diff --git a/.github/workflows/generate-agendas.yml b/.github/workflows/generate-agendas.yml
new file mode 100644
index 0000000..fed6df3
--- /dev/null
+++ b/.github/workflows/generate-agendas.yml
@@ -0,0 +1,50 @@
+name: Generate Meeting Agendas
+
+on:
+  schedule:
+    - cron: "0 0 1 * *"
+  workflow_dispatch:
+
+permissions:
+  contents: write
+
+jobs:
+  generate-agendas:
+    runs-on: ubuntu-latest
+
+    steps:
+      - name: Checkout repository
+        uses: actions/checkout@v4
+
+      - name: Install uv
+        uses: astral-sh/setup-uv@v4
+
+      - name: Install dependencies
+        run: uv sync
+
+      - name: Write service account JSON to temp file
+        run: echo '${{ secrets.GOOGLE_SERVICE_ACCOUNT_JSON }}' > /tmp/service_account.json
+
+      - name: Run agenda generator
+        env:
+          GOOGLE_SERVICE_ACCOUNT_JSON: /tmp/service_account.json
+          GOOGLE_CALENDAR_ID: ${{ secrets.GOOGLE_CALENDAR_ID }}
+          TELEGRAM_BOT_TOKEN: ${{ secrets.TELEGRAM_BOT_TOKEN }}
+          TELEGRAM_CHAT_ID: ${{ secrets.TELEGRAM_CHAT_ID }}
+        run: uv run agenda_generator.py
+
+      - name: Clean up service account file
+        if: always()
+        run: rm -f /tmp/service_account.json
+
+      - name: Check for changes and commit
+        run: |
+          if [ -n "$(git status --porcelain)" ]; then
+            git config user.name "github-actions[bot]"
+            git config user.email "github-actions[bot]@users.noreply.github.com"
+            git add .
+            git commit -m "Generate meeting agendas for $(date +'%B %Y')"
+            git push origin main
+          else
+            echo "No new agenda files generated. Skipping commit."
+          fi
diff --git a/.gitignore b/.gitignore
index 5b6f6f6..2094ecc 100644
--- a/.gitignore
+++ b/.gitignore
@@ -2,3 +2,5 @@
 *swp
 *~
 .DS_Store
+__pycache__
+.kiro/
\ No newline at end of file
diff --git a/agenda_generator.py b/agenda_generator.py
new file mode 100644
index 0000000..5b43b17
--- /dev/null
+++ b/agenda_generator.py
@@ -0,0 +1,434 @@
+"""Automated meeting agenda generation for Pawprint Prototyping."""
+
+from __future__ import annotations
+
+import calendar
+import datetime
+import glob
+import logging
+import os
+import sys
+from dataclasses import dataclass
+
+import frontmatter
+import jinja2
+import requests
+from google.oauth2 import service_account
+from googleapiclient.discovery import build
+
+logger = logging.getLogger(__name__)
+
+
+@dataclass
+class TemplateConfig:
+    """Parsed from YAML front matter with defaults applied."""
+
+    event_name: str  # Google Calendar event name to match
+    output_dir: str  # e.g., "board/agendas"
+    meeting_type: str  # e.g., "Board Meeting"
+    telegram_notify: bool  # default: True
+    telegram_chat_id: str | None  # override default chat ID, default: None
+    template_content: str  # Jinja2 template body (after front matter)
+    template_path: str  # path to the template file (for logging)
+
+
+DEFAULTS = {
+    "event_name": "",  # required — empty triggers skip
+    "output_dir": "",  # required — empty triggers skip
+    "meeting_type": "Meeting",
+    "telegram_notify": True,
+    "telegram_chat_id": None,
+}
+
+
+@dataclass
+class CalendarEvent:
+    """A Google Calendar event with summary and date."""
+
+    summary: str  # event name/title
+    date: datetime.date  # event date
+
+
+def ordinal(n: int) -> str:
+    """Return English ordinal string for a day number.
+
+    Examples: 1 -> '1st', 2 -> '2nd', 3 -> '3rd', 11 -> '11th', 21 -> '21st'
+    """
+    if 11 <= (n % 100) <= 13:
+        suffix = "th"
+    elif n % 10 == 1:
+        suffix = "st"
+    elif n % 10 == 2:
+        suffix = "nd"
+    elif n % 10 == 3:
+        suffix = "rd"
+    else:
+        suffix = "th"
+    return f"{n}{suffix}"
+
+
+def build_agenda_path(output_dir: str, date: datetime.date) -> str:
+    """Construct the full agenda file path.
+
+    Returns: {output_dir}/{year}/agenda_{YYYY-MM-DD}.md
+    """
+    return os.path.join(output_dir, str(date.year), f"agenda_{date.isoformat()}.md")
+
+
+def agenda_file_exists(output_dir: str, date: datetime.date) -> bool:
+    """Check if an agenda file already exists for the given date."""
+    return os.path.exists(build_agenda_path(output_dir, date))
+
+
+def discover_templates(templates_dir: str) -> list[TemplateConfig]:
+    """Scan templates_dir for *.j2 files and parse YAML front matter.
+
+    Returns list of TemplateConfig with merged defaults.
+    Skips templates with invalid front matter (logs error).
+    Skips templates missing required keys event_name or output_dir (logs warning).
+    """
+    templates: list[TemplateConfig] = []
+    pattern = os.path.join(templates_dir, "*.j2")
+
+    for filepath in sorted(glob.glob(pattern)):
+        try:
+            post = frontmatter.load(filepath)
+        except Exception as e:
+            logger.error("Failed to parse front matter in %s: %s", filepath, e)
+            continue
+
+        metadata = dict(post.metadata)
+        merged = {**DEFAULTS, **metadata}
+
+        if not merged["event_name"] or not merged["output_dir"]:
+            logger.warning(
+                "Skipping %s: missing required key event_name or output_dir",
+                filepath,
+            )
+            continue
+
+        config = TemplateConfig(
+            event_name=merged["event_name"],
+            output_dir=merged["output_dir"],
+            meeting_type=merged["meeting_type"],
+            telegram_notify=merged["telegram_notify"],
+            telegram_chat_id=merged["telegram_chat_id"],
+            template_content=post.content,
+            template_path=filepath,
+        )
+        templates.append(config)
+
+    return templates
+
+
+def compute_month_bounds(year: int, month: int) -> tuple[str, str]:
+    """Compute timeMin and timeMax spanning exactly the target month in UTC.
