Add opt-in monthly email recaps with scheduling and delivery history

backend/app/db.py

@@ -733,6 +733,8 @@ def init_db() -> None:
             conn.execute("PRAGMA optimize")
         except sqlite3.OperationalError:
             pass
+        from .services.recap_store import init_schema as init_recap_schema
+        init_recap_schema(conn)
     _backfill_auth_providers()
     ensure_admin_user()
     _backfill_request_repairs()

backend/app/main.py

@@ -29,8 +29,10 @@ from .routers.portal import router as portal_router
 from .routers.operations import router as operations_router
 from .routers.insights import router as insights_router
 from .routers.identities import router as identities_router
+from .routers.recaps import router as recaps_router
 from .services.jellyfin_sync import run_daily_jellyfin_sync
 from .services.issue_resolution import run_issue_confirmation_loop
+from .services.email_recaps import run_email_recap_loop
 from .services.operation_progress import (
     begin_operation,
     finish_operation,
@@ -267,6 +269,7 @@ async def startup() -> None:
     _launch_background_task("requests-full-sync", run_daily_requests_full_sync)
     _launch_background_task("db-cleanup", run_daily_db_cleanup)
     _launch_background_task("issue-confirmation", run_issue_confirmation_loop)
+    _launch_background_task("email-recaps", run_email_recap_loop)
     logger.info("startup complete")
 
 
@@ -284,3 +287,4 @@ app.include_router(portal_router)
 app.include_router(operations_router)
 app.include_router(insights_router)
 app.include_router(identities_router)
+app.include_router(recaps_router)

backend/app/routers/recaps.py

@@ -0,0 +1,133 @@
+from datetime import datetime, timezone
+from typing import Literal
+from urllib.parse import urlsplit
+from uuid import UUID
+
+from fastapi import APIRouter, Depends, HTTPException, Query, Response
+from pydantic import BaseModel, ConfigDict, Field, field_validator
+
+from ..auth import get_current_user, require_admin
+from ..services import email_recaps as recaps, recap_store as store
+
+
+def no_cache(response: Response):
+    response.headers["Cache-Control"] = "no-store"
+
+
+router = APIRouter(tags=["email-recaps"], dependencies=[Depends(no_cache)])
+
+
+class StrictPayload(BaseModel):
+    model_config = ConfigDict(extra="forbid")
+
+
+class Preference(StrictPayload):
+    enabled: bool
+
+
+class RecapSettings(StrictPayload):
+    enabled: bool
+    day: int = Field(ge=1, le=28)
+    hour: int = Field(ge=0, le=23)
+    public_url: str = Field(max_length=500)
+
+    @field_validator("public_url")
+    @classmethod
+    def origin_only(cls, value: str) -> str:
+        value = value.strip().rstrip('/')
+        if not value:
+            return value
+        try:
+            url = urlsplit(value)
+            port = url.port
+        except ValueError as exc:
+            raise ValueError("Enter the public Magent address, such as https://magent.example.com.") from exc
+        if (url.scheme not in {"http", "https"} or not url.hostname or url.username or url.password
+                or url.path or url.query or url.fragment or any(char.isspace() or ord(char) < 33 for char in value)
+                or any(char in value for char in '<>"\\') or (port is not None and port < 1)):
+            raise ValueError("Enter a http(s) Magent address without a path, credentials or query.")
+        return value
+
+
+class TestEmail(StrictPayload):
+    month: str | None = Field(default=None, pattern=r"^[0-9]{4}-[0-9]{2}$")
+    request_id: UUID
+
+
+class TokenAction(StrictPayload):
+    token: str = Field(min_length=40, max_length=100, pattern=r"^[A-Za-z0-9_-]+$")
+    action: Literal["confirm", "unsubscribe"]
+
+
+def error(exc: recaps.RecapError):
+    raise HTTPException(exc.status, exc.detail) from exc
+
+
+@router.get("/profile/email-recaps")
+def preferences(user: dict = Depends(get_current_user)) -> dict:
+    try:
+        return recaps.preferences(user)
+    except recaps.RecapError as exc:
+        error(exc)
+
+
+@router.put("/profile/email-recaps")
+async def preference(payload: Preference, user: dict = Depends(get_current_user)) -> dict:
+    try:
+        if payload.enabled:
+            return await recaps.subscribe(user)
+        store.disable(recaps.current_account(user)["id"])
+        return recaps.preferences(user)
+    except recaps.RecapError as exc:
+        error(exc)
+
+
+@router.post("/email-recaps/check")
+def check_token(payload: TokenAction) -> dict:
+    try:
+        return recaps.token_action(payload.token, payload.action)
+    except recaps.RecapError as exc:
+        error(exc)
+
+
+@router.post("/email-recaps/confirm")
+def apply_token(payload: TokenAction) -> dict:
+    try:
+        return recaps.token_action(payload.token, payload.action, apply=True)
+    except recaps.RecapError as exc:
+        error(exc)
+
+
+@router.get("/admin/email-recaps")
+def overview(offset: int = Query(default=0, ge=0), user: dict = Depends(require_admin)) -> dict:
+    ready, detail = recaps.delivery_ready()
+    months = recaps.month_periods(None, datetime.now(timezone.utc))["available_months"][1:]
+    return {"settings": store.settings(), "ready": ready, "detail": detail, "months": months,
+            "worker_enabled": recaps.worker_enabled(), **store.history(offset=offset)}
+
+
+@router.put("/admin/email-recaps")
+def settings(payload: RecapSettings, user: dict = Depends(require_admin)) -> dict:
+    if payload.enabled:
+        # Validate against the proposed URL without writing any partial settings.
+        ready, detail = recaps.smtp_email_config_ready()
+        runtime = recaps.get_runtime_settings()
+        if not payload.public_url or not ready or not recaps.worker_enabled() or not runtime.jellystat_base_url or not runtime.jellystat_api_key:
+            raise HTTPException(409, "Set the public address, enable SMTP email and connect Jellystat before starting the schedule." if ready else detail)
+    return store.save_settings(payload.model_dump(), datetime.now(timezone.utc))
+
+
+@router.get("/admin/email-recaps/preview")
+async def preview(month: str | None = Query(default=None, max_length=7, pattern=r"^[0-9]{4}-[0-9]{2}$"), user: dict = Depends(require_admin)) -> dict:
+    try:
+        return await recaps.preview(user, month)
+    except recaps.RecapError as exc:
+        error(exc)
+
+
+@router.post("/admin/email-recaps/test", status_code=202)
+def test_email(payload: TestEmail, user: dict = Depends(require_admin)) -> dict:
+    try:
+        return recaps.queue_test(user, payload.month, str(payload.request_id))
+    except recaps.RecapError as exc:
+        error(exc)

