Add document export (.docx) and email delivery feature

Press releases now auto-generate .docx files alongside .txt for native
Google Docs import. New email_file chat tool sends files via Gmail SMTP
with app password auth, auto-converting .txt to .docx before sending.
Also includes Press Advantage API config and submit_press_release tool.

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

cheddahbot/config.py

@@ -48,6 +48,22 @@ class ClickUpConfig:
     enabled: bool = False
 
 
+@dataclass
+class PressAdvantageConfig:
+    api_key: str = ""
+    base_url: str = "https://app.pressadvantage.com"
+
+
+@dataclass
+class EmailConfig:
+    smtp_host: str = "smtp.gmail.com"
+    smtp_port: int = 465
+    username: str = ""
+    password: str = ""
+    default_to: str = ""
+    enabled: bool = False
+
+
 @dataclass
 class Config:
     chat_model: str = "openai/gpt-4o-mini"
@@ -61,6 +77,8 @@ class Config:
     scheduler: SchedulerConfig = field(default_factory=SchedulerConfig)
     shell: ShellConfig = field(default_factory=ShellConfig)
     clickup: ClickUpConfig = field(default_factory=ClickUpConfig)
+    press_advantage: PressAdvantageConfig = field(default_factory=PressAdvantageConfig)
+    email: EmailConfig = field(default_factory=EmailConfig)
 
     # Derived paths
     root_dir: Path = field(default_factory=lambda: ROOT_DIR)
@@ -99,6 +117,14 @@ def load_config() -> Config:
             for k, v in data["clickup"].items():
                 if hasattr(cfg.clickup, k):
                     setattr(cfg.clickup, k, v)
+        if "press_advantage" in data and isinstance(data["press_advantage"], dict):
+            for k, v in data["press_advantage"].items():
+                if hasattr(cfg.press_advantage, k):
+                    setattr(cfg.press_advantage, k, v)
+        if "email" in data and isinstance(data["email"], dict):
+            for k, v in data["email"].items():
+                if hasattr(cfg.email, k):
+                    setattr(cfg.email, k, v)
 
     # Env var overrides (CHEDDAH_ prefix)
     cfg.openrouter_api_key = os.getenv("OPENROUTER_API_KEY", "")
@@ -121,6 +147,19 @@ def load_config() -> Config:
     # Auto-enable if token is present
     cfg.clickup.enabled = bool(cfg.clickup.api_token)
 
+    # Press Advantage env var override
+    if key := os.getenv("PRESS_ADVANTAGE_API"):
+        cfg.press_advantage.api_key = key
+
+    # Email env var overrides
+    if gmail_user := os.getenv("GMAIL_USERNAME"):
+        cfg.email.username = gmail_user
+    if gmail_pass := os.getenv("GMAIL_APP_PASSWORD"):
+        cfg.email.password = gmail_pass
+    if default_to := os.getenv("EMAIL_DEFAULT_TO"):
+        cfg.email.default_to = default_to
+    cfg.email.enabled = bool(cfg.email.username and cfg.email.password)
+
     # Ensure data directories exist
     cfg.data_dir.mkdir(parents=True, exist_ok=True)
     (cfg.data_dir / "uploads").mkdir(exist_ok=True)