+
+    Returns (timeMin, timeMax) as ISO 8601 strings with Z suffix.
+    timeMin = first day of month at 00:00:00 UTC
+    timeMax = first day of next month at 00:00:00 UTC
+    """
+    time_min = f"{year:04d}-{month:02d}-01T00:00:00Z"
+
+    if month == 12:
+        next_year = year + 1
+        next_month = 1
+    else:
+        next_year = year
+        next_month = month + 1
+
+    time_max = f"{next_year:04d}-{next_month:02d}-01T00:00:00Z"
+    return time_min, time_max
+
+
+def get_events_in_month(
+    calendar_id: str,
+    credentials_path: str,
+    year: int,
+    month: int,
+) -> list[CalendarEvent]:
+    """Query Google Calendar API for all events in the given month.
+
+    Authenticates via service account credentials file.
+    Returns list of CalendarEvent(summary, date).
+    On auth/API errors: logs error and exits with non-zero status.
+    """
+    SCOPES = ["https://www.googleapis.com/auth/calendar.readonly"]
+
+    try:
+        credentials = service_account.Credentials.from_service_account_file(
+            credentials_path, scopes=SCOPES
+        )
+    except Exception as e:
+        logger.error("Failed to authenticate with Google Calendar API: %s", e)
+        sys.exit(1)
+
+    try:
+        service = build("calendar", "v3", credentials=credentials)
+    except Exception as e:
+        logger.error("Failed to build Google Calendar service: %s", e)
+        sys.exit(1)
+
+    time_min, time_max = compute_month_bounds(year, month)
+
+    try:
+        events_result = (
+            service.events()
+            .list(
+                calendarId=calendar_id,
+                timeMin=time_min,
+                timeMax=time_max,
+                singleEvents=True,
+            )
+            .execute()
+        )
+    except Exception as e:
+        logger.error("Failed to fetch events from Google Calendar API: %s", e)
+        sys.exit(1)
+
+    events: list[CalendarEvent] = []
+    for item in events_result.get("items", []):
+        summary = item.get("summary", "")
+        # Extract date from either 'date' (all-day) or 'dateTime' field
+        start = item.get("start", {})
+        date_str = start.get("date") or start.get("dateTime", "")
+        if date_str:
+            # Parse date portion (first 10 chars for YYYY-MM-DD)
+            event_date = datetime.date.fromisoformat(date_str[:10])
+        else:
+            continue
+        events.append(CalendarEvent(summary=summary, date=event_date))
+
+    return events
+
+
+def find_matching_event(
+    events: list[CalendarEvent],
+    event_name: str,
+) -> CalendarEvent | None:
+    """Find first event whose summary matches event_name.
+
+    Returns None if no match.
+    """
+    for event in events:
+        if event.summary == event_name:
+            return event
+    return None
+
+
+def build_template_context(
+    date: datetime.date,
+    meeting_type: str,
+    next_meeting_date: datetime.date | None = None,
+) -> dict:
+    """Build the context dict for Jinja2 template rendering.
+
+    Returns a dict with keys: year, month, day, month_name, day_ordinal,
+    day_plain, date_iso, meeting_type, and next_meeting_* keys if available.
+    """
+    ctx = {
+        "year": date.year,
+        "month": date.month,
+        "day": date.day,
+        "month_name": calendar.month_name[date.month],
+        "day_ordinal": ordinal(date.day),
+        "day_plain": str(date.day),
+        "date_iso": date.isoformat(),
+        "meeting_type": meeting_type,
+        "next_meeting_date": next_meeting_date,
+    }
+    if next_meeting_date is not None:
+        ctx["next_meeting_month_name"] = calendar.month_name[next_meeting_date.month]
+        ctx["next_meeting_day_ordinal"] = ordinal(next_meeting_date.day)
+        ctx["next_meeting_day_plain"] = str(next_meeting_date.day)
+        ctx["next_meeting_weekday"] = calendar.day_name[next_meeting_date.weekday()]
+    else:
+        ctx["next_meeting_month_name"] = ""
+        ctx["next_meeting_day_ordinal"] = ""
+        ctx["next_meeting_day_plain"] = ""
+        ctx["next_meeting_weekday"] = ""
+    return ctx
+
+
+def write_agenda(path: str, content: str) -> None:
+    """Create parent directories if needed and write content to path."""
+    os.makedirs(os.path.dirname(path), exist_ok=True)
+    with open(path, "w") as f:
+        f.write(content)
+
+
+def render_template(
+    template_content: str,
+    date: datetime.date,
+    meeting_type: str,
+    next_meeting_date: datetime.date | None = None,
+) -> str | None:
+    """Render a Jinja2 template string with date context variables.
+
+    Returns rendered markdown string, or None on Jinja2 rendering errors.
+    """
+    context = build_template_context(date, meeting_type, next_meeting_date)
+    try:
+        template = jinja2.Template(template_content)
+        return template.render(context)
+    except jinja2.TemplateError as e:
+        logger.error("Jinja2 rendering error: %s", e)
+        return None
+
+
+def build_notification_message(meeting_type: str, meeting_date: datetime.date) -> str:
+    """Build a human-readable notification message for Telegram.
+
+    Includes the meeting type and a formatted date (e.g., "January 26, 2026").
+    """
+    formatted_date = meeting_date.strftime("%B %d, %Y").replace(" 0", " ")
+    return f"📋 {meeting_type} agenda has been generated for {formatted_date}."