backend/app/services/email_recaps.py

@@ -0,0 +1,243 @@
+"""Opt-in monthly recaps. Scheduling and delivery are safe to run in multiple workers."""
+
+import asyncio
+import logging
+import os
+import time
+import uuid
+from datetime import datetime, timezone
+from urllib.parse import urlencode
+
+from .. import db
+from ..clients.jellystat import HistoryLimitError, JellystatError
+from ..runtime import get_runtime_settings
+from . import recap_email as mail, recap_store as store
+from .invite_email import smtp_email_config_ready
+from .jellyfin_identity import linked_user_id, source_key
+from .monthly_reports import get_monthly_report, month_periods
+
+logger = logging.getLogger(__name__)
+
+
+class RecapError(Exception):
+    def __init__(self, detail: str, status: int = 409):
+        self.detail, self.status = detail, status
+        super().__init__(detail)
+
+
+def worker_enabled() -> bool:
+    return os.environ.get("BACKGROUND_TASKS_ENABLED", "true").lower() != "false"
+
+
+def delivery_ready() -> tuple[bool, str]:
+    config = store.settings()
+    if not config["public_url"]:
+        return False, "Set the public Magent address for email links."
+    ready, detail = smtp_email_config_ready()
+    if not ready:
+        return False, detail
+    runtime = get_runtime_settings()
+    if not runtime.jellystat_base_url or not runtime.jellystat_api_key:
+        return False, "Connect Jellystat to generate viewing recaps."
+    if not worker_enabled():
+        return False, "Background automation is paused on this server."
+    return True, "Email delivery is configured."
+
+
+def current_account(user: dict) -> dict:
+    account = db.get_user_by_username(user.get("username", ""))
+    if not account or account.get("is_blocked") or account.get("is_expired"):
+        raise RecapError("This account cannot receive viewing recaps.", 403)
+    return account
+
+
+def binding_matches(sub: dict, account: dict) -> bool:
+    runtime = get_runtime_settings()
+    return bool(account and not account.get("is_blocked") and not account.get("is_expired")
+                and mail.valid_email(account.get("email"))
+                and account["email"].strip().casefold() == sub["email"].strip().casefold()
+                and source_key(runtime.jellyfin_base_url) == sub["identity_source"]
+                and linked_user_id(account["username"], runtime.jellyfin_base_url) == sub["identity_id"])
+
+
+def active_subscription(account: dict) -> dict | None:
+    sub = store.subscription(account["id"])
+    if sub and sub["state"] != "off" and not binding_matches(sub, account):
+        store.disable(account["id"])
+        sub = store.subscription(account["id"])
+    return sub
+
+
+def preferences(user: dict) -> dict:
+    account = current_account(user)
+    sub = active_subscription(account)
+    config = store.settings()
+    ready, detail = delivery_ready()
+    runtime = get_runtime_settings()
+    linked = bool(linked_user_id(account["username"], runtime.jellyfin_base_url))
+    email = mail.valid_email(account.get("email"))
+    state = sub["state"] if sub else "off"
+    if state == "pending" and sub["confirmation_expires"] <= time.time():
+        state = "expired"
+    return {"state": state, "email": account.get("email"), "can_subscribe": ready and linked and bool(email),
+            "detail": detail if not ready else "Save a valid email address in your profile." if not email else
+                      "Your Jellyfin account needs a saved identity link." if not linked else "Your monthly story, in your inbox.",
+            "schedule_enabled": config["enabled"], "next_send_at": config["next_send_at"],
+            "day": config["day"], "hour": config["hour"], "timezone": "UTC",
+            "resend_after": (sub["requested_at"] + 300) if sub else None}
+
+
+async def subscribe(user: dict) -> dict:
+    account = current_account(user)
+    preference = preferences(user)
+    if preference["state"] == "enabled":