cheddahbot/docx_export.py

@@ -0,0 +1,77 @@
+"""Convert plain-text press releases to formatted .docx files."""
+
+from __future__ import annotations
+
+import logging
+from pathlib import Path
+
+from docx import Document
+from docx.shared import Pt
+
+log = logging.getLogger(__name__)
+
+# Standard PR format
+_HEADLINE_FONT = "Times New Roman"
+_HEADLINE_SIZE = Pt(16)
+_BODY_FONT = "Times New Roman"
+_BODY_SIZE = Pt(12)
+
+
+def text_to_docx(text: str, output_path: Path) -> Path:
+    """Convert a plain-text press release into a formatted .docx file.
+
+    Layout:
+      - First non-blank line → headline (bold, 16pt Times New Roman)
+      - Remaining lines → body paragraphs (12pt Times New Roman)
+      - Blank lines in the source start new paragraphs.
+
+    Returns the output path.
+    """
+    doc = Document()
+
+    # Set default font for the document
+    style = doc.styles["Normal"]
+    style.font.name = _BODY_FONT
+    style.font.size = _BODY_SIZE
+
+    lines = text.strip().splitlines()
+    if not lines:
+        doc.save(str(output_path))
+        return output_path
+
+    # First non-blank line is the headline
+    headline = lines[0].strip()
+    h_para = doc.add_paragraph()
+    h_run = h_para.add_run(headline)
+    h_run.bold = True
+    h_run.font.name = _HEADLINE_FONT
+    h_run.font.size = _HEADLINE_SIZE
+
+    # Group remaining lines into paragraphs (split on blank lines)
+    body_lines = lines[1:]
+    current_para_lines: list[str] = []
+
+    for line in body_lines:
+        if line.strip() == "":
+            if current_para_lines:
+                _add_body_paragraph(doc, " ".join(current_para_lines))
+                current_para_lines = []
+        else:
+            current_para_lines.append(line.strip())
+
+    # Flush any remaining lines
+    if current_para_lines:
+        _add_body_paragraph(doc, " ".join(current_para_lines))
+
+    output_path.parent.mkdir(parents=True, exist_ok=True)
+    doc.save(str(output_path))
+    log.info("Saved .docx: %s", output_path)
+    return output_path
+
+
+def _add_body_paragraph(doc: Document, text: str) -> None:
+    """Add a body paragraph with standard PR formatting."""
+    para = doc.add_paragraph()
+    run = para.add_run(text)
+    run.font.name = _BODY_FONT
+    run.font.size = _BODY_SIZE

cheddahbot/email.py

@@ -0,0 +1,56 @@
+"""Email client for sending files via Gmail SMTP."""
+
+from __future__ import annotations
+
+import logging
+import smtplib
+from email import encoders
+from email.mime.base import MIMEBase
+from email.mime.multipart import MIMEMultipart
+from email.mime.text import MIMEText
+from pathlib import Path
+
+log = logging.getLogger(__name__)
+
+
+class EmailClient:
+    """Send emails with attachments via SMTP_SSL (Gmail app-password friendly)."""
+
+    def __init__(self, smtp_host: str, smtp_port: int, username: str, password: str):
+        self.smtp_host = smtp_host
+        self.smtp_port = smtp_port
+        self.username = username
+        self.password = password
+
+    def send(
+        self,
+        to: str,
+        subject: str,
+        body: str,
+        attachments: list[Path] | None = None,
+    ) -> None:
+        """Send an email, optionally with file attachments.
+
+        Raises smtplib.SMTPException on failure.
+        """
+        msg = MIMEMultipart()
+        msg["From"] = self.username
+        msg["To"] = to
+        msg["Subject"] = subject
+        msg.attach(MIMEText(body, "plain"))
+
+        for file_path in attachments or []:
+            part = MIMEBase("application", "octet-stream")
+            part.set_payload(file_path.read_bytes())
+            encoders.encode_base64(part)
+            part.add_header(
+                "Content-Disposition",
+                f"attachment; filename={file_path.name}",
+            )
+            msg.attach(part)
+
+        log.info("Sending email to %s — subject: %s", to, subject)
+        with smtplib.SMTP_SSL(self.smtp_host, self.smtp_port) as server:
+            server.login(self.username, self.password)
+            server.send_message(msg)
+        log.info("Email sent successfully to %s", to)