+
+
+def send_telegram_notification(
+    bot_token: str,
+    chat_id: str,
+    meeting_type: str,
+    meeting_date: datetime.date,
+) -> bool:
+    """Send a Telegram notification about a newly generated agenda.
+
+    POSTs to https://api.telegram.org/bot{token}/sendMessage.
+    Returns True on success, False on failure (logs error, does not raise).
+    """
+    message = build_notification_message(meeting_type, meeting_date)
+    url = f"https://api.telegram.org/bot{bot_token}/sendMessage"
+
+    try:
+        response = requests.post(url, json={"chat_id": chat_id, "text": message})
+        if response.status_code == 200:
+            return True
+        logger.error(
+            "Telegram API returned status %d: %s",
+            response.status_code,
+            response.text,
+        )
+        return False
+    except Exception as e:
+        logger.error("Failed to send Telegram notification: %s", e)
+        return False
+
+
+def main() -> None:
+    """Main orchestrator for agenda generation.
+
+    1. Read env vars for credentials and config
+    2. Discover templates
+    3. Fetch calendar events for current month
+    4. For each template: find matching event, check idempotency,
+       render and write agenda, send notification if configured
+    5. Exit with summary log
+    """
+    logging.basicConfig(level=logging.INFO)
+
+    # Read required environment variables
+    credentials_path = os.environ.get("GOOGLE_SERVICE_ACCOUNT_JSON")
+    calendar_id = os.environ.get("GOOGLE_CALENDAR_ID")
+
+    if not credentials_path or not calendar_id:
+        logger.error(
+            "Missing required environment variables: "
+            "GOOGLE_SERVICE_ACCOUNT_JSON and GOOGLE_CALENDAR_ID must be set."
+        )
+        sys.exit(1)
+
+    # Read optional environment variables for Telegram
+    bot_token = os.environ.get("TELEGRAM_BOT_TOKEN")
+    default_chat_id = os.environ.get("TELEGRAM_CHAT_ID")
+    telegram_enabled = True
+
+    if not bot_token or not default_chat_id:
+        logger.warning(
+            "Telegram environment variables (TELEGRAM_BOT_TOKEN, TELEGRAM_CHAT_ID) "
+            "not fully configured. Telegram notifications disabled."
+        )
+        telegram_enabled = False
+
+    # Discover templates
+    templates = discover_templates("templates")
+    if not templates:
+        logger.info("No templates found. Nothing to do.")
+        return
+
+    # Get current date and fetch calendar events for this month
+    today = datetime.date.today()
+    year = today.year
+    month = today.month
+
+    events = get_events_in_month(calendar_id, credentials_path, year, month)
+    if not events:
+        logger.info("No events found for %04d-%02d. Nothing to do.", year, month)
+        return
+
+    # Fetch next month's events for next meeting date lookup
+    if month == 12:
+        next_year, next_month = year + 1, 1
+    else:
+        next_year, next_month = year, month + 1
+    next_month_events = get_events_in_month(
+        calendar_id, credentials_path, next_year, next_month
+    )
+
+    # Process each template
+    generated_count = 0
+
+    for config in templates:
+        # Find matching event
+        event = find_matching_event(events, config.event_name)
+        if event is None:
+            logger.warning(
+                "No matching event '%s' found for template %s. Skipping.",
+                config.event_name,
+                config.template_path,
+            )
+            continue
+
+        # Check idempotency
+        if agenda_file_exists(config.output_dir, event.date):
+            logger.info(
+                "Agenda already exists for %s on %s. Skipping.",
+                config.meeting_type,
+                event.date.isoformat(),
+            )
+            continue
+
+        # Look up next meeting date from next month's events
+        next_event = find_matching_event(next_month_events, config.event_name)
+        next_meeting_date = next_event.date if next_event else None
+        if next_meeting_date is None:
+            logger.info(
+                "No next month event found for '%s'. Next meeting date will be empty.",
+                config.event_name,
+            )
+
+        # Render template
+        rendered = render_template(
+            config.template_content, event.date, config.meeting_type, next_meeting_date
+        )
+        if rendered is None:
+            continue
+
+        # Write agenda file
+        agenda_path = build_agenda_path(config.output_dir, event.date)
+        write_agenda(agenda_path, rendered)
+        generated_count += 1
+        logger.info(
+            "Generated agenda: %s (%s)", agenda_path, config.meeting_type
+        )
+
+        # Send Telegram notification if configured
+        if telegram_enabled and config.telegram_notify:
+            chat_id = config.telegram_chat_id or default_chat_id
+            send_telegram_notification(bot_token, chat_id, config.meeting_type, event.date)
+
+    # Log summary
+    logger.info("Agenda generation complete. %d agenda(s) generated.", generated_count)
+
+
+if __name__ == "__main__":
+    main()
diff --git a/pyproject.toml b/pyproject.toml
new file mode 100644
index 0000000..f1966a7
--- /dev/null
+++ b/pyproject.toml
@@ -0,0 +1,18 @@
+[project]
+name = "agenda-generator"
+version = "0.1.0"
+description = "Automated meeting agenda generation for Pawprint Prototyping"
+requires-python = ">=3.11"
+dependencies = [
+    "google-api-python-client",
+    "google-auth",
+    "Jinja2",
+    "python-frontmatter",
+    "requests",
+]
+
+[dependency-groups]
+dev = [
+    "pytest",
+    "hypothesis",
+]
diff --git a/templates/board_meeting.j2 b/templates/board_meeting.j2
new file mode 100644
index 0000000..baee3bd
--- /dev/null
+++ b/templates/board_meeting.j2
@@ -0,0 +1,26 @@
+---
+event_name: "Board Meeting"
+output_dir: "board/agendas"
+meeting_type: "Board Meeting"
+---
+# Board Meeting Agenda {{ month_name }} {{ day_plain }}, {{ year }}
+
+## Attendees
+
+### Space Management
+
+#### Tech
+
+#### Finances
+
+### Events
+
+### Corporate Filings
+
+### Motions and Voting
+
+## Next Meeting Date
+{% if next_meeting_date %}- {{ next_meeting_weekday }}, 19:00, {{ next_meeting_month_name }} {{ next_meeting_day_ordinal }}.{% endif %}
+
+## Sidebars
+
diff --git a/templates/general_meeting.j2 b/templates/general_meeting.j2
new file mode 100644
index 0000000..852f41f
--- /dev/null
+++ b/templates/general_meeting.j2
@@ -0,0 +1,33 @@
+---
+event_name: "General Body Meeting"
+output_dir: "general/agendas"
+meeting_type: "General Body Meeting"
+---
+# General Body Meeting Agenda for {{ month_name }} {{ day_ordinal }}, {{ year }}
+
+# Roll Call
+**In Person:**
+
+**Online:**
+
+**Guests:**
+
+# General News
+
+## Tech Updates
+
+# Meetings, events and Interest Groups
+
+# Treasurer Update
+
+# Motions and Voting
+
+# Reminders
+
+# Pupporri
+
+# Next meeting date
+{% if next_meeting_date %}- Next General Meeting {{ next_meeting_weekday }}, {{ next_meeting_month_name }} {{ next_meeting_day_ordinal }}. 7:00pm{% endif %}
+
+# How to join!
