Aliases:**"):].strip()
+        contact.aliases = [a.strip() for a in value.split(",") if a.strip()]
+        return
+
+    for prefix, attr in field_map.items():
+        if line.startswith(prefix):
+            value = line[len(prefix):].strip()
+            if attr == "pa_org_id":
+                try:
+                    setattr(contact, attr, int(value))
+                except (ValueError, IndexError):
+                    pass
+            else:
+                setattr(contact, attr, value)
+            return
+
+
+def lookup_contact(company_name: str, contacts: dict[str, CompanyContact] | None = None) -> CompanyContact | None:
+    """Find a company contact by name with fuzzy matching.
+
+    Tries exact match on name and aliases, then substring containment.
+    """
+    if contacts is None:
+        contacts = parse_company_directory()
+
+    name_lower = company_name.lower().strip()
+
+    # Exact match on canonical name
+    if name_lower in contacts:
+        return contacts[name_lower]
+
+    # Exact match on aliases
+    for contact in contacts.values():
+        for alias in contact.aliases:
+            if alias.lower() == name_lower:
+                return contact
+
+    # Substring match on name and aliases
+    for key, contact in contacts.items():
+        if key in name_lower or name_lower in key:
+            return contact
+        for alias in contact.aliases:
+            alias_lower = alias.lower()
+            if alias_lower in name_lower or name_lower in alias_lower:
+                return contact
+
+    return None

cheddahbot/delivery.py

@@ -0,0 +1,130 @@
+"""Client delivery pipeline: Google Drive upload + Gmail draft creation."""
+
+from __future__ import annotations
+
+import logging
+from dataclasses import dataclass, field
+from pathlib import Path
+
+from .contacts import CompanyContact, lookup_contact, parse_company_directory
+from .email_templates import load_template, render_template
+
+log = logging.getLogger(__name__)
+
+
+@dataclass
+class DeliveryResult:
+    """Result of a client delivery attempt."""
+
+    doc_links: list[str] = field(default_factory=list)
+    draft_id: str = ""
+    errors: list[str] = field(default_factory=list)
+
+    @property
+    def success(self) -> bool:
+        return bool(self.draft_id) and not self.errors
+
+
+def deliver_to_client(
+    files: list[Path],
+    company_name: str,
+    task_id: str,
+    task_type: str,
+    ctx: dict | None = None,
+) -> DeliveryResult:
+    """Upload files to Google Drive and create a Gmail draft for the client.
+
+    Steps:
+        1. Look up client contact (email, opening, cc) from companies.md
+        2. Upload each .docx to Google Drive as a Google Doc
+        3. Load and render the email template for this task type
+        4. Create a Gmail draft with the rendered content
+
+    This function is designed to be non-fatal -- callers should wrap in try/except
+    so delivery failures don't break the main pipeline.
+    """
+    result = DeliveryResult()
+    config = ctx.get("config") if ctx else None
+
+    # 1. Look up client contact
+    contacts = parse_company_directory()
+    contact = lookup_contact(company_name, contacts)
+    if not contact:
+        result.errors.append("No contact found for company '%s'" % company_name)
+        log.warning("Delivery aborted: %s", result.errors[-1])
+        return result
+    if not contact.email:
+        result.errors.append(
+            "No email address for '%s' -- add Email field to skills/companies.md" % contact.name
+        )
+        log.warning("Delivery aborted: %s", result.errors[-1])
+        return result
+
+    # 2. Upload to Google Drive
+    drive_enabled = config and config.google_drive.enabled if config else False
+    if drive_enabled:
+        try:
+            from .google_drive import DriveClient
+
+            drive = DriveClient(root_folder_id=config.google_drive.root_folder_id)
+            folder_id = drive.ensure_client_folder(contact.name)
+
+            for file_path in files:
+                if not file_path.exists():
+                    result.errors.append("File not found: %s" % file_path)
+                    continue
+                file_id, web_link = drive.upload_as_google_doc(file_path, folder_id)
+                drive.set_link_sharing(file_id, role="commenter")
+                result.doc_links.append(web_link)
+        except Exception as e:
+            result.errors.append("Drive upload failed: %s" % e)
+            log.error("Drive upload failed: %s", e)
+    else:
+        log.info("Google Drive disabled, skipping upload")
+        # Fall back to listing local file paths
+        for file_path in files:
+            result.doc_links.append(str(file_path))
+
+    # 3. Load and render email template
+    template = load_template(task_type)
+    if not template:
+        result.errors.append("No email template for task type '%s'" % task_type)
+        log.warning("Delivery aborted: %s", result.errors[-1])
+        return result
+
+    # Build Google Doc links as a bullet list
+    links_text = "\n".join("- %s" % link for link in result.doc_links)
+
+    # Use the contact's custom opening, or fall back to "Hi {first_name},"
+    opening = contact.opening or ("Hi %s," % contact.executive_first_name)
+
+    context = {
+        "company_name": contact.name,
+        "opening": opening,
+        "executive_first_name": contact.executive_first_name,
+        "google_doc_links": links_text,
+        "task_id": task_id,
+    }
+    subject, body = render_template(template, context)
+
+    # 4. Create Gmail draft
+    gmail_enabled = config and config.gmail_api.enabled if config else False
+    if gmail_enabled:
+        try:
+            from .gmail_draft import GmailDraftClient
+
+            gmail = GmailDraftClient()
+            result.draft_id = gmail.create_draft(
+                to=contact.email,
+                subject=subject,
+                body=body,
+                cc=contact.cc_list or None,
+            )
+        except Exception as e:
+            result.errors.append("Gmail draft creation failed: %s" % e)
+            log.error("Gmail draft creation failed: %s", e)
+    else:
+        log.info("Gmail API disabled, skipping draft creation")
+        result.errors.append("Gmail API disabled -- draft not created")
+
+    return result