+        return preference
+    if not preference["can_subscribe"]:
+        raise RecapError(preference["detail"])
+    config = store.settings()
+    runtime = get_runtime_settings()
+    try:
+        token = store.request_confirmation(account, source_key(runtime.jellyfin_base_url),
+                                           linked_user_id(account["username"], runtime.jellyfin_base_url), time.time())
+    except ValueError as exc:
+        raise RecapError(str(exc), 429) from exc
+    url = f"{config['public_url']}/email-recaps#" + urlencode({"action": "confirm", "token": token})
+    rendered = mail.render_confirmation(account["username"], url)
+    try:
+        await asyncio.to_thread(mail.send_email, account["email"].strip(), rendered,
+                                mail.message_id(uuid.uuid4().hex, config["public_url"]))
+    except mail.DeliveryError as exc:
+        raise RecapError("Could not confirm delivery of the verification email. Check your inbox; you can request another in five minutes.", 502) from exc
+    return {**preferences(user), "message": "Check your inbox and confirm within 24 hours to turn on monthly recaps."}
+
+
+def token_action(token: str, action: str, *, apply: bool = False) -> dict:
+    sub = store.token_subscription(token, action)
+    if not sub:
+        raise RecapError("This email link is invalid or has already been used. Open Profile to manage your recaps.", 410)
+    if action == "unsubscribe":
+        if apply:
+            store.disable(sub["user_id"])
+        return {"action": action, "state": "off" if apply or sub["state"] == "off" else "ready"}
+    account = db.get_user_by_id(sub["user_id"])
+    if (sub["state"] != "pending" or sub["confirmation_expires"] <= time.time()
+            or not binding_matches(sub, account)):
+        raise RecapError("This confirmation has expired or your account details changed. Request a new link from Profile.", 410)
+    if apply and not store.confirm(sub, time.time()):
+        raise RecapError("This confirmation is no longer available. Request a new link from Profile.", 410)
+    return {"action": action, "state": "enabled" if apply else "ready"}
+
+
+def completed_month(month: str | None) -> str:
+    try:
+        period = month_periods(month, datetime.now(timezone.utc))
+    except ValueError as exc:
+        raise RecapError(str(exc), 422) from exc
+    if period["is_partial"]:
+        raise RecapError("Choose a completed month for an email recap.", 422)
+    return period["month"]
+
+
+async def preview(user: dict, month: str | None) -> dict:
+    account = current_account(user)
+    selected = completed_month(month)
+    config = store.settings()
+    if not config["public_url"]:
+        raise RecapError("Save the public Magent address before previewing an email.")
+    try:
+        report = await asyncio.wait_for(get_monthly_report(account, selected), timeout=180)
+    except HistoryLimitError as exc:
+        raise RecapError("This report exceeds Jellystat's history limit. No partial recap was generated.", 422) from exc
+    except (JellystatError, TimeoutError) as exc:
+        raise RecapError("Your report is temporarily unavailable. Please try again shortly.", 502) from exc
+    if report["state"] != "ready":
+        raise RecapError("Connect Jellystat and link your Jellyfin account to preview your recap.")
+    return {"month": selected, "email": account.get("email"), **mail.render_recap(
+        report, account["username"], config["public_url"], config["public_url"] + "/profile#monthly-recaps")}
+
+
+def queue_test(user: dict, month: str | None, request_id: str) -> dict:
+    account = current_account(user)
+    ready, detail = delivery_ready()
+    if not ready:
+        raise RecapError(detail)
+    sub = active_subscription(account)
+    if not sub or sub["state"] != "enabled":
+        raise RecapError("Turn on email recaps and confirm your email in Profile before sending a personal test.")