+- We depend on your support! $100 a month; talk to the people in blue labcoats to inquire.
diff --git a/test_agenda_generator.py b/test_agenda_generator.py
new file mode 100644
index 0000000..5923cb6
--- /dev/null
+++ b/test_agenda_generator.py
@@ -0,0 +1,684 @@
+"""Property-based tests for agenda_generator.py using Hypothesis."""
+
+import calendar
+import datetime
+import os
+import re
+import tempfile
+
+from hypothesis import given, settings
+from hypothesis import strategies as st
+
+import frontmatter as fm
+
+from agenda_generator import (
+    DEFAULTS,
+    CalendarEvent,
+    TemplateConfig,
+    build_agenda_path,
+    build_notification_message,
+    build_template_context,
+    compute_month_bounds,
+    discover_templates,
+    find_matching_event,
+    ordinal,
+    render_template,
+)
+
+
+# Feature: auto-agenda-generation, Property 5: Ordinal suffix correctness
+@settings(max_examples=100)
+@given(day=st.integers(min_value=1, max_value=31))
+def test_ordinal_suffix_correctness(day: int):
+    """For any day 1-31, ordinal returns the correct English ordinal suffix.
+
+    Validates: Requirements 6.2
+    """
+    result = ordinal(day)
+
+    # Must start with the day number
+    assert result.startswith(str(day))
+
+    # Extract suffix
+    suffix = result[len(str(day)):]
+
+    # Determine expected suffix
+    if 11 <= (day % 100) <= 13:
+        expected_suffix = "th"
+    elif day % 10 == 1:
+        expected_suffix = "st"
+    elif day % 10 == 2:
+        expected_suffix = "nd"
+    elif day % 10 == 3:
+        expected_suffix = "rd"
+    else:
+        expected_suffix = "th"
+
+    assert suffix == expected_suffix, (
+        f"ordinal({day}) = {result!r}, expected suffix {expected_suffix!r} but got {suffix!r}"
+    )
+
+
+# Feature: auto-agenda-generation, Property 3: Agenda path construction follows pattern
+@settings(max_examples=100)
+@given(
+    output_dir=st.text(
+        alphabet=st.characters(whitelist_categories=("L", "N", "P"), blacklist_characters="\x00/\\"),
+        min_size=1,
+        max_size=50,
+    ),
+    date=st.dates(
+        min_value=datetime.date(2000, 1, 1),
+        max_value=datetime.date(2100, 12, 31),
+    ),
+)
+def test_agenda_path_construction_follows_pattern(output_dir: str, date: datetime.date):
+    """For any non-empty output_dir and valid date, build_agenda_path returns
+    a path matching {output_dir}/{year}/agenda_{YYYY-MM-DD}.md with proper zero-padding.
+
+    Validates: Requirements 3.3, 5.4, 6.4
+    """
+    result = build_agenda_path(output_dir, date)
+
+    # Verify year is present as a directory component
+    year_str = str(date.year)
+    month_str = f"{date.month:02d}"
+    day_str = f"{date.day:02d}"
+    expected_filename = f"agenda_{date.year}-{month_str}-{day_str}.md"
+
+    # The path should end with {year}/agenda_{YYYY-MM-DD}.md
+    assert result.endswith(f"{year_str}/{expected_filename}"), (
+        f"Expected path to end with '{year_str}/{expected_filename}', got {result!r}"
+    )
+
+    # The path should start with the output_dir
+    assert result.startswith(output_dir), (
+        f"Expected path to start with {output_dir!r}, got {result!r}"
+    )
+
+    # Verify the full pattern matches {output_dir}/{year}/agenda_{YYYY-MM-DD}.md
+    # Use regex to validate the date portion is zero-padded
+    pattern = re.escape(output_dir) + r"[\\/]" + re.escape(year_str) + r"[\\/]agenda_\d{4}-\d{2}-\d{2}\.md$"
+    assert re.match(pattern, result), (
+        f"Path {result!r} does not match expected pattern"
+    )
+
+    # Verify month and day are zero-padded correctly
+    assert f"-{month_str}-" in result, f"Month not zero-padded in {result!r}"
+    assert result.endswith(f"-{day_str}.md"), f"Day not zero-padded in {result!r}"
+
+
+# Feature: auto-agenda-generation, Property 4: Front matter parsing with defaults merge
+@settings(max_examples=100)
+@given(
+    keys_present=st.sets(
+        st.sampled_from(["event_name", "output_dir", "meeting_type", "telegram_notify", "telegram_chat_id"])
+    ),
+    event_name=st.text(
+        alphabet=st.characters(whitelist_categories=("L", "N", "Pd"), blacklist_characters="\x00"),
+        min_size=1,
+        max_size=30,
+    ),
+    output_dir=st.text(
+        alphabet=st.characters(whitelist_categories=("L", "N", "Pd"), blacklist_characters="\x00"),
+        min_size=1,
+        max_size=30,
+    ),
+    meeting_type=st.text(
+        alphabet=st.characters(whitelist_categories=("L", "N", "Zs"), blacklist_characters="\x00"),
+        min_size=1,
+        max_size=30,
+    ),
+    telegram_notify=st.booleans(),
+    telegram_chat_id=st.one_of(st.none(), st.text(min_size=1, max_size=20, alphabet="0123456789-")),
+)
+def test_front_matter_defaults_merge(
+    keys_present: set,
+    event_name: str,
+    output_dir: str,
+    meeting_type: str,
+    telegram_notify: bool,
+    telegram_chat_id: str | None,
+):
+    """For any subset of recognized keys, verify merge produces correct TemplateConfig.