cheddahbot/email_templates.py

@@ -0,0 +1,91 @@
+"""Email template loader and renderer for client delivery emails."""
+
+from __future__ import annotations
+
+import logging
+from dataclasses import dataclass
+from pathlib import Path
+
+import yaml
+
+log = logging.getLogger(__name__)
+
+_TEMPLATES_DIR = Path(__file__).resolve().parent.parent / "skills" / "email_templates"
+
+
+@dataclass
+class EmailTemplate:
+    """Parsed email template with subject and body."""
+
+    task_type: str
+    subject_template: str
+    body_template: str
+
+
+def load_template(task_type: str, templates_dir: Path | str = _TEMPLATES_DIR) -> EmailTemplate | None:
+    """Load an email template matching the given task type.
+
+    Searches skills/email_templates/ for .md files with matching task_type in frontmatter.
+    """
+    templates_dir = Path(templates_dir)
+    if not templates_dir.exists():
+        log.warning("Email templates directory not found: %s", templates_dir)
+        return None
+
+    for md_file in templates_dir.glob("*.md"):
+        template = _parse_template_file(md_file)
+        if template and template.task_type.lower() == task_type.lower():
+            log.info("Loaded email template '%s' for task type '%s'", md_file.name, task_type)
+            return template
+
+    log.warning("No email template found for task type '%s'", task_type)
+    return None
+
+
+def _parse_template_file(path: Path) -> EmailTemplate | None:
+    """Parse a template .md file with YAML frontmatter."""
+    text = path.read_text(encoding="utf-8")
+
+    # Split frontmatter from body
+    if not text.startswith("---"):
+        return None
+
+    parts = text.split("---", 2)
+    if len(parts) < 3:
+        return None
+
+    try:
+        meta = yaml.safe_load(parts[1]) or {}
+    except yaml.YAMLError:
+        log.warning("Invalid YAML frontmatter in %s", path.name)
+        return None
+
+    task_type = meta.get("task_type", "")
+    subject = meta.get("subject", "")
+    body = parts[2].strip()
+
+    if not task_type or not body:
+        return None
+
+    return EmailTemplate(task_type=task_type, subject_template=subject, body_template=body)
+
+
+def render_template(template: EmailTemplate, context: dict) -> tuple[str, str]:
+    """Render a template with the given context dict.
+
+    Returns (subject, body). Uses str.format_map() for placeholder substitution.
+    Unknown placeholders are left as-is.
+    """
+    subject = _safe_format(template.subject_template, context)
+    body = _safe_format(template.body_template, context)
+    return subject, body
+
+
+def _safe_format(template: str, context: dict) -> str:
+    """Format a string template, leaving unknown placeholders intact."""
+
+    class SafeDict(dict):
+        def __missing__(self, key: str) -> str:
+            return "{" + key + "}"
+
+    return template.format_map(SafeDict(context))

cheddahbot/gmail_draft.py

@@ -0,0 +1,56 @@
+"""Gmail draft creation via Gmail API (OAuth2)."""
+
+from __future__ import annotations
+
+import base64
+import logging
+from email.mime.text import MIMEText
+
+from googleapiclient.discovery import build
+
+from .google_auth import get_credentials
+
+log = logging.getLogger(__name__)
+
+
+class GmailDraftClient:
+    """Create email drafts in Gmail via the API."""
+
+    def __init__(self):
+        creds = get_credentials()
+        self._service = build("gmail", "v1", credentials=creds)
+
+    def create_draft(
+        self,
+        to: str,
+        subject: str,
+        body: str,
+        cc: list[str] | None = None,
+    ) -> str:
+        """Create a draft email in the authenticated user's Gmail.
+
+        Args:
+            to: Recipient email address.
+            subject: Email subject line.
+            body: Plain text email body.
+            cc: Optional list of CC email addresses.
+
+        Returns:
+            The Gmail draft ID.
+        """
+        message = MIMEText(body)
+        message["to"] = to
+        message["subject"] = subject
+        if cc:
+            message["cc"] = ", ".join(cc)
+
+        raw = base64.urlsafe_b64encode(message.as_bytes()).decode("ascii")
+        draft = (
+            self._service.users()
+            .drafts()
+            .create(userId="me", body={"message": {"raw": raw}})
+            .execute()
+        )
+        draft_id = draft["id"]
+        log.info("Created Gmail draft %s (to=%s, subject=%s)", draft_id, to, subject)
+        return draft_id