+    selected = completed_month(month)
+    try:
+        delivery_id = store.enqueue_test(sub, selected, request_id, store.settings()["public_url"], time.time())
+    except ValueError as exc:
+        raise RecapError(str(exc), 429) from exc
+    return {"id": delivery_id, "message": "Test queued for your confirmed email. Check delivery history for the result."}
+
+
+def eligible_delivery(delivery: dict) -> tuple[dict, dict]:
+    account = db.get_user_by_id(delivery["user_id"])
+    sub = active_subscription(account) if account else None
+    config = store.settings()
+    ready, _ = delivery_ready()
+    if (not ready or not sub or sub["state"] != "enabled" or sub["version"] != delivery["subscription_version"]
+            or sub["email"] != delivery["email"] or not binding_matches(sub, account)
+            or config["public_url"] != delivery["public_url"]
+            or (delivery["kind"] == "scheduled" and not config["enabled"])):
+        raise mail.DeliveryCancelled()
+    return account, sub
+
+
+async def process_delivery(delivery: dict) -> None:
+    state, detail, delay = "failed", "Could not prepare the recap. Check the report and email settings.", 0
+    try:
+        account, sub = eligible_delivery(delivery)
+        report = await asyncio.wait_for(get_monthly_report(account, delivery["month"]), timeout=180)
+        if report["state"] != "ready" or report["is_partial"]:
+            raise mail.DeliveryError("failed", "A complete personal report is not available.")
+        unsubscribe = f"{delivery['public_url']}/email-recaps#" + urlencode({"action": "unsubscribe", "token": sub["unsubscribe_token"]})
+        rendered = mail.render_recap(report, account["username"], delivery["public_url"], unsubscribe, test=delivery["kind"] == "test")
+
+        def before_data():
+            eligible_delivery(delivery)
+            if not store.begin_sending(delivery, time.time()):
+                raise mail.DeliveryCancelled()
+
+        await asyncio.to_thread(mail.send_email, delivery["email"], rendered,
+                                mail.message_id(delivery["id"], delivery["public_url"]), before_data)
+        state, detail = "sent", "Accepted by the mail server."
+    except mail.DeliveryCancelled:
+        state, detail = "cancelled", "Consent, account details or email configuration changed."
+    except HistoryLimitError:
+        state, detail = "failed", "Jellystat's history limit was reached. No partial recap was sent."
+    except (JellystatError, TimeoutError):
+        state, detail = "retry", "Viewing history is temporarily unavailable."
+    except mail.DeliveryError as exc:
+        state, detail = exc.state, exc.detail
+    except Exception as exc:
+        # Do not expose provider errors or private report content in history/logs.
+        logger.error("recap delivery error id=%s type=%s", delivery["id"], type(exc).__name__)
+        row = store.read_one("SELECT state FROM email_recap_deliveries WHERE id=?", (delivery["id"],))
+        if row and row["state"] == "sending":
+            state, detail = "unknown", "Delivery outcome is unknown; check the mail server."
+    if state == "retry":
+        if delivery["attempts"] >= 3:
+            state, detail = "failed", detail + " Stopped after three attempts."
+        else:
+            delay = 300 if delivery["attempts"] == 1 else 1800
+    store.finish(delivery, state, detail, time.time(), delay)
+
+
+async def run_once() -> None:
+    store.enqueue_due(datetime.now(timezone.utc))
+    for _ in range(10):
+        delivery = store.claim_delivery(time.time())
+        if not delivery:
+            break
+        await process_delivery(delivery)
+
+
+async def run_email_recap_loop() -> None:
+    while True:
+        try:
+            await run_once()
+        except Exception as exc:
+            logger.error("email recap worker failed type=%s", type(exc).__name__)
+        await asyncio.sleep(30)

backend/app/services/recap_email.py

@@ -0,0 +1,172 @@
+"""Personal recap email rendering and SMTP delivery with explicit acceptance tracking."""
+
+import html
+import re
+import smtplib
+import ssl
+from contextlib import suppress
+from datetime import datetime
+from email.message import EmailMessage
+from email.policy import SMTP as SMTP_POLICY
+from email.utils import formataddr, formatdate
+from urllib.parse import urlsplit
+
+from ..runtime import get_runtime_settings
+
+
+class DeliveryError(Exception):
+    def __init__(self, state: str, detail: str):
+        self.state, self.detail = state, detail
+        super().__init__(detail)
+
+
+class DeliveryCancelled(Exception):
+    pass
+
+
+def valid_email(value: str | None) -> str | None:
+    value = str(value or "").strip()
+    if (len(value) <= 254 and re.fullmatch(r"[^@\s<>;,\"\\]+@[^@\s<>;,\"\\]+\.[^@\s<>;,\"\\]+", value)
+            and all(32 < ord(char) < 127 for char in value)):
+        return value
+    return None
+
+
+def month_label(value: str) -> str:
+    return datetime.strptime(value, "%Y-%m").strftime("%B %Y")
+
+
+def number(value: float) -> str:
+    return f"{value:,.0f}"
+
+
+def document(*, title: str, intro: str, content: str, action: str, url: str, footer: str) -> str:
+    esc = html.escape
+    return f'''<!doctype html><html lang="en"><head><meta charset="utf-8"><meta name="viewport" content="width=device-width, initial-scale=1"><meta name="color-scheme" content="dark"><title>{esc(title)}</title><style>@media(max-width:280px){{.email-metrics td{{display:block!important;width:auto!important;padding:16px 0!important}}.email-metrics tr{{display:block!important}}}}</style></head>
+<body style="margin:0;padding:0;background:#131315;color:#e5e1e4;font-family:Arial,Helvetica,sans-serif">
+<table role="presentation" width="100%" cellpadding="0" cellspacing="0" style="background:#131315"><tr><td align="center" style="padding:24px 12px">
+<table role="presentation" width="600" cellpadding="0" cellspacing="0" style="width:100%;max-width:600px;table-layout:fixed;background:#1c1b1d;border:1px solid #363338;border-radius:16px">
+<tr><td style="padding:32px 24px 8px;color:#c7bdff;font-size:12px;letter-spacing:2px;font-weight:bold">MAGENT <span style="color:#918b98;letter-spacing:0">/ YOUR MONTH IN VIEWING</span></td></tr>
+<tr><td style="padding:12px 24px"><h1 style="margin:0 0 16px;font-size:32px;line-height:1.2;color:#f3eef6">{esc(title)}</h1><p style="margin:0;color:#bdb6c3;font-size:15px;line-height:1.7;overflow-wrap:anywhere">{esc(intro)}</p></td></tr>
+<tr><td style="padding:12px 24px">{content}</td></tr>
+<tr><td style="padding:20px 24px 32px"><a href="{esc(url, quote=True)}" style="display:inline-block;padding:15px 22px;border-radius:8px;background:#c7bdff;color:#211b30;text-decoration:none;font-size:14px;font-weight:bold">{esc(action)} &#8599;</a></td></tr>
+</table><table role="presentation" width="600" style="width:100%;max-width:600px"><tr><td style="padding:22px 18px;color:#a69fac;font-size:12px;line-height:1.7;text-align:center">{footer}</td></tr></table>
+</td></tr></table></body></html>'''
+
+
+def render_confirmation(username: str, url: str) -> dict:
+    title = "Your month, delivered."
+    intro = f"Hi {username}, confirm this email address to receive your personal monthly viewing recap from Magent."
+    text = f"{intro}\n\nConfirm email recaps: {url}\n\nThis link expires in 24 hours. If you did not request this, ignore this email. No viewing history will be emailed until you confirm."
+    body = document(title=title, intro=intro,
+                    content='<p style="color:#bdb6c3;font-size:14px;line-height:1.7">Minutes watched, movies, episodes, your longest run and requests — with a link to your full monthly report.</p>',
+                    action="Confirm email recaps", url=url,
+                    footer="This link expires in 24 hours. If you did not request this, ignore this email.<br>No viewing history will be emailed until you confirm.")
+    return {"subject": "Confirm your Magent email recaps", "body_text": text, "body_html": body}
+
+
+def render_recap(report: dict, username: str, public_url: str, unsubscribe_url: str, *, test: bool = False) -> dict:
+    esc = html.escape
+    month = month_label(report["month"])
+    previous = month_label(report["comparison_month"])
+    summary = report["summary"]
+    metrics = (("Minutes watched", "minutes", summary["minutes"]), ("Movies played", "movies", summary["movies"]),
+               ("Episodes played", "episodes", summary["episodes"]), ("Requests made", "requests", report["requests"]["total"]))
+    cells, lines = [], []
+    for label, key, value in metrics:
+        change = report["changes"][key]
+        difference = change["difference"]
+        comparison = ("No change" if difference == 0 else f"{'+' if difference > 0 else '−'}{number(abs(difference))}")
+        if change["percent"] is not None and difference:
+            comparison += f" ({'+' if difference > 0 else '−'}{abs(change['percent']):g}%)"
+        comparison += f" from {previous}"
+        lines.append(f"{label}: {number(value)}. {comparison}.")
+        cells.append(f'<td width="50%" valign="top" style="padding:16px 10px;border-bottom:1px solid #363338"><span style="color:#bdb6c3;font-size:12px">{label}</span><br><strong style="display:block;margin:10px 0;color:#e0d8ff;font-size:30px">{number(value)}</strong><span style="color:#a69fac;font-size:11px;line-height:1.6">{esc(comparison)}</span></td>')
+    content = '<table role="presentation" class="email-metrics" width="100%" cellpadding="0" cellspacing="0" style="table-layout:fixed"><tr>' + ''.join(cells[:2]) + '</tr><tr>' + ''.join(cells[2:]) + '</tr></table>'
+    habit = f"{number(summary['active_days'])} days watched · {number(summary['longest_streak'])}-day longest run"
+    content += f'<p style="color:#e5e1e4;font-size:14px;line-height:1.7;margin:24px 0">{esc(habit)}</p>'
+    top = report.get("top_titles", [])[:3]
+    if top:
+        content += '<h2 style="font-size:18px;color:#e5e1e4;margin:24px 0 8px">Your most watched</h2>'
+        for item in top:
+            content += f'<p style="font-size:14px;line-height:1.6;color:#e5e1e4;margin:12px 0;overflow-wrap:anywhere">{esc(item["title"])}<br><span style="font-size:12px;color:#a69fac">{number(item["minutes"])} minutes · {number(item["plays"])} plays</span></p>'
+    else:
+        content += '<p style="font-size:14px;color:#bdb6c3;line-height:1.7">No viewing was recorded this month. Your requests are still included.</p>'
+    report_url = f"{public_url}/insights/reports?month={report['month']}"
+    intro = f"Hi {username}, here’s your {month} in viewing. A little look back at the stories you spent time with."
+    footer = f'You opted in to personal monthly recaps from Magent.<br>Based on retained Jellystat history. Calendar months use UTC; request statuses are current.<br><a href="{esc(unsubscribe_url, quote=True)}" style="color:#c7bdff">Unsubscