diff --git a/app/__init__.py b/app/__init__.py
new file mode 100644
index 0000000..e33ba75
--- /dev/null
+++ b/app/__init__.py
@@ -0,0 +1 @@
+#app.__init__
\ No newline at end of file
diff --git a/app/bot.py b/app/bot.py
new file mode 100644
index 0000000..23b5311
--- /dev/null
+++ b/app/bot.py
@@ -0,0 +1,206 @@
+#app.bot
+
+import discord
+import aiohttp
+from datetime import datetime, timezone, timedelta
+from discord import app_commands
+from discord.ext import tasks
+
+from .config import settings
+from .db import init_db, insert_check, fetch_checks_since,fetch_month_checks
+from .utils import (
+    check_site, summarize_counts, get_site_names,
+    render_bar, compute_uptime, format_detection_reason,
+)
+ 
+TOKEN = settings.discord_secret_key
+ 
+# Convert Pydantic models → plain dicts once so the rest of bot.py is unchanged.
+MONITORED_SITES = [site.to_dict() for site in settings.monitored_sites]
+ 
+# SITE_CHOICES stays exactly the same — it reads from MONITORED_SITES:
+SITE_CHOICES = [
+    app_commands.Choice(name=site["name"], value=site["name"])
+    for site in MONITORED_SITES
+]
+
+intents = discord.Intents.default()
+client = discord.Client(intents=intents)
+tree = app_commands.CommandTree(client)
+session: aiohttp.ClientSession | None = None
+
+@client.event
+async def on_ready():
+    global session
+    init_db()
+
+    if session is None:
+        session = aiohttp.ClientSession(headers={"User-Agent": "VoteUptimeBot/1.0"})
+
+    if not poll_sites.is_running():
+        poll_sites.start()
+
+    await tree.sync()
+    print(f"Logged in as {client.user}")
+
+@tasks.loop(minutes=15)
+async def poll_sites():
+    now = datetime.now(timezone.utc).isoformat()
+ 
+    for site in MONITORED_SITES:
+        result = await check_site(session, site)
+        # Combine notes + detection_reason into the notes field so the DB
+        # schema doesn't need a migration.  error_type already carries reason.
+        notes = result["notes"]
+        if result.get("detection_reason") and not notes:
+            notes = format_detection_reason(result["detection_reason"])
+ 
+        insert_check(
+            site_name=site["name"],
+            checked_at=now,
+            http_status=result["http_status"],
+            latency_ms=result["latency_ms"],
+            result=result["result"],
+            error_type=result["error_type"],   # now carries detection_reason too
+            notes=notes,
+        )
+
+
+@poll_sites.before_loop
+async def before_poll_sites():
+    await client.wait_until_ready()
+
+class SiteNameTransformer(app_commands.Transformer):
+    async def transform(self, interaction: discord.Interaction, value: str) -> str:
+        if value not in get_site_names(MONITORED_SITES):
+            raise app_commands.AppCommandError(f"Unknown site: {value}")
+        return value
+
+uptime_group = app_commands.Group(name="uptime", description="Uptime tools")
+tree.add_command(uptime_group)
+
+
+@uptime_group.command(name="now", description="Show current configured sites")
+async def uptime_now(interaction: discord.Interaction):
+    lines = []
+    for site in MONITORED_SITES:
+        rows = fetch_checks_since(
+            site["name"], datetime.now(timezone.utc) - timedelta(hours=1)
+        )
+        if not rows:
+            lines.append(f"**{site['name']}**: no recent data")
+            continue
+ 
+        checked_at, result, http_status, latency_ms, error_type = rows[-1]
+ 
+        # Emoji prefix for quick scanning
+        emoji = {"up": "🟩", "degraded": "🟨", "down": "🟥"}.get(result, "⬛")
+ 
+        detail = f"{result.upper()} | status={http_status} | latency={latency_ms}ms"
+        if error_type:
+            detail += f" | reason={format_detection_reason(error_type)}"
+ 
+        lines.append(f"{emoji} **{site['name']}**: {detail}")
+ 
+    await interaction.response.send_message("\n".join(lines))
+
+
+SITE_CHOICES = [
+    app_commands.Choice(name=site["name"], value=site["name"])
+    for site in MONITORED_SITES
+]
+
+@uptime_group.command(name="day", description="Last 24 hours in 15-minute bars")
+@app_commands.describe(site="Site name")
+@app_commands.choices(site=SITE_CHOICES)
+async def uptime_day(
+    interaction: discord.Interaction,
+    site: app_commands.Transform[str, SiteNameTransformer],
+):
+    since = datetime.now(timezone.utc) - timedelta(hours=24)
+    rows = fetch_checks_since(site, since)
+    results = [row[1] for row in rows]
+
+    bar = render_bar(results[-96:]) if results else "⬛"
+    uptime = compute_uptime(results)
+    up, degraded, down = summarize_counts(results)
+
+    msg = (
+        f"**{site}** last 24h\n"
+        f"{bar}\n"
+        f"Uptime: **{uptime:.2f}%**\n"
+        f"Up: {up} | Degraded: {degraded} | Down: {down}"
+    )
+    await interaction.response.send_message(msg)
+
+
+@uptime_group.command(name="month", description="Current month summary")
+@app_commands.describe(site="Site name")
+@app_commands.choices(site=SITE_CHOICES)
+async def uptime_month(
+    interaction: discord.Interaction,
+    site: app_commands.Transform[str, SiteNameTransformer],
+):
+    now = datetime.now(timezone.utc)
+    rows = fetch_month_checks(site, now.year, now.month)
+
+    by_day: dict[str, list[str]] = {}
+    for checked_at, result, *_ in rows:
+        day_key = checked_at[:10]
+        by_day.setdefault(day_key, []).append(result)
+
+    day_bars = []
+    for day in sorted(by_day.keys()):
+        pct = compute_uptime(by_day[day])
+        if pct >= 99:
+            day_bars.append("🟩")
+        elif pct >= 95:
+            day_bars.append("🟨")
+        else:
+            day_bars.append("🟥")
+
+    all_results = [row[1] for row in rows]
+    uptime = compute_uptime(all_results)
+    up, degraded, down = summarize_counts(all_results)
+
+    msg = (
+        f"**{site}** {now.year}-{now.month:02d}\n"
+        f"{''.join(day_bars) if day_bars else '⬛'}\n"
+        f"Uptime: **{uptime:.2f}%**\n"
+        f"Up: {up} | Degraded: {degraded} | Down: {down}"
+    )
+    await interaction.response.send_message(msg)
+
+
+@uptime_group.command(name="summarize", description="Summarize current month for all sites")
+async def uptime_summarize(interaction: discord.Interaction):
+    now = datetime.now(timezone.utc)
+    lines = [f"**Monthly summary for {now.year}-{now.month:02d}**"]
+
+    for site in MONITORED_SITES:
+        rows = fetch_month_checks(site["name"], now.year, now.month)
+        results = [row[1] for row in rows]
+        uptime = compute_uptime(results)
+        up, degraded, down = summarize_counts(results)
+        lines.append(
+            f"{site['name']}: uptime={uptime:.2f}% | up={up} | degraded={degraded} | down={down}"
+        )
+
+    await interaction.response.send_message("\n".join(lines))
+
+
+@tree.command(name="incident", description="Placeholder incident review command")
+async def incident(interaction: discord.Interaction):
+    await interaction.response.send_message("Incident review command placeholder.")
+
+
+@tree.command(name="hello", description="Say hello")
+async def hello(interaction: discord.Interaction):
+    await interaction.response.send_message("Hello, world!")
+
+
+@tree.command(name="add", description="Add two numbers")
+async def add(interaction: discord.Interaction, a: float, b: float):
+    await interaction.response.send_message(f"Sum: {a + b}")
+
+client.run(TOKEN)
\ No newline at end of file
diff --git a/app/checker.py b/app/checker.py
new file mode 100644
index 0000000..5b7ea3c
--- /dev/null
+++ b/app/checker.py
@@ -0,0 +1,161 @@
+#app.checker
+
+import asyncio
+import time
+import aiohttp
+
+# Fingerprints that identify a Cloudflare interstitial/challenge/block page.
+# These appear in the response body even when the HTTP status is 200.
+CLOUDFLARE_FINGERPRINTS = [
+    "Just a moment",            # JS challenge page <title>
+    "cf-browser-verification",  # Legacy challenge <form> id
+    "cf_chl_opt",               # Challenge options JS variable
+    "cf-wrapper",               # <body> class on block/error pages
+    "Checking your browser",    # Human-verification copy
+    "Enable JavaScript and cookies to continue",  # CF IUAM page body
+    "Please Wait... | Cloudflare",  # Page title variant
+    "_cf_chl_f_tk",             # Hidden challenge token field
+]
+
+
+def _detect_cloudflare(body: str) -> bool:
+    """Return True if the response body looks like a Cloudflare intercept page."""
+    return any(fp in body for fp in CLOUDFLARE_FINGERPRINTS)
+
+
+def _check_keywords(body: str, keywords: list[str]) -> list[str]:
+    """Return any expected keywords that are absent from the body."""
+    return [kw for kw in keywords if kw not in body]
+
+
+class SiteChecker:
+    def __init__(self, session: aiohttp.ClientSession):
+        self.session = session
+
+    async def check(self, site: dict) -> dict:
+        """
+        Check a site dict with the following keys:
+            url             (str)       required
+            timeout_seconds (int)       default 10
+            expected_status (int)       default 200
+            expected_keywords (list)    default []   — strings that must appear in body
+            max_retries     (int)       default 1    — extra attempts on CF intercept
+
+        Returns a result dict:
+            http_status, latency_ms, result, error_type, notes, detection_reason
+        """
+        url             = site["url"]
+        timeout_secs    = site.get("timeout_seconds", 10)
+        expected_kws    = site.get("expected_keywords", [])
+        max_retries     = site.get("max_retries", 1)
+
+        last_result = None
+        for attempt in range(max_retries + 1):
+            last_result = await self._single_check(url, timeout_secs, expected_kws)
+
+            # Only retry when we hit a CF intercept and we have attempts left
+            if last_result["detection_reason"] == "cf_intercept" and attempt < max_retries:
+                await asyncio.sleep(2)
+                continue
+            break
+
+        return last_result
+
+    # ------------------------------------------------------------------
+    # Internal helpers
+    # ------------------------------------------------------------------
+
+    async def _single_check(
+        self,
+        url: str,
+        timeout_seconds: int,
+        expected_keywords: list[str],
+    ) -> dict:
+        started = time.perf_counter()
+        try:
+            timeout = aiohttp.ClientTimeout(total=timeout_seconds)
+            async with self.session.get(
+                url, timeout=timeout, allow_redirects=True
+            ) as resp:
+                latency_ms = int((time.perf_counter() - started) * 1000)
+                body = await resp.text(errors="replace")
+
+                # --- Cloudflare intercept check (fires even on HTTP 200) ---
+                if _detect_cloudflare(body):
+                    return {
+                        "http_status": resp.status,
+                        "latency_ms": latency_ms,
+                        "result": "degraded",
+                        "error_type": "cf_intercept",
+                        "detection_reason": "cf_intercept",
+                        "notes": "Cloudflare challenge/block page returned instead of real content",
+                    }
+
+                # --- HTTP status check ---
+                if 200 <= resp.status < 400:
+                    result = "up" if latency_ms < 3000 else "degraded"
+                    detection_reason = "slow_response" if result == "degraded" else None
+                elif resp.status in {429, 500, 502, 503, 504}:
+                    result = "degraded"
+                    detection_reason = f"http_{resp.status}"
+                else:
+                    result = "down"
+                    detection_reason = f"http_{resp.status}"
+
+                # --- Keyword content check (only meaningful when HTTP is OK) ---
+                if result in {"up", "degraded"} and expected_keywords:
+                    missing = _check_keywords(body, expected_keywords)
+                    if missing:
+                        result = "degraded"
+                        detection_reason = "missing_keywords"
+                        notes = f"Expected keywords not found in page: {missing}"
+                    else:
+                        notes = None
+                else:
+                    notes = None
+
+                return {
+                    "http_status": resp.status,
+                    "latency_ms": latency_ms,
+                    "result": result,
+                    "error_type": detection_reason,
+                    "detection_reason": detection_reason,
+                    "notes": notes,
+                }
+
+        except asyncio.TimeoutError:
+            return {
+                "http_status": None,
+                "latency_ms": None,
+                "result": "down",
+                "error_type": "timeout",
+                "detection_reason": "timeout",
+                "notes": "Request timed out",
+            }
+        except aiohttp.ClientConnectorError:
+            return {
+                "http_status": None,
+                "latency_ms": None,
+                "result": "down",
+                "error_type": "connection",
+                "detection_reason": "connection",
+                "notes": "Could not connect",
+            }
+        except aiohttp.ClientSSLError:
+            return {
+                "http_status": None,
+                "latency_ms": None,
+                "result": "down",
+                "error_type": "ssl",
+                "detection_reason": "ssl",
+                "notes": "SSL/TLS handshake error",
+            }
+        except Exception as e:
+            return {
+                "http_status": None,
+                "latency_ms": None,
+                "result": "down",
+                "error_type": "unknown",
+                "detection_reason": "unknown",
+                "notes": str(e),
+            }
\ No newline at end of file
diff --git a/app/config.py b/app/config.py
new file mode 100644
index 0000000..d2d38d1
--- /dev/null
+++ b/app/config.py
@@ -0,0 +1,53 @@
+# app.config
+
+from pydantic import BaseModel, HttpUrl, field_validator
+from pydantic_settings import BaseSettings, SettingsConfigDict
+
+
+class SiteConfig(BaseModel):
+    """Schema for a single monitored site."""
+    name: str
+    url: HttpUrl
+    timeout_seconds: int = 10
+    expected_status: int = 200
+    expected_keywords: list[str] = []
+    max_retries: int = 1
+
+    @field_validator("timeout_seconds")
+    @classmethod
+    def timeout_must_be_positive(cls, v: int) -> int:
+        if v <= 0:
+            raise ValueError("timeout_seconds must be a positive integer")
+        return v
+
+    def to_dict(self) -> dict:
+        """Return a plain dict compatible with check_site() in utils.py."""
+        return {
+            "name": self.name,
+            "url": str(self.url),
+            "timeout_seconds": self.timeout_seconds,
+            "expected_status": self.expected_status,
+            "expected_keywords": self.expected_keywords,
+            "max_retries": self.max_retries,
+        }
+
+
+class Settings(BaseSettings):
+    model_config = SettingsConfigDict(
+        env_file=".env",
+        env_file_encoding="utf-8",
+    )
+
+    # Discord
+    discord_secret_key: str = ""
+    discord_client_id: str = ""
+    discord_client_secret: str = ""
+
+    # Database
+    database_path: str = "uptime.db"
+
+    # Sites — stored as a JSON array string in .env:
+    monitored_sites: list[SiteConfig] = []
+
+
+settings = Settings()
\ No newline at end of file
diff --git a/app/db.py b/app/db.py
new file mode 100644
index 0000000..9350823
--- /dev/null
+++ b/app/db.py
@@ -0,0 +1,95 @@
+#app.db
+
+import sqlite3
+from datetime import datetime, timezone, timedelta
+
+from .config import settings
+DB_PATH = settings.database_path
+
+def init_db() -> None:
+    conn = sqlite3.connect(DB_PATH)
+    cur = conn.cursor()
+
+    cur.execute("""
+    CREATE TABLE IF NOT EXISTS site_checks (
+        id INTEGER PRIMARY KEY AUTOINCREMENT,
+        site_name TEXT NOT NULL,
+        checked_at TEXT NOT NULL,
+        http_status INTEGER,
+        latency_ms INTEGER,
+        result TEXT NOT NULL,
+        error_type TEXT,
+        notes TEXT
+    )
+    """)
+
+    cur.execute("""
+    CREATE TABLE IF NOT EXISTS monthly_reports (
+        id INTEGER PRIMARY KEY AUTOINCREMENT,
+        month_key TEXT NOT NULL,
+        site_name TEXT NOT NULL,
+        total_checks INTEGER NOT NULL,
+        up_checks INTEGER NOT NULL,
+        degraded_checks INTEGER NOT NULL,
+        down_checks INTEGER NOT NULL,
+        uptime_percent REAL NOT NULL,
+        created_at TEXT NOT NULL
+    )
+    """)
+
+    conn.commit()
+    conn.close()
+
+
+def insert_check(
+    site_name: str,
+    checked_at: str,
+    http_status: int | None,
+    latency_ms: int | None,
+    result: str,
+    error_type: str | None,
+    notes: str | None,
+) -> None:
+    conn = sqlite3.connect(DB_PATH)
+    cur = conn.cursor()
+    cur.execute("""
+    INSERT INTO site_checks (
+        site_name, checked_at, http_status, latency_ms, result, error_type, notes
+    ) VALUES (?, ?, ?, ?, ?, ?, ?)
+    """, (site_name, checked_at, http_status, latency_ms, result, error_type, notes))
+    conn.commit()
+    conn.close()
+
+
+def fetch_checks_since(site_name: str, since_dt: datetime) -> list[tuple]:
+    conn = sqlite3.connect(DB_PATH)
+    cur = conn.cursor()
+    cur.execute("""
+    SELECT checked_at, result, http_status, latency_ms, error_type
+    FROM site_checks
+    WHERE site_name = ? AND checked_at >= ?
+    ORDER BY checked_at ASC
+    """, (site_name, since_dt.isoformat()))
+    rows = cur.fetchall()
+    conn.close()
+    return rows
+
+
+def fetch_month_checks(site_name: str, year: int, month: int) -> list[tuple]:
+    start = datetime(year, month, 1, tzinfo=timezone.utc)
+    if month == 12:
+        end = datetime(year + 1, 1, 1, tzinfo=timezone.utc)
+    else:
+        end = datetime(year, month + 1, 1, tzinfo=timezone.utc)
+
+    conn = sqlite3.connect(DB_PATH)
+    cur = conn.cursor()
+    cur.execute("""
+    SELECT checked_at, result, http_status, latency_ms, error_type
+    FROM site_checks
+    WHERE site_name = ? AND checked_at >= ? AND checked_at < ?
+    ORDER BY checked_at ASC
+    """, (site_name, start.isoformat(), end.isoformat()))
+    rows = cur.fetchall()
+    conn.close()
+    return rows
\ No newline at end of file
diff --git a/app/utils.py b/app/utils.py
new file mode 100644
index 0000000..8447856
--- /dev/null
+++ b/app/utils.py
@@ -0,0 +1,88 @@
+#app.utils
+
+# check_site is the single entry point used by bot.py.
+# All HTTP / CF / keyword logic now lives in checker.py (SiteChecker).
+# This file keeps the pure helper functions for bar rendering, uptime
+# maths, and site-list utilities.
+
+import aiohttp
+from .checker import SiteChecker
+
+
+async def check_site(session: aiohttp.ClientSession, site: dict) -> dict:
+    """
+    Thin wrapper so bot.py doesn't need to import SiteChecker directly.
+
+    Accepts a site dict (same shape as MONITORED_SITES entries):
+        name, url, timeout_seconds, expected_status,
+        expected_keywords (optional list[str]),
+        max_retries       (optional int, default 1)
+    """
+    assert session is not None, "aiohttp session must be initialised before checking sites"
+    checker = SiteChecker(session)
+    return await checker.check(site)
+
+
+# ---------------------------------------------------------------------------
+# Pure helpers — no I/O
+# ---------------------------------------------------------------------------
+
+def summarize_counts(results: list[str]) -> tuple[int, int, int]:
+    """Return (up, degraded, down) counts from a list of result strings."""
+    up       = sum(1 for r in results if r == "up")
+    degraded = sum(1 for r in results if r == "degraded")
+    down     = sum(1 for r in results if r == "down")
+    return up, degraded, down
+
+
+def get_site_names(monitored_sites: list[dict]) -> list[str]:
+    return [site["name"] for site in monitored_sites]
+
+
+def render_bar(results: list[str]) -> str:
+    """
+    Convert a sequence of result strings into a coloured emoji bar.
+
+    Emoji key:
+      🟩 up       🟨 degraded / cf_intercept / missing_keywords
+      🟥 down     ⬛ no data
+    """
+    mapping = {
+        "up":       "🟩",
+        "degraded": "🟨",
+        "down":     "🟥",
+        "nodata":   "⬛",
+    }
+    return "".join(mapping.get(r, "⬛") for r in results)
+
+
+def compute_uptime(results: list[str]) -> float:
+    """
+    Return the percentage of checks that were fully 'up'.
+    'nodata' entries are excluded from the denominator.
+    Returns 0.0 when there are no considered results.
+    """
+    considered = [r for r in results if r != "nodata"]
+    if not considered:
+        return 0.0
+    good = sum(1 for r in considered if r == "up")
+    return (good / len(considered)) * 100
+
+
+def format_detection_reason(reason: str | None) -> str:
+    """Human-readable label for a detection_reason value."""
+    if not reason:
+        return ""
+    labels = {
+        "cf_intercept":      "Cloudflare intercept",
+        "missing_keywords":  "Content check failed",
+        "slow_response":     "Slow response (>3 s)",
+        "timeout":           "Request timed out",
+        "connection":        "Connection refused",
+        "ssl":               "SSL/TLS error",
+        "unknown":           "Unknown error",
+    }
+    # http_NNN codes
+    if reason.startswith("http_"):
+        return f"HTTP {reason[5:]}"
+    return labels.get(reason, reason)
\ No newline at end of file