cheddahbot/google_auth.py

@@ -0,0 +1,65 @@
+"""Google OAuth2 credential management for Gmail API and Google Drive API."""
+
+from __future__ import annotations
+
+import logging
+from pathlib import Path
+
+from google.auth.transport.requests import Request
+from google.oauth2.credentials import Credentials
+from google_auth_oauthlib.flow import InstalledAppFlow
+
+log = logging.getLogger(__name__)
+
+# All scopes requested upfront to avoid re-consent.
+SCOPES = [
+    "https://www.googleapis.com/auth/gmail.compose",  # Create drafts
+    "https://www.googleapis.com/auth/gmail.readonly",  # Read replies
+    "https://www.googleapis.com/auth/drive.file",  # Manage app-created files
+]
+
+_DEFAULT_CREDENTIALS_FILE = Path("credentials/gmail_credentials.json")
+_DEFAULT_TOKEN_FILE = Path("data/google_token.json")
+
+
+def get_credentials(
+    credentials_file: Path | str = _DEFAULT_CREDENTIALS_FILE,
+    token_file: Path | str = _DEFAULT_TOKEN_FILE,
+    scopes: list[str] | None = None,
+) -> Credentials:
+    """Return valid Google OAuth2 credentials, refreshing or re-authenticating as needed.
+
+    On first run, opens a browser for OAuth consent and stores the refresh token.
+    Subsequent runs use the stored token and refresh it automatically.
+    """
+    credentials_file = Path(credentials_file)
+    token_file = Path(token_file)
+    scopes = scopes or SCOPES
+
+    creds: Credentials | None = None
+
+    # Load existing token
+    if token_file.exists():
+        creds = Credentials.from_authorized_user_file(str(token_file), scopes)
+
+    # Refresh or re-authenticate
+    if creds and creds.expired and creds.refresh_token:
+        log.info("Refreshing expired Google token")
+        creds.refresh(Request())
+    elif not creds or not creds.valid:
+        if not credentials_file.exists():
+            raise FileNotFoundError(
+                "OAuth credentials file not found at %s. "
+                "Download it from Google Cloud Console -> APIs & Services -> Credentials."
+                % credentials_file
+            )
+        log.info("Starting Google OAuth consent flow (browser will open)")
+        flow = InstalledAppFlow.from_client_secrets_file(str(credentials_file), scopes)
+        creds = flow.run_local_server(port=0)
+
+    # Persist token for next run
+    token_file.parent.mkdir(parents=True, exist_ok=True)
+    with open(token_file, "w") as f:
+        f.write(creds.to_json())
+
+    return creds

cheddahbot/google_drive.py

@@ -0,0 +1,122 @@
+"""Google Drive client for uploading .docx files as Google Docs."""
+
+from __future__ import annotations
+
+import json
+import logging
+from pathlib import Path
+
+from googleapiclient.discovery import build
+from googleapiclient.http import MediaFileUpload
+
+from .google_auth import get_credentials
+
+log = logging.getLogger(__name__)
+
+_FOLDER_CACHE_FILE = Path("data/drive_folder_cache.json")
+_GOOGLE_DOC_MIME = "application/vnd.google-apps.document"
+_FOLDER_MIME = "application/vnd.google-apps.folder"
+
+
+class DriveClient:
+    """Upload .docx files to Google Drive as Google Docs with shareable links."""
+
+    def __init__(self, root_folder_id: str, cache_file: Path | str = _FOLDER_CACHE_FILE):
+        self._root_folder_id = root_folder_id
+        self._cache_file = Path(cache_file)
+        self._folder_cache = self._load_cache()
+        creds = get_credentials()
+        self._service = build("drive", "v3", credentials=creds)
+
+    def _load_cache(self) -> dict[str, str]:
+        """Load folder ID cache from disk."""
+        if self._cache_file.exists():
+            try:
+                return json.loads(self._cache_file.read_text())
+            except (json.JSONDecodeError, OSError):
+                log.warning("Corrupt drive folder cache, starting fresh")
+        return {}
+
+    def _save_cache(self) -> None:
+        """Persist folder ID cache to disk."""
+        self._cache_file.parent.mkdir(parents=True, exist_ok=True)
+        self._cache_file.write_text(json.dumps(self._folder_cache, indent=2))
+
+    def ensure_client_folder(self, company_name: str) -> str:
+        """Get or create a subfolder for the client under the root folder.
+
+        Returns the folder ID.
+        """
+        cache_key = company_name.strip().lower()
+        if cache_key in self._folder_cache:
+            return self._folder_cache[cache_key]
+
+        # Check if folder already exists in Drive
+        query = (
+            f"name = '{company_name}' and "
+            f"'{self._root_folder_id}' in parents and "
+            f"mimeType = '{_FOLDER_MIME}' and trashed = false"
+        )
+        results = self._service.files().list(q=query, fields="files(id, name)").execute()
+        files = results.get("files", [])
+
+        if files:
+            folder_id = files[0]["id"]
+            log.info("Found existing Drive folder for '%s': %s", company_name, folder_id)
+        else:
+            # Create new folder
+            metadata = {
+                "name": company_name,
+                "mimeType": _FOLDER_MIME,
+                "parents": [self._root_folder_id],
+            }
+            folder = self._service.files().create(body=metadata, fields="id").execute()
+            folder_id = folder["id"]
+            log.info("Created Drive folder for '%s': %s", company_name, folder_id)
+
+        self._folder_cache[cache_key] = folder_id
+        self._save_cache()
+        return folder_id
+
+    def upload_as_google_doc(
+        self, local_path: Path | str, folder_id: str
+    ) -> tuple[str, str]:
+        """Upload a .docx file to Google Drive, converting to Google Doc.
+
+        Returns (file_id, web_view_link).
+        """
+        local_path = Path(local_path)
+        if not local_path.exists():
+            raise FileNotFoundError("File not found: %s" % local_path)
+
+        metadata = {
+            "name": local_path.stem,
+            "parents": [folder_id],
+            "mimeType": _GOOGLE_DOC_MIME,
+        }
+        media = MediaFileUpload(
+            str(local_path),
+            mimetype="application/vnd.openxmlformats-officedocument.wordprocessingml.document",
+        )
+        result = (
+            self._service.files()
+            .create(body=metadata, media_body=media, fields="id, webViewLink")
+            .execute()
+        )
+        file_id = result["id"]
+        web_link = result["webViewLink"]
+        log.info("Uploaded '%s' as Google Doc: %s", local_path.name, web_link)
+        return file_id, web_link
+
+    def set_link_sharing(self, file_id: str, role: str = "commenter") -> None:
+        """Make a file accessible to anyone with the link.
+
+        Args:
+            file_id: Google Drive file ID.
+            role: Permission role - 'reader', 'commenter', or 'writer'.
+        """
+        permission = {"type": "anyone", "role": role}
+        self._service.permissions().create(
+            fileId=file_id, body=permission, fields="id"
+        ).execute()
+        log.info("Set link sharing (role=%s) on file %s", role, file_id)

cheddahbot/tools/press_release.py

@@ -878,6 +878,34 @@ def write_press_releases(
         finally:
             cu_client.close()
 
+    # ── Client delivery: Drive upload + Gmail draft ──────────────────
+    if clickup_task_id and docx_files:
+        try:
+            from ..delivery import deliver_to_client
+
+            delivery_result = deliver_to_client(
+                files=[Path(f) for f in docx_files],
+                company_name=company_name,
+                task_id=clickup_task_id,
+                task_type="Press Release",
+                ctx=ctx,
+            )
+            output_parts.append("\n## Client Delivery\n")
+            if delivery_result.doc_links:
+                output_parts.append(
+                    "- Google Docs: " + ", ".join(delivery_result.doc_links)
+                )
+            if delivery_result.draft_id:
+                output_parts.append(
+                    "- Gmail draft created (ID: %s)" % delivery_result.draft_id
+                )
+            if delivery_result.errors:
+                for err in delivery_result.errors:
+                    output_parts.append("- Warning: %s" % err)
+        except Exception as e:
+            log.warning("Client delivery failed: %s", e)
+            output_parts.append("\n## Client Delivery\n- Failed: %s" % e)
+
     return "\n".join(output_parts)
 
 

config.yaml

@@ -139,6 +139,15 @@ ntfy:
       priority: high
       tags: clipboard
 
+# Google Drive (for client deliverables)
+google_drive:
+  root_folder_id: ""  # Set to your "CheddahBot Deliverables" folder ID
+  enabled: false
+
+# Gmail API (for draft creation and reply tracking)
+gmail_api:
+  enabled: false
+
 # Multi-agent configuration
 # Each agent gets its own personality, tool whitelist, and memory scope.
 # The first agent is the default. Omit this section for single-agent mode.

pyproject.toml

@@ -19,6 +19,8 @@ dependencies = [
     "jinja2>=3.1.6",
     "python-multipart>=0.0.22",
     "sse-starlette>=3.3.3",
+    "google-auth-oauthlib>=1.3.1",
+    "google-api-python-client>=2.194.0",
 ]
 
 [build-system]

scripts/check_gmail_replies.py

@@ -0,0 +1,253 @@
+"""Poll Gmail for client replies and update ClickUp tasks.
+
+Searches for email threads containing "Ref: CU-<task_id>" where the latest
+message is from someone other than the bot. Posts the reply text as a ClickUp
+comment and moves the task to "After Client Feedback" status.
+
+Usage:
+    uv run python scripts/check_gmail_replies.py              # normal run
+    uv run python scripts/check_gmail_replies.py --dry-run    # preview only
+    uv run python scripts/check_gmail_replies.py --since 48   # look back 48 hours
+"""
+
+from __future__ import annotations
+
+import argparse
+import base64
+import json
+import logging
+import os
+import re
+import sys
+from datetime import UTC, datetime, timedelta
+from email.utils import parseaddr
+from pathlib import Path
+
+sys.path.insert(0, str(Path(__file__).resolve().parent.parent))
+
+from dotenv import load_dotenv
+
+load_dotenv()
+
+from googleapiclient.discovery import build  # noqa: E402
+
+from cheddahbot.clickup import ClickUpClient  # noqa: E402
+from cheddahbot.google_auth import get_credentials  # noqa: E402
+
+logging.basicConfig(level=logging.INFO, format="%(asctime)s - %(levelname)s - %(message)s")
+log = logging.getLogger(__name__)
+
+STATE_FILE = Path("data/gmail_sync_state.json")
+REF_PATTERN = re.compile(r"Ref:\s*CU-(\w+)")
+AFTER_FEEDBACK_STATUS = "after client feedback"
+
+
+def _load_state() -> dict:
+    """Load sync state from disk."""
+    if STATE_FILE.exists():
+        try:
+            return json.loads(STATE_FILE.read_text())
+        except (json.JSONDecodeError, OSError):
+            log.warning("Corrupt state file, starting fresh")
+    return {}
+
+
+def _save_state(state: dict) -> None:
+    """Persist sync state to disk."""
+    STATE_FILE.parent.mkdir(parents=True, exist_ok=True)
+    STATE_FILE.write_text(json.dumps(state, indent=2))
+
+
+def _get_message_body(payload: dict) -> str:
+    """Extract plain text body from a Gmail message payload."""
+    # Simple single-part message
+    if payload.get("mimeType") == "text/plain" and "data" in payload.get("body", {}):
+        return base64.urlsafe_b64decode(payload["body"]["data"]).decode("utf-8", errors="replace")
+
+    # Multipart message -- find the text/plain part
+    for part in payload.get("parts", []):
+        if part.get("mimeType") == "text/plain" and "data" in part.get("body", {}):
+            return base64.urlsafe_b64decode(part["body"]["data"]).decode("utf-8", errors="replace")
+        # Nested multipart
+        if part.get("parts"):
+            result = _get_message_body(part)
+            if result:
+                return result
+
+    return ""
+
+
+def _extract_reply_text(body: str) -> str:
+    """Extract just the new reply content (above the quoted text).
+
+    Looks for common reply markers like "On ... wrote:" and takes everything above.
+    Falls back to the full body if no marker is found.
+    """
+    # Common reply markers
+    markers = [
+        r"\nOn .+ wrote:\s*\n",  # Gmail-style
+        r"\n-{3,}\s*Original Message\s*-{3,}",  # Outlook-style
+        r"\nFrom:\s+.+\nSent:\s+",  # Outlook-style
+    ]
+    for marker in markers:
+        match = re.search(marker, body, re.IGNORECASE)
+        if match:
+            reply = body[: match.start()].strip()
+            if reply:
+                return reply
+
+    return body.strip()
+
+
+def main():
+    parser = argparse.ArgumentParser(description="Check Gmail for client replies")
+    parser.add_argument("--dry-run", action="store_true", help="Preview without making changes")
+    parser.add_argument("--since", type=int, help="Look back N hours (overrides state file)")
+    parser.add_argument("--verbose", action="store_true", help="Enable debug logging")
+    args = parser.parse_args()
+
+    if args.verbose:
+        logging.getLogger().setLevel(logging.DEBUG)
+
+    # Determine lookback time
+    state = _load_state()
+    if args.since:
+        since = datetime.now(UTC) - timedelta(hours=args.since)
+    elif "last_check" in state:
+        since = datetime.fromisoformat(state["last_check"])
+    else:
+        since = datetime.now(UTC) - timedelta(hours=24)
+
+    processed_ids = set(state.get("processed_message_ids", []))
+    since_str = since.strftime("%Y/%m/%d")
+
+    log.info("Checking for replies since %s", since.isoformat())
+
+    # Authenticate and build Gmail service
+    creds = get_credentials()
+    gmail = build("gmail", "v1", credentials=creds)
+
+    # Get the authenticated user's email for filtering out our own messages
+    profile = gmail.users().getProfile(userId="me").execute()
+    my_email = profile.get("emailAddress", "").lower()
+    log.info("Authenticated as %s", my_email)
+
+    # Search for threads with Ref: CU- pattern
+    query = 'in:inbox "Ref: CU-" after:%s' % since_str
+    log.info("Gmail search query: %s", query)
+
+    threads_result = gmail.users().threads().list(userId="me", q=query).execute()
+    threads = threads_result.get("threads", [])
+    log.info("Found %d candidate threads", len(threads))
+
+    # Initialize ClickUp client
+    clickup_token = os.environ.get("CLICKUP_API_TOKEN", "")
+    cu_client = ClickUpClient(api_token=clickup_token) if clickup_token else None
+
+    stats = {"replies_found": 0, "comments_posted": 0, "statuses_updated": 0, "errors": 0}
+
+    for thread_info in threads:
+        thread_id = thread_info["id"]
+        thread = gmail.users().threads().get(userId="me", id=thread_id).execute()
+        messages = thread.get("messages", [])
+
+        if not messages:
+            continue
+
+        # Get the latest message in the thread
+        latest = messages[-1]
+        msg_id = latest["id"]
+
+        # Skip if already processed
+        if msg_id in processed_ids:
+            continue
+
+        # Check if the latest message is from someone else (not us)
+        headers = {h["name"].lower(): h["value"] for h in latest.get("payload", {}).get("headers", [])}
+        from_addr = parseaddr(headers.get("from", ""))[1].lower()
+        if from_addr == my_email:
+            continue  # Our own message, skip
+
+        # Extract the body and find the Ref tag
+        body = _get_message_body(latest.get("payload", {}))
+        if not body:
+            # Check earlier messages in thread for the Ref tag
+            for msg in reversed(messages[:-1]):
+                body_check = _get_message_body(msg.get("payload", {}))
+                ref_match = REF_PATTERN.search(body_check)
+                if ref_match:
+                    body = _get_message_body(latest.get("payload", {}))
+                    task_id = ref_match.group(1)
+                    break
+            else:
+                continue
+        else:
+            # Search the entire thread for the Ref tag (might be in quoted text or earlier message)
+            task_id = None
+            for msg in messages:
+                msg_body = _get_message_body(msg.get("payload", {}))
+                ref_match = REF_PATTERN.search(msg_body)
+                if ref_match:
+                    task_id = ref_match.group(1)
+                    break
+
+            if not task_id:
+                continue
+
+        reply_text = _extract_reply_text(body)
+        reply_date = headers.get("date", "unknown")
+        subject = headers.get("subject", "(no subject)")
+
+        stats["replies_found"] += 1
+        print("\n--- Reply Found ---")
+        print("  From: %s" % from_addr)
+        print("  Subject: %s" % subject)
+        print("  Date: %s" % reply_date)
+        print("  Task: CU-%s" % task_id)
+        print("  Reply preview: %s..." % reply_text[:200])
+
+        if not args.dry_run and cu_client:
+            # Post comment to ClickUp
+            try:
+                comment = "Email reply from %s (%s):\n\n%s" % (from_addr, reply_date, reply_text)
+                cu_client.add_comment(task_id, comment)
+                stats["comments_posted"] += 1
+                print("  -> Comment posted to ClickUp")
+            except Exception as e:
+                log.error("Failed to post comment for task %s: %s", task_id, e)
+                stats["errors"] += 1
+                continue  # Don't update status or mark processed if comment failed
+
+            # Update task status
+            try:
+                cu_client.update_task_status(task_id, AFTER_FEEDBACK_STATUS)
+                stats["statuses_updated"] += 1
+                print("  -> Status set to '%s'" % AFTER_FEEDBACK_STATUS)
+            except Exception as e:
+                log.error("Failed to update status for task %s: %s", task_id, e)
+                stats["errors"] += 1
+
+        # Mark as processed
+        processed_ids.add(msg_id)
+
+    # Save state
+    if not args.dry_run:
+        state["last_check"] = datetime.now(UTC).isoformat()
+        state["processed_message_ids"] = list(processed_ids)[-500:]  # Keep last 500
+        _save_state(state)
+
+    print("\n--- Summary ---")
+    print("  Replies found: %d" % stats["replies_found"])
+    if not args.dry_run:
+        print("  Comments posted: %d" % stats["comments_posted"])
+        print("  Statuses updated: %d" % stats["statuses_updated"])
+        print("  Errors: %d" % stats["errors"])
+    else:
+        print("  (dry-run -- no changes made)")
+
+    if cu_client:
+        cu_client.close()
+
+
+if __name__ == "__main__":
+    main()

scripts/create_client_draft.py

@@ -0,0 +1,77 @@
+"""Create a Gmail draft for client delivery (manual/retry use).
+
+Usage:
+    uv run python scripts/create_client_draft.py --company "McCormick Industries" \\
+        --files data/generated/press_releases/mccormick/file1.docx \\
+        --task-id abc123 --type "Press Release"
+"""
+
+from __future__ import annotations
+
+import argparse
+import logging
+import sys
+from pathlib import Path
+
+sys.path.insert(0, str(Path(__file__).resolve().parent.parent))
+
+from dotenv import load_dotenv
+
+load_dotenv()
+
+from cheddahbot.config import load_config  # noqa: E402
+from cheddahbot.delivery import deliver_to_client  # noqa: E402
+
+logging.basicConfig(level=logging.INFO, format="%(asctime)s - %(levelname)s - %(message)s")
+
+
+def main():
+    parser = argparse.ArgumentParser(description="Create client delivery draft email")
+    parser.add_argument("--company", required=True, help="Company name (must match companies.md)")
+    parser.add_argument("--files", nargs="+", required=True, help="Paths to .docx files")
+    parser.add_argument("--task-id", required=True, help="ClickUp task ID for tracking")
+    parser.add_argument("--type", default="Press Release", help="Task type (default: Press Release)")
+    args = parser.parse_args()
+
+    config = load_config()
+    ctx = {"config": config}
+
+    file_paths = [Path(f) for f in args.files]
+    for f in file_paths:
+        if not f.exists():
+            print("ERROR: File not found: %s" % f)
+            sys.exit(1)
+
+    print("Creating client delivery draft...")
+    print("  Company: %s" % args.company)
+    print("  Files: %s" % [str(f) for f in file_paths])
+    print("  Task ID: %s" % args.task_id)
+    print("  Type: %s" % args.type)
+    print()
+
+    result = deliver_to_client(
+        files=file_paths,
+        company_name=args.company,
+        task_id=args.task_id,
+        task_type=args.type,
+        ctx=ctx,
+    )
+
+    if result.doc_links:
+        print("Google Doc links:")
+        for link in result.doc_links:
+            print("  - %s" % link)
+
+    if result.draft_id:
+        print("\nGmail draft created: %s" % result.draft_id)
+
+    if result.errors:
+        print("\nErrors:")
+        for err in result.errors:
+            print("  - %s" % err)
+
+    print("\nDone." if result.success else "\nCompleted with issues.")
+
+
+if __name__ == "__main__":
+    main()

scripts/fix_tier_one_flags.py

@@ -0,0 +1,64 @@
+"""Fix CLIFlags custom field: replace --tier-one with --tier-1 on all non-closed tasks.
+
+Usage:
+    uv run python scripts/fix_tier_one_flags.py          # dry-run (default)
+    uv run python scripts/fix_tier_one_flags.py --apply   # actually update tasks
+"""
+
+from __future__ import annotations
+
+import argparse
+import os
+import re
+import sys
+from pathlib import Path
+
+sys.path.insert(0, str(Path(__file__).resolve().parent.parent))
+
+from dotenv import load_dotenv
+
+from cheddahbot.clickup import ClickUpClient
+
+load_dotenv()
+
+
+def main():
+    parser = argparse.ArgumentParser(description="Fix --tier-one -> --tier-1 in CLIFlags")
+    parser.add_argument("--apply", action="store_true", help="Actually update tasks (default: dry-run)")
+    args = parser.parse_args()
+
+    token = os.environ["CLICKUP_API_TOKEN"]
+    space_id = os.environ["CLICKUP_SPACE_ID"]
+
+    client = ClickUpClient(api_token=token)
+
+    print(f"Fetching all non-closed tasks from space {space_id}...")
+    tasks = client.get_tasks_from_space(space_id)
+    print(f"Found {len(tasks)} tasks total")
+
+    fix_count = 0
+    for task in tasks:
+        cli_flags = task.custom_fields.get("CLIFlags", "") or ""
+        if "--tier-one" not in cli_flags:
+            continue
+
+        new_flags = cli_flags.replace("--tier-one", "--tier-1")
+        fix_count += 1
+        print(f"  [{task.id}] {task.name}")
+        print(f"    OLD: {cli_flags}")
+        print(f"    NEW: {new_flags}")
+
+        if args.apply:
+            ok = client.set_custom_field_by_name(task.id, "CLIFlags", new_flags)
+            if ok:
+                print("    -> Updated")
+            else:
+                print("    -> FAILED to update")
+
+    print(f"\n{'Updated' if args.apply else 'Would update'} {fix_count} tasks")
+    if not args.apply and fix_count > 0:
+        print("Run with --apply to make changes")
+
+
+if __name__ == "__main__":
+    main()

scripts/google_auth_setup.py

@@ -0,0 +1,67 @@
+"""One-time Google OAuth2 setup script.
+
+Usage:
+    uv run python scripts/google_auth_setup.py
+    uv run python scripts/google_auth_setup.py --test-drive FOLDER_ID
+"""
+
+from __future__ import annotations
+
+import argparse
+import sys
+from pathlib import Path
+
+sys.path.insert(0, str(Path(__file__).resolve().parent.parent))
+
+from dotenv import load_dotenv
+
+load_dotenv()
+
+from cheddahbot.google_auth import get_credentials  # noqa: E402
+
+
+def main():
+    parser = argparse.ArgumentParser(description="Google OAuth2 setup for CheddahBot")
+    parser.add_argument(
+        "--test-drive",
+        metavar="FOLDER_ID",
+        help="Test Drive access by listing files in the given folder",
+    )
+    args = parser.parse_args()
+
+    print("Authenticating with Google (browser will open on first run)...")
+    creds = get_credentials()
+    print("Authentication successful. Token saved to data/google_token.json")
+
+    # Show granted scopes
+    if hasattr(creds, "scopes") and creds.scopes:
+        print("\nGranted scopes:")
+        for scope in creds.scopes:
+            print("  - %s" % scope)
+
+    if args.test_drive:
+        from googleapiclient.discovery import build
+
+        service = build("drive", "v3", credentials=creds)
+        results = (
+            service.files()
+            .list(
+                q="'%s' in parents and trashed = false" % args.test_drive,
+                fields="files(id, name, mimeType)",
+                pageSize=10,
+            )
+            .execute()
+        )
+        files = results.get("files", [])
+        if files:
+            print("\nFiles in folder %s:" % args.test_drive)
+            for f in files:
+                print("  - %s (%s)" % (f["name"], f["mimeType"]))
+        else:
+            print("\nFolder %s is empty or not accessible." % args.test_drive)
+
+    print("\nSetup complete.")
+
+
+if __name__ == "__main__":
+    main()

skills/companies.md

@@ -1,7 +1,11 @@
 # Company Directory
 
 ## McCormick Industries
+- **Aliases:** McCormick
 - **Executive:** Gary Hermsen, CEO
+- **Email:**
+- **Opening:**
+- **CC:**
 - **PA Org ID:** 19413
 - **Website:**
 - **GBP:**
@@ -25,6 +29,7 @@
 - **GBP:**
 
 ## Metal Craft
+- **Aliases:** Metal Craft Spinning
 - **Executive:** Kyle, Vice President
 - **PA Org ID:** 19800
 - **Website:**
@@ -37,18 +42,21 @@
 - **GBP:**
 
 ## MOD-TRONIC Instruments Limited
+- **Aliases:** Modtronic
 - **Executive:** Steven Ruple, President
 - **PA Org ID:** 19901
 - **Website:**
 - **GBP:**
 
 ## Krueger Sentry Gauge
+- **Aliases:** Krueger Sentry
 - **Executive:** Lee Geurts, Vice President
 - **PA Org ID:** 20862
 - **Website:**
 - **GBP:**
 
 ## Chapter 2 Incorporated
+- **Aliases:** Chapter 2
 - **Executive:** Kyle Johnston, Senior Engineer
 - **PA Org ID:** 19517
 - **Website:**
@@ -61,12 +69,14 @@
 - **GBP:**
 
 ## Renown Electric Motors & Repairs Inc.
+- **Aliases:** Renown Electric
 - **Executive:** Jeff Collins, Partner
 - **PA Org ID:** 19546
 - **Website:**
 - **GBP:**
 
 ## RPM Industrial Rubber Parts
+- **Aliases:** RPM Rubber
 - **Executive:** Mike McNeil, Vice President
 - **PA Org ID:** 19395
 - **Website:** https://www.rpmrubberparts.com/
@@ -91,6 +101,7 @@
 - **GBP:**
 
 ## Axiomatic Global Electronic Solutions
+- **Aliases:** Axiomatic
 - **Executive:** Amanda Wilkins, Chief Marketing Officer
 - **PA Org ID:** 19633
 - **Website:**
@@ -103,6 +114,7 @@
 - **GBP:**
 
 ## ELIS Manufacturing and Packaging Solutions Inc.
+- **Aliases:** ELIS Packaging
 - **Executive:** Keith Vinson, Chief Executive Officer
 - **PA Org ID:** 19656
 - **Website:**
@@ -115,12 +127,14 @@
 - **GBP:**
 
 ## FZE Manufacturing
+- **Aliases:** FZE Manufacturing Solutions
 - **Executive:** Doug Pribyl, CEO
 - **PA Org ID:** 22377
 - **Website:**
 - **GBP:**
 
 ## Machine Specialty & Manufacturing (MSM)
+- **Aliases:** Machine Specialty
 - **Executive:** Max Hutson, Vice President of Operations
 - **PA Org ID:** 19418
 - **Website:**
@@ -139,6 +153,8 @@
 - **GBP:** https://maps.app.goo.gl/wBgq49g3Xs4Y91zP9
 
 ## EVR Products
+- **Aliases:** Elasto Valve Rubber (EVR)
 - **Executive:** Gary Waldick, Vice President of EVR Products
-- **Website:**
-- **GBP:**
+- **Website:** evrproducts.com
+- **GBP:**  https://maps.app.goo.gl/bwaEWE5hCkgni1gk6
+- The company is a custom rubber products supplier based in Sudbury, Ontario

skills/email_templates/press_release.md

@@ -0,0 +1,16 @@
+---
+task_type: Press Release
+subject: "Press Releases Ready for Review - {company_name}"
+---
+{opening}
+
+We have prepared press releases for {company_name} and they are ready for your review. Please find them linked below:
+
+{google_doc_links}
+
+Please let us know if you would like any changes or if these are approved for distribution.
+
+Thank you,
+Bryan
+
+Ref: CU-{task_id}

uv.lock

@@ -315,6 +315,165 @@ wheels = [
     { url = "https://files.pythonhosted.org/packages/e6/ad/3cc14f097111b4de0040c83a525973216457bbeeb63739ef1ed275c1c021/certifi-2026.1.4-py3-none-any.whl", hash = "sha256:9943707519e4add1115f44c2bc244f782c0249876bf51b6599fee1ffbedd685c", size = 152900, upload-time = "2026-01-04T02:42:40.15Z" },
 ]
 
+[[package]]
+name = "cffi"
+version = "2.0.0"
+source = { registry = "https://pypi.org/simple" }
+dependencies = [
+    { name = "pycparser", marker = "implementation_name != 'PyPy'" },
+]
+sdist = { url = "https://files.pythonhosted.org/packages/eb/56/b1ba7935a17738ae8453301356628e8147c79dbb825bcbc73dc7401f9846/cffi-2.0.0.tar.gz", hash = "sha256:44d1b5909021139fe36001ae048dbdde8214afa20200eda0f64c068cac5d5529", size = 523588, upload-time = "2025-09-08T23:24:04.541Z" }
+wheels = [
+    { url = "https://files.pythonhosted.org/packages/12/4a/3dfd5f7850cbf0d06dc84ba9aa00db766b52ca38d8b86e3a38314d52498c/cffi-2.0.0-cp311-cp311-macosx_10_13_x86_64.whl", hash = "sha256:b4c854ef3adc177950a8dfc81a86f5115d2abd545751a304c5bcf2c2c7283cfe", size = 184344, upload-time = "2025-09-08T23:22:26.456Z" },
+    { url = "https://files.pythonhosted.org/packages/4f/8b/f0e4c441227ba756aafbe78f117485b25bb26b1c059d01f137fa6d14896b/cffi-2.0.0-cp311-cp311-macosx_11_0_arm64.whl", hash = "sha256:2de9a304e27f7596cd03d16f1b7c72219bd944e99cc52b84d0145aefb07cbd3c", size = 180560, upload-time = "2025-09-08T23:22:28.197Z" },
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 version = "0.1.0"
@@ -323,6 +482,8 @@ dependencies = [
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     { name = "croniter" },
     { name = "edge-tts" },
+    { name = "google-api-python-client" },
+    { name = "google-auth-oauthlib" },
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     { name = "croniter", specifier = ">=2.0" },
     { name = "edge-tts", specifier = ">=6.1" },
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