+
+    Keys present in front matter use the front matter value; absent keys use DEFAULTS.
+
+    Validates: Requirements 4.1, 4.4, 4.5
+    """
+    # Build the front matter dict with only the selected keys
+    values = {
+        "event_name": event_name,
+        "output_dir": output_dir,
+        "meeting_type": meeting_type,
+        "telegram_notify": telegram_notify,
+        "telegram_chat_id": telegram_chat_id,
+    }
+    front_matter = {k: values[k] for k in keys_present}
+
+    # If event_name or output_dir are absent, they default to "" which causes skip.
+    # We need both present and non-empty for the template to not be skipped.
+    if "event_name" not in keys_present or "output_dir" not in keys_present:
+        # Template will be skipped — verify it's not in results
+        with tempfile.TemporaryDirectory() as tmpdir:
+            fm_lines = ["---"]
+            for k, v in front_matter.items():
+                if isinstance(v, bool):
+                    fm_lines.append(f"{k}: {'true' if v else 'false'}")
+                elif v is None:
+                    fm_lines.append(f"{k}: null")
+                else:
+                    fm_lines.append(f'{k}: "{v}"')
+            fm_lines.append("---")
+            fm_lines.append("Template body content")
+            content = "\n".join(fm_lines)
+
+            filepath = os.path.join(tmpdir, "test_template.j2")
+            with open(filepath, "w") as f:
+                f.write(content)
+
+            results = discover_templates(tmpdir)
+            assert len(results) == 0, (
+                f"Expected template to be skipped when event_name or output_dir is absent, "
+                f"but got {len(results)} results. keys_present={keys_present}"
+            )
+        return
+
+    # Both required keys are present — template should be discovered
+    with tempfile.TemporaryDirectory() as tmpdir:
+        fm_lines = ["---"]
+        for k, v in front_matter.items():
+            if isinstance(v, bool):
+                fm_lines.append(f"{k}: {'true' if v else 'false'}")
+            elif v is None:
+                fm_lines.append(f"{k}: null")
+            else:
+                fm_lines.append(f'{k}: "{v}"')
+        fm_lines.append("---")
+        fm_lines.append("Template body content")
+        content = "\n".join(fm_lines)
+
+        filepath = os.path.join(tmpdir, "test_template.j2")
+        with open(filepath, "w") as f:
+            f.write(content)
+
+        results = discover_templates(tmpdir)
+        assert len(results) == 1, (
+            f"Expected 1 template, got {len(results)}. front_matter={front_matter}"
+        )
+
+        config = results[0]
+
+        # Verify each key: present keys use front matter value, absent keys use default
+        if "event_name" in keys_present:
+            assert config.event_name == event_name
+        else:
+            assert config.event_name == DEFAULTS["event_name"]
+
+        if "output_dir" in keys_present:
+            assert config.output_dir == output_dir
+        else:
+            assert config.output_dir == DEFAULTS["output_dir"]
+
+        if "meeting_type" in keys_present:
+            assert config.meeting_type == meeting_type
+        else:
+            assert config.meeting_type == DEFAULTS["meeting_type"]
+
+        if "telegram_notify" in keys_present:
+            assert config.telegram_notify == telegram_notify
+        else:
+            assert config.telegram_notify == DEFAULTS["telegram_notify"]
+
+        if "telegram_chat_id" in keys_present:
+            assert config.telegram_chat_id == telegram_chat_id
+        else:
+            assert config.telegram_chat_id == DEFAULTS["telegram_chat_id"]
+
+        # Verify template content and path are set correctly
+        assert config.template_content == "Template body content"
+        assert config.template_path == filepath
+
+
+# Feature: auto-agenda-generation, Property 1: Month time bounds are exact
+@settings(max_examples=100)
+@given(
+    year=st.integers(min_value=2000, max_value=2100),
+    month=st.integers(min_value=1, max_value=12),
+)
+def test_month_time_bounds_are_exact(year: int, month: int):
+    """For any year/month, compute_month_bounds returns timeMin/timeMax spanning exactly one month in UTC.
+
+    **Validates: Requirements 2.1**
+    """
+    from agenda_generator import compute_month_bounds
+
+    time_min, time_max = compute_month_bounds(year, month)
+
+    # Parse the returned strings
+    min_dt = datetime.datetime.fromisoformat(time_min.replace("Z", "+00:00"))
+    max_dt = datetime.datetime.fromisoformat(time_max.replace("Z", "+00:00"))
+
+    # timeMin should be the first day of the month at 00:00:00 UTC
+    assert min_dt.year == year
+    assert min_dt.month == month
+    assert min_dt.day == 1
+    assert min_dt.hour == 0
+    assert min_dt.minute == 0
+    assert min_dt.second == 0
+
+    # timeMax should be the first day of the NEXT month at 00:00:00 UTC
+    if month == 12:
+        expected_next_year = year + 1
+        expected_next_month = 1
+    else:
+        expected_next_year = year
+        expected_next_month = month + 1
+
+    assert max_dt.year == expected_next_year
+    assert max_dt.month == expected_next_month
+    assert max_dt.day == 1
+    assert max_dt.hour == 0
+    assert max_dt.minute == 0
+    assert max_dt.second == 0
+
+    # Verify the span is exactly one calendar month (timeMax - timeMin == days in month)
+    days_in_month = calendar.monthrange(year, month)[1]
+    assert (max_dt - min_dt).days == days_in_month
+
+
+# Feature: auto-agenda-generation, Property 2: Event name matching correctness
+@settings(max_examples=100)
+@given(
+    events=st.lists(
+        st.builds(
+            CalendarEvent,
+            summary=st.text(min_size=0, max_size=50),
+            date=st.dates(
+                min_value=datetime.date(2000, 1, 1),
+                max_value=datetime.date(2100, 12, 31),
+            ),
+        ),
+        min_size=0,
+        max_size=20,
+    ),
+    target_name=st.text(min_size=0, max_size=50),
+)
+def test_event_name_matching_correctness(events: list, target_name: str):
+    """For any list of CalendarEvents and target name, find_matching_event returns the first match or None.
+
+    **Validates: Requirements 2.2, 2.3**
+    """
+    from agenda_generator import find_matching_event
+
+    result = find_matching_event(events, target_name)
+
+    # Find the expected first matching event manually
+    expected = None
+    for event in events:
+        if event.summary == target_name:
+            expected = event
+            break
+
+    if expected is not None:
+        # Should return the first matching event
+        assert result is not None, (
+            f"Expected a match for target_name={target_name!r} but got None"
+        )
+        assert result is expected, (
+            f"Expected the FIRST matching event but got a different one"
+        )
+        assert result.summary == target_name
+    else:
+        # No match exists — result should be None
+        assert result is None, (
+            f"Expected None when no event matches target_name={target_name!r}, but got {result}"
+        )
+
+
+# Feature: auto-agenda-generation, Property 6: Date context variables are complete and correct
+@settings(max_examples=100)
+@given(
+    date=st.dates(
+        min_value=datetime.date(2000, 1, 1),
+        max_value=datetime.date(2100, 12, 31),
+    ),
+    meeting_type=st.text(min_size=1, max_size=50),
+    next_meeting_date=st.one_of(
+        st.none(),
+        st.dates(
+            min_value=datetime.date(2000, 1, 1),
+            max_value=datetime.date(2100, 12, 31),
+        ),
+    ),
+)
+def test_date_context_variables_complete_and_correct(
+    date: datetime.date, meeting_type: str, next_meeting_date: datetime.date | None
+):
+    """For any valid date, verify all context keys present with correct values.
+
+    **Validates: Requirements 7.2**
+    """
+    ctx = build_template_context(date, meeting_type, next_meeting_date)
+
+    # Verify all required keys are present
+    required_keys = {
+        "year", "month", "day", "month_name",
+        "day_ordinal", "day_plain", "date_iso", "meeting_type",
+        "next_meeting_date", "next_meeting_month_name",
+        "next_meeting_day_ordinal", "next_meeting_day_plain",
+        "next_meeting_weekday",
+    }
+    assert set(ctx.keys()) == required_keys, (
+        f"Expected keys {required_keys}, got {set(ctx.keys())}"
+    )
+
+    # Verify core date values
+    assert ctx["year"] == date.year
+    assert ctx["month"] == date.month
+    assert ctx["day"] == date.day
+    assert ctx["month_name"] == calendar.month_name[date.month]
+    assert ctx["day_ordinal"] == ordinal(date.day)
+    assert ctx["day_plain"] == str(date.day)
+    assert ctx["date_iso"] == date.isoformat()
+    assert ctx["meeting_type"] == meeting_type
+
+    # Verify next meeting date values
+    assert ctx["next_meeting_date"] == next_meeting_date
+    if next_meeting_date is not None:
+        assert ctx["next_meeting_month_name"] == calendar.month_name[next_meeting_date.month]
+        assert ctx["next_meeting_day_ordinal"] == ordinal(next_meeting_date.day)
+        assert ctx["next_meeting_day_plain"] == str(next_meeting_date.day)
+        assert ctx["next_meeting_weekday"] == calendar.day_name[next_meeting_date.weekday()]
+    else:
+        assert ctx["next_meeting_month_name"] == ""
+        assert ctx["next_meeting_day_ordinal"] == ""
+        assert ctx["next_meeting_day_plain"] == ""
+        assert ctx["next_meeting_weekday"] == ""
+
+
+# Feature: auto-agenda-generation, Property 9: Notification message contains meeting type and date
+@settings(max_examples=100)
+@given(
+    meeting_type=st.text(
+        alphabet=st.characters(whitelist_categories=("L", "N", "Zs", "Pd")),
+        min_size=1,
+        max_size=50,
+    ),
+    date=st.dates(
+        min_value=datetime.date(2000, 1, 1),
+        max_value=datetime.date(2100, 12, 31),
+    ),
+)
+def test_notification_message_contains_meeting_type_and_date(meeting_type: str, date: datetime.date):
+    """For any meeting type and valid date, the notification message contains both
+    the meeting type string and a human-readable representation of the date.
+
+    **Validates: Requirements 8.3**
+    """
+    from agenda_generator import build_notification_message
+
+    message = build_notification_message(meeting_type, date)
+
+    # Message must contain the meeting type
+    assert meeting_type in message, (
+        f"Message {message!r} does not contain meeting_type {meeting_type!r}"
+    )
+
+    # Message must contain a human-readable date representation
+    # At minimum: month name and year
+    month_name = calendar.month_name[date.month]
+    assert month_name in message, (
+        f"Message {message!r} does not contain month name {month_name!r}"
+    )
+    assert str(date.year) in message, (
+        f"Message {message!r} does not contain year {date.year}"
+    )
+
+
+# =============================================================================
+# Unit tests for main orchestrator (Task 8.2)
+# =============================================================================
+
+import sys
+from unittest.mock import patch, MagicMock
+
+import pytest
+
+from agenda_generator import main
+
+
+class TestMainEndToEnd:
+    """Test end-to-end flow with mocked Calendar API and temp directory."""
+
+    def test_main_end_to_end_with_mocked_calendar(self, tmp_path):
+        """Test full orchestrator flow: discovers template, fetches event,
+        renders agenda, writes file.
+
+        Validates: Requirements 3.1, 3.2
+        """
+        # Create a minimal board_meeting.j2 template in a temp templates dir
+        templates_dir = tmp_path / "templates"
+        templates_dir.mkdir()
+        output_dir = tmp_path / "board" / "agendas"
+
+        template_content = (
+            "---\n"
+            f'event_name: "Board Meeting"\n'
+            f'output_dir: "{output_dir}"\n'
+            f'meeting_type: "Board Meeting"\n'
+            "telegram_notify: false\n"
+            "---\n"
+            "# Board Meeting Agenda {{ month_name }} {{ day_plain }}, {{ year }}\n"
+        )
+        (templates_dir / "board_meeting.j2").write_text(template_content)
+
+        meeting_date = datetime.date(2025, 7, 21)
+        mock_event = CalendarEvent(summary="Board Meeting", date=meeting_date)
+        next_mock_event = CalendarEvent(summary="Board Meeting", date=datetime.date(2025, 8, 18))
+
+        env = {
+            "GOOGLE_SERVICE_ACCOUNT_JSON": "/tmp/fake_creds.json",
+            "GOOGLE_CALENDAR_ID": "test@group.calendar.google.com",
+        }
+
+        # Discover templates BEFORE patching
+        from agenda_generator import discover_templates as real_discover
+        discovered = real_discover(str(templates_dir))
+
+        with patch.dict(os.environ, env, clear=True), \
+             patch("agenda_generator.discover_templates") as mock_discover, \
+             patch("agenda_generator.get_events_in_month") as mock_get_events:
+
+            # First call = current month events, second call = next month events
+            mock_get_events.side_effect = [[mock_event], [next_mock_event]]
+            mock_discover.return_value = discovered
+
+            main()
+
+        # Verify the agenda file was created
+        expected_path = output_dir / "2025" / "agenda_2025-07-21.md"
+        assert expected_path.exists(), f"Expected agenda file at {expected_path}"
+
+        content = expected_path.read_text()
+        assert "# Board Meeting Agenda July 21, 2025" in content
+
+
+class TestMainIdempotency:
+    """Test that existing agenda files are not overwritten."""
+
+    def test_main_idempotency_skips_existing(self, tmp_path):
+        """When an agenda file already exists, main() should NOT overwrite it.
+
+        Validates: Requirements 3.1, 3.2
+        """
+        # Create a minimal template
+        templates_dir = tmp_path / "templates"
+        templates_dir.mkdir()
+        output_dir = tmp_path / "board" / "agendas"
+
+        template_content = (
+            "---\n"
+            f'event_name: "Board Meeting"\n'
+            f'output_dir: "{output_dir}"\n'
+            f'meeting_type: "Board Meeting"\n'
+            "telegram_notify: false\n"
+            "---\n"
+            "# Board Meeting Agenda {{ month_name }} {{ day_plain }}, {{ year }}\n"
+        )
+        (templates_dir / "board_meeting.j2").write_text(template_content)
+
+        # Pre-create the agenda file with known content
+        meeting_date = datetime.date(2025, 7, 21)
+        year_dir = output_dir / "2025"
+        year_dir.mkdir(parents=True)
+        existing_file = year_dir / "agenda_2025-07-21.md"
+        original_content = "# Pre-existing agenda content\n"
+        existing_file.write_text(original_content)
+
+        mock_event = CalendarEvent(summary="Board Meeting", date=meeting_date)
+
+        env = {
+            "GOOGLE_SERVICE_ACCOUNT_JSON": "/tmp/fake_creds.json",
+            "GOOGLE_CALENDAR_ID": "test@group.calendar.google.com",
+        }
+
+        # Discover templates BEFORE patching
+        from agenda_generator import discover_templates as real_discover
+        discovered = real_discover(str(templates_dir))
+
+        with patch.dict(os.environ, env, clear=True), \
+             patch("agenda_generator.discover_templates") as mock_discover, \
+             patch("agenda_generator.get_events_in_month") as mock_get_events:
+
+            mock_get_events.side_effect = [[mock_event], [mock_event]]
+            mock_discover.return_value = discovered
+
+            main()
+
+        # Verify the file was NOT overwritten
+        assert existing_file.read_text() == original_content
+
+
+class TestMainEnvVars:
+    """Test environment variable handling."""
+
+    def test_main_missing_required_env_vars_exits(self):
+        """main() should call sys.exit(1) when required env vars are missing.
+
+        Validates: Requirements 10.5
+        """
+        env = {}  # No env vars set
+
+        with patch.dict(os.environ, env, clear=True), \
+             pytest.raises(SystemExit) as exc_info:
+            main()
+
+        assert exc_info.value.code == 1
+
+    def test_main_missing_optional_env_vars_disables_telegram(self, tmp_path):
+        """When TELEGRAM_BOT_TOKEN/TELEGRAM_CHAT_ID are missing, Telegram
+        notifications should be disabled (send_telegram_notification not called).