cheddahbot/tools/email_tool.py

@@ -0,0 +1,73 @@
+"""Email delivery tool — send files as attachments via Gmail SMTP."""
+
+from __future__ import annotations
+
+import logging
+from pathlib import Path
+
+from ..docx_export import text_to_docx
+from ..email import EmailClient
+from . import tool
+
+log = logging.getLogger(__name__)
+
+
+@tool(
+    "email_file",
+    description=(
+        "Email a file as an attachment. If the file is .txt it is auto-converted "
+        "to .docx before sending. Defaults to the configured recipient address."
+    ),
+    category="delivery",
+)
+def email_file(
+    file_path: str,
+    to: str = "",
+    subject: str = "",
+    ctx: dict | None = None,
+) -> str:
+    """Send a file by email, auto-converting .txt to .docx."""
+    if not ctx or "config" not in ctx:
+        return "Error: email tool requires agent context."
+
+    email_cfg = ctx["config"].email
+    if not email_cfg.enabled:
+        return "Error: email not configured. Set GMAIL_USERNAME and GMAIL_APP_PASSWORD in .env."
+
+    src = Path(file_path)
+    if not src.exists():
+        return f"Error: file not found: {file_path}"
+
+    # Auto-convert .txt → .docx
+    if src.suffix.lower() == ".txt":
+        docx_path = src.with_suffix(".docx")
+        text_to_docx(src.read_text(encoding="utf-8"), docx_path)
+        attachment = docx_path
+    else:
+        attachment = src
+
+    recipient = to or email_cfg.default_to
+    if not recipient:
+        return "Error: no recipient specified and EMAIL_DEFAULT_TO not set."
+
+    mail_subject = subject or f"CheddahBot: {attachment.stem}"
+
+    client = EmailClient(
+        smtp_host=email_cfg.smtp_host,
+        smtp_port=email_cfg.smtp_port,
+        username=email_cfg.username,
+        password=email_cfg.password,
+    )
+
+    try:
+        client.send(
+            to=recipient,
+            subject=mail_subject,
+            body=f"Attached: {attachment.name}",
+            attachments=[attachment],
+        )
+    except Exception as e:
+        log.error("Email send failed: %s", e)
+        return f"Error sending email: {e}"
+
+    return f"Sent {attachment.name} to {recipient}."

cheddahbot/tools/press_release.py

@@ -17,6 +17,8 @@ import time
 from datetime import datetime
 from pathlib import Path
 
+from ..docx_export import text_to_docx
+from ..press_advantage import PressAdvantageClient
 from . import tool
 
 log = logging.getLogger(__name__)
@@ -370,6 +372,7 @@ def write_press_releases(
     log.info("[PR Pipeline] Step 3/4: Writing 2 press releases...")
     pr_texts: list[str] = []
     pr_files: list[str] = []
+    docx_files: list[str] = []
     for i, headline in enumerate(winners):
         log.info("[PR Pipeline]   Writing PR %d/2: %s", i + 1, headline[:60])
         _set_status(ctx, f"Step 3/4: Writing press release {i+1}/2 — {headline[:60]}...")
@@ -403,6 +406,11 @@ def write_press_releases(
         filepath.write_text(clean_result, encoding="utf-8")
         pr_files.append(str(filepath))
 
+        # Also save as .docx for Google Docs import
+        docx_path = output_dir / f"{slug}_{today}.docx"
+        text_to_docx(clean_result, docx_path)
+        docx_files.append(str(docx_path))
+
     # ── Step 4: Generate 2 JSON-LD schemas (Sonnet + WebSearch) ───────────
     log.info("[PR Pipeline] Step 4/4: Generating 2 JSON-LD schemas...")
     schema_texts: list[str] = []
@@ -455,7 +463,8 @@ def write_press_releases(
         wc = _word_count(pr_texts[i])
         output_parts.append(f"## Press Release {label}: {winners[i]}")
         output_parts.append(f"**Word count:** {wc}")
-        output_parts.append(f"**File:** `{pr_files[i]}`\n")
+        output_parts.append(f"**File:** `{pr_files[i]}`")
+        output_parts.append(f"**Docx:** `{docx_files[i]}`\n")
         output_parts.append(pr_texts[i])
         output_parts.append("\n---\n")
         output_parts.append(f"### Schema {label}")
@@ -474,6 +483,85 @@ def write_press_releases(
     return "\n".join(output_parts)
 
 
+def _parse_company_org_ids(companies_text: str) -> dict[str, int]:
+    """Parse companies.md and return {company_name_lower: pa_org_id}."""
+    mapping: dict[str, int] = {}
+    current_company = ""
+    for line in companies_text.splitlines():
+        line = line.strip()
+        if line.startswith("## "):
+            current_company = line[3:].strip()
+        elif line.startswith("- **PA Org ID:**") and current_company:
+            try:
+                org_id = int(line.split(":**")[1].strip())
+                mapping[current_company.lower()] = org_id
+            except (ValueError, IndexError):
+                pass
+    return mapping
+
+
+def _fuzzy_match_company(name: str, candidates: dict[str, int]) -> int | None:
+    """Try to match a company name against the org ID mapping.
+
+    Tries exact match first, then substring containment in both directions.
+    """
+    name_lower = name.lower().strip()
+
+    # Exact match
+    if name_lower in candidates:
+        return candidates[name_lower]
+
+    # Substring: input contains a known company name, or vice versa
+    for key, org_id in candidates.items():
+        if key in name_lower or name_lower in key:
+            return org_id
+
+    return None
+
+
+def _text_to_html(text: str, links: list[dict] | None = None) -> str:
+    """Convert plain text to HTML with link injection.
+
+    Args:
+        text: Plain text press release body.
+        links: List of dicts with 'url' and 'anchor' keys. Each anchor's first
+               occurrence in the text is wrapped in an <a> tag.
+
+    Returns:
+        HTML string with <p> tags and injected links.
+    """
+    # Inject anchor text links before paragraph splitting
+    if links:
+        for link in links:
+            anchor = link.get("anchor", "")
+            url = link.get("url", "")
+            if anchor and url:
+                # Replace first occurrence only
+                html_link = f'<a href="{url}">{anchor}</a>'
+                text = text.replace(anchor, html_link, 1)
+
+    # Split into paragraphs on double newlines
+    paragraphs = re.split(r"\n\s*\n", text.strip())
+
+    html_parts = []
+    for para in paragraphs:
+        # Collapse internal newlines to spaces within a paragraph
+        para = re.sub(r"\s*\n\s*", " ", para).strip()
+        if not para:
+            continue
+
+        # Convert bare URLs to links (skip already-linked ones)
+        para = re.sub(
+            r'(?<!href=")(?<!">)(https?://\S+)',
+            r'<a href="\1">\1</a>',
+            para,
+        )
+
+        html_parts.append(f"<p>{para}</p>")
+
+    return "\n".join(html_parts)
+
+
 def _extract_json(text: str) -> str | None:
     """Try to pull a JSON object out of LLM output (strip fences, prose, etc)."""
     stripped = text.strip()
@@ -505,4 +593,143 @@ def _extract_json(text: str) -> str | None:
         except json.JSONDecodeError:
             pass
 
-    return None
+    return None  # noqa: RET501
+
+
+# ---------------------------------------------------------------------------
+# Submit tool
+# ---------------------------------------------------------------------------
+
+@tool(
+    "submit_press_release",
+    description=(
+        "Submit a press release to Press Advantage as a draft. Takes the PR text "
+        "(or file path), headline, company name, and links to inject. Converts to "
+        "HTML, resolves the PA organization ID, and creates a draft release for "
+        "review. The release will NOT auto-publish — Bryan must review and approve "
+        "it in the PA dashboard."
+    ),
+    category="content",
+)
+def submit_press_release(
+    headline: str,
+    company_name: str,
+    links: str = "",
+    pr_text: str = "",
+    file_path: str = "",
+    description: str = "",
+    ctx: dict = None,
+) -> str:
+    """Submit a finished press release to Press Advantage as a draft."""
+    # --- Get config ---
+    if not ctx or "config" not in ctx:
+        return "Error: submit_press_release requires agent context."
+
+    config = ctx["config"]
+    api_key = config.press_advantage.api_key
+    if not api_key:
+        return (
+            "Error: PRESS_ADVANTAGE_API key not configured. "
+            "Set the PRESS_ADVANTAGE_API environment variable in .env."
+        )
+
+    # --- Get PR text ---
+    if not pr_text and file_path:
+        path = Path(file_path)
+        if not path.exists():
+            return f"Error: file not found: {file_path}"
+        pr_text = path.read_text(encoding="utf-8")
+
+    if not pr_text:
+        return "Error: provide either pr_text or file_path with the press release content."
+
+    # --- Validate word count ---
+    wc = _word_count(pr_text)
+    if wc < 550:
+        return (
+            f"Error: press release is only {wc} words. "
+            f"Press Advantage requires at least 550 words. Please expand the content."
+        )
+
+    # --- Parse links ---
+    link_list: list[dict] = []
+    if links:
+        try:
+            link_list = json.loads(links)
+        except json.JSONDecodeError:
+            return "Error: 'links' must be a valid JSON array, e.g. '[{\"url\": \"...\", \"anchor\": \"...\"}]'"
+
+    # --- Convert to HTML ---
+    html_body = _text_to_html(pr_text, link_list)
+
+    # --- Look up PA org ID ---
+    companies_text = _load_file_if_exists(_COMPANIES_FILE)
+    org_mapping = _parse_company_org_ids(companies_text)
+    org_id = _fuzzy_match_company(company_name, org_mapping)
+
+    # Fallback: try live API lookup
+    if org_id is None:
+        log.info("Org ID not found in companies.md for '%s', trying live API...", company_name)
+        try:
+            client = PressAdvantageClient(api_key)
+            try:
+                orgs = client.get_organizations()
+                # Build a mapping from API results and try fuzzy match
+                api_mapping: dict[str, int] = {}
+                for org in orgs:
+                    org_name = org.get("name", "")
+                    oid = org.get("id")
+                    if org_name and oid:
+                        api_mapping[org_name.lower()] = int(oid)
+                org_id = _fuzzy_match_company(company_name, api_mapping)
+            finally:
+                client.close()
+        except Exception as e:
+            log.warning("Failed to fetch orgs from PA API: %s", e)
+
+    if org_id is None:
+        return (
+            f"Error: could not find Press Advantage organization for '{company_name}'. "
+            f"Add a 'PA Org ID' entry to skills/companies.md or check the company name."
+        )
+
+    # --- Auto-generate description if not provided ---
+    if not description:
+        # Extract a keyword from the headline (drop the company name, take remaining key phrase)
+        keyword = headline
+        for part in [company_name, "Inc.", "LLC", "Corp.", "Ltd.", "Limited", "Inc"]:
+            keyword = keyword.replace(part, "").strip()
+        # Clean up and take first meaningful chunk
+        keyword = re.sub(r"\s+", " ", keyword).strip(" -\u2013\u2014,")
+        description = f"{company_name} - {keyword}" if keyword else company_name
+
+    # --- Submit to PA ---
+    log.info("Submitting PR to Press Advantage: org=%d, title='%s'", org_id, headline[:60])
+    client = PressAdvantageClient(api_key)
+    try:
+        result = client.create_release(
+            org_id=org_id,
+            title=headline,
+            body=html_body,
+            description=description,
+            distribution="standard",
+            schedule_distribution="false",
+        )
+    except Exception as e:
+        return f"Error submitting to Press Advantage: {e}"
+    finally:
+        client.close()
+
+    # --- Format response ---
+    release_id = result.get("id", "unknown")
+    status = result.get("state", result.get("status", "draft"))
+    return (
+        f"Press release submitted to Press Advantage as a DRAFT.\n\n"
+        f"- **Release ID:** {release_id}\n"
+        f"- **Status:** {status}\n"
+        f"- **Organization:** {company_name} (ID: {org_id})\n"
+        f"- **Title:** {headline}\n"
+        f"- **Word count:** {wc}\n"
+        f"- **Links injected:** {len(link_list)}\n\n"
+        f"**Next step:** Review and approve in the Press Advantage dashboard before publishing."
+    )

config.yaml

@@ -34,6 +34,11 @@ shell:
     - ":(){:|:&};:"
   require_approval: false        # If true, shell commands need user confirmation
 
+# Email delivery (credentials in .env, not here)
+email:
+  smtp_host: "smtp.gmail.com"
+  smtp_port: 465
+
 # ClickUp integration
 clickup:
   poll_interval_minutes: 20       # 3x per hour

pyproject.toml

@@ -14,6 +14,7 @@ dependencies = [
     "beautifulsoup4>=4.12",
     "croniter>=2.0",
     "edge-tts>=6.1",
+    "python-docx>=1.2.0",
 ]
 
 [build-system]

tests/test_docx_export.py

@@ -0,0 +1,74 @@
+"""Tests for the .docx export module."""
+
+from __future__ import annotations
+
+from pathlib import Path
+
+from docx import Document
+
+from cheddahbot.docx_export import text_to_docx
+
+SAMPLE_PR = (
+    "Acme Corp Expands Digital Marketing Services Nationwide\n"
+    "\n"
+    "NEW YORK, Feb 16, 2026 -- Acme Corp, a leader in digital marketing\n"
+    "solutions, today announced the expansion of its services to all 50 states.\n"
+    "\n"
+    "The company has been operating in the Northeast for the past decade and is\n"
+    "now bringing its full suite of SEO, content marketing, and paid advertising\n"
+    "services to clients across the country.\n"
+    "\n"
+    '"We are thrilled to bring our proven approach to businesses nationwide,"\n'
+    "said Jane Smith, CEO of Acme Corp.\n"
+    "\n"
+    "For more information, visit www.acmecorp.com.\n"
+)
+
+
+def test_text_to_docx_creates_file(tmp_path: Path):
+    """Verify .docx file is created at the expected path."""
+    out = tmp_path / "test.docx"
+    result = text_to_docx(SAMPLE_PR, out)
+
+    assert result == out
+    assert out.exists()
+    assert out.stat().st_size > 0
+
+
+def test_text_to_docx_headline_is_bold(tmp_path: Path):
+    """First paragraph should be the headline with bold formatting."""
+    out = tmp_path / "test.docx"
+    text_to_docx(SAMPLE_PR, out)
+
+    doc = Document(str(out))
+    headline_para = doc.paragraphs[0]
+    assert headline_para.runs[0].bold is True
+    assert "Acme Corp Expands" in headline_para.text
+
+
+def test_text_to_docx_body_paragraphs(tmp_path: Path):
+    """Body text should be split into multiple paragraphs."""
+    out = tmp_path / "test.docx"
+    text_to_docx(SAMPLE_PR, out)
+
+    doc = Document(str(out))
+    # Headline + 4 body paragraphs
+    assert len(doc.paragraphs) >= 4
+
+
+def test_text_to_docx_empty_text(tmp_path: Path):
+    """Empty input should still produce a valid .docx."""
+    out = tmp_path / "empty.docx"
+    text_to_docx("", out)
+
+    assert out.exists()
+    doc = Document(str(out))
+    assert len(doc.paragraphs) == 0
+
+
+def test_text_to_docx_creates_parent_dirs(tmp_path: Path):
+    """Should create parent directories if they don't exist."""
+    out = tmp_path / "sub" / "dir" / "test.docx"
+    text_to_docx(SAMPLE_PR, out)
+
+    assert out.exists()

tests/test_email.py

@@ -0,0 +1,82 @@
+"""Tests for the email client (mocked SMTP)."""
+
+from __future__ import annotations
+
+from pathlib import Path
+from unittest.mock import MagicMock, patch
+
+from cheddahbot.email import EmailClient
+
+
+@patch("cheddahbot.email.smtplib.SMTP_SSL")
+def test_send_plain_email(mock_smtp_cls):
+    """Send a simple email without attachments."""
+    mock_server = MagicMock()
+    mock_smtp_cls.return_value.__enter__ = MagicMock(return_value=mock_server)
+    mock_smtp_cls.return_value.__exit__ = MagicMock(return_value=False)
+
+    client = EmailClient("smtp.gmail.com", 465, "bot@test.com", "secret")
+    client.send(to="user@corp.com", subject="Test", body="Hello")
+
+    mock_smtp_cls.assert_called_once_with("smtp.gmail.com", 465)
+    mock_server.login.assert_called_once_with("bot@test.com", "secret")
+    mock_server.send_message.assert_called_once()
+
+    # Verify the message contents
+    sent_msg = mock_server.send_message.call_args[0][0]
+    assert sent_msg["To"] == "user@corp.com"
+    assert sent_msg["Subject"] == "Test"
+    assert sent_msg["From"] == "bot@test.com"
+
+
+@patch("cheddahbot.email.smtplib.SMTP_SSL")
+def test_send_with_attachment(mock_smtp_cls, tmp_path: Path):
+    """Send an email with a file attachment."""
+    mock_server = MagicMock()
+    mock_smtp_cls.return_value.__enter__ = MagicMock(return_value=mock_server)
+    mock_smtp_cls.return_value.__exit__ = MagicMock(return_value=False)
+
+    # Create a test file
+    test_file = tmp_path / "report.docx"
+    test_file.write_bytes(b"fake docx content")
+
+    client = EmailClient("smtp.gmail.com", 465, "bot@test.com", "secret")
+    client.send(
+        to="user@corp.com",
+        subject="Report",
+        body="See attached",
+        attachments=[test_file],
+    )
+
+    mock_server.send_message.assert_called_once()
+    sent_msg = mock_server.send_message.call_args[0][0]
+
+    # Should have 2 parts: body text + 1 attachment
+    payloads = sent_msg.get_payload()
+    assert len(payloads) == 2
+    assert payloads[1].get_filename() == "report.docx"
+
+
+@patch("cheddahbot.email.smtplib.SMTP_SSL")
+def test_send_with_multiple_attachments(mock_smtp_cls, tmp_path: Path):
+    """Send an email with multiple attachments."""
+    mock_server = MagicMock()
+    mock_smtp_cls.return_value.__enter__ = MagicMock(return_value=mock_server)
+    mock_smtp_cls.return_value.__exit__ = MagicMock(return_value=False)
+
+    file_a = tmp_path / "a.docx"
+    file_b = tmp_path / "b.docx"
+    file_a.write_bytes(b"content a")
+    file_b.write_bytes(b"content b")
+
+    client = EmailClient("smtp.gmail.com", 465, "bot@test.com", "secret")
+    client.send(
+        to="user@corp.com",
+        subject="Two files",
+        body="Both attached",
+        attachments=[file_a, file_b],
+    )
+
+    sent_msg = mock_server.send_message.call_args[0][0]
+    payloads = sent_msg.get_payload()
+    assert len(payloads) == 3  # body + 2 attachments

uv.lock

@@ -327,6 +327,7 @@ dependencies = [
     { name = "httpx" },
     { name = "numpy" },
     { name = "openai" },
+    { name = "python-docx" },
     { name = "python-dotenv" },
     { name = "pyyaml" },
     { name = "sentence-transformers" },
@@ -357,6 +358,7 @@ requires-dist = [
     { name = "httpx", specifier = ">=0.27" },
     { name = "numpy", specifier = ">=1.24" },
     { name = "openai", specifier = ">=1.30" },
+    { name = "python-docx", specifier = ">=1.2.0" },
     { name = "python-dotenv", specifier = ">=1.0" },
     { name = "pyyaml", specifier = ">=6.0" },
     { name = "sentence-transformers", specifier = ">=3.0" },
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 ]
 
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