+
+        Validates: Requirements 10.5
+        """
+        # Create a minimal template with telegram_notify: true
+        templates_dir = tmp_path / "templates"
+        templates_dir.mkdir()
+        output_dir = tmp_path / "board" / "agendas"
+
+        template_content = (
+            "---\n"
+            f'event_name: "Board Meeting"\n'
+            f'output_dir: "{output_dir}"\n'
+            f'meeting_type: "Board Meeting"\n'
+            "telegram_notify: true\n"
+            "---\n"
+            "# Board Meeting Agenda {{ month_name }} {{ day_plain }}, {{ year }}\n"
+        )
+        (templates_dir / "board_meeting.j2").write_text(template_content)
+
+        meeting_date = datetime.date(2025, 7, 21)
+        mock_event = CalendarEvent(summary="Board Meeting", date=meeting_date)
+
+        # Only required env vars, no Telegram vars
+        env = {
+            "GOOGLE_SERVICE_ACCOUNT_JSON": "/tmp/fake_creds.json",
+            "GOOGLE_CALENDAR_ID": "test@group.calendar.google.com",
+        }
+
+        # Discover templates BEFORE patching
+        from agenda_generator import discover_templates as real_discover
+        discovered = real_discover(str(templates_dir))
+
+        with patch.dict(os.environ, env, clear=True), \
+             patch("agenda_generator.discover_templates") as mock_discover, \
+             patch("agenda_generator.get_events_in_month") as mock_get_events, \
+             patch("agenda_generator.send_telegram_notification") as mock_telegram:
+
+            mock_get_events.side_effect = [[mock_event], [mock_event]]
+            mock_discover.return_value = discovered
+
+            main()
+
+        # Telegram should NOT have been called
+        mock_telegram.assert_not_called()
+
+
+class TestMainTelegramFailure:
+    """Test that Telegram failure does not fail the workflow."""
+
+    def test_main_telegram_failure_does_not_fail_workflow(self, tmp_path):
+        """When send_telegram_notification returns False, main() should
+        complete without raising an exception.
+
+        Validates: Requirements 8.6
+        """
+        # Create a minimal template with telegram_notify: true
+        templates_dir = tmp_path / "templates"
+        templates_dir.mkdir()
+        output_dir = tmp_path / "board" / "agendas"
+
+        template_content = (
+            "---\n"
+            f'event_name: "Board Meeting"\n'
+            f'output_dir: "{output_dir}"\n'
+            f'meeting_type: "Board Meeting"\n'
+            "telegram_notify: true\n"
+            "---\n"
+            "# Board Meeting Agenda {{ month_name }} {{ day_plain }}, {{ year }}\n"
+        )
+        (templates_dir / "board_meeting.j2").write_text(template_content)
+
+        meeting_date = datetime.date(2025, 7, 21)
+        mock_event = CalendarEvent(summary="Board Meeting", date=meeting_date)
+
+        env = {
+            "GOOGLE_SERVICE_ACCOUNT_JSON": "/tmp/fake_creds.json",
+            "GOOGLE_CALENDAR_ID": "test@group.calendar.google.com",
+            "TELEGRAM_BOT_TOKEN": "fake-bot-token",
+            "TELEGRAM_CHAT_ID": "-123456789",
+        }
+
+        # Discover templates BEFORE patching
+        from agenda_generator import discover_templates as real_discover
+        discovered = real_discover(str(templates_dir))
+
+        with patch.dict(os.environ, env, clear=True), \
+             patch("agenda_generator.discover_templates") as mock_discover, \
+             patch("agenda_generator.get_events_in_month") as mock_get_events, \
+             patch("agenda_generator.send_telegram_notification") as mock_telegram:
+
+            mock_get_events.side_effect = [[mock_event], [mock_event]]
+            mock_telegram.return_value = False  # Simulate Telegram failure
+            mock_discover.return_value = discovered
+
+            # Should NOT raise any exception
+            main()
+
+        # Verify Telegram was called (it was attempted)
+        mock_telegram.assert_called_once()
+
+        # Verify the agenda file was still created despite Telegram failure
+        expected_path = output_dir / "2025" / "agenda_2025-07-21.md"
+        assert expected_path.exists()
diff --git a/uv.lock b/uv.lock
new file mode 100644
index 0000000..078c145
--- /dev/null
+++ b/uv.lock
@@ -0,0 +1,692 @@
+version = 1
+revision = 3
+requires-python = ">=3.11"
+resolution-markers = [
+    "python_full_version >= '3.13'",
+    "python_full_version < '3.13'",
+]
+
+[[package]]
+name = "agenda-generator"
+version = "0.1.0"
+source = { virtual = "." }
+dependencies = [
+    { name = "google-api-python-client" },
+    { name = "google-auth" },
+    { name = "jinja2" },
+    { name = "python-frontmatter" },
+    { name = "requests" },
+]
+
+[package.dev-dependencies]
+dev = [
+    { name = "hypothesis" },
+    { name = "pytest" },
+]
+
+[package.metadata]
+requires-dist = [
+    { name = "google-api-python-client" },
+    { name = "google-auth" },
+    { name = "jinja2" },
+    { name = "python-frontmatter" },
+    { name = "requests" },
+]
+
+[package.metadata.requires-dev]
+dev = [
+    { name = "hypothesis" },
+    { name = "pytest" },
+]
+
+[[package]]
+name = "certifi"
+version = "2026.4.22"
+source = { registry = "https://pypi.org/simple" }
+sdist = { url = "https://files.pythonhosted.org/packages/25/ee/6caf7a40c36a1220410afe15a1cc64993a1f864871f698c0f93acb72842a/certifi-2026.4.22.tar.gz", hash = "sha256:8d455352a37b71bf76a79caa83a3d6c25afee4a385d632127b6afb3963f1c580", size = 137077, upload-time = "2026-04-22T11:26:11.191Z" }
+wheels = [
+    { url = "https://files.pythonhosted.org/packages/22/30/7cd8fdcdfbc5b869528b079bfb76dcdf6056b1a2097a662e5e8c04f42965/certifi-2026.4.22-py3-none-any.whl", hash = "sha256:3cb2210c8f88ba2318d29b0388d1023c8492ff72ecdde4ebdaddbb13a31b1c4a", size = 135707, upload-time = "2026-04-22T11:26:09.372Z" },
+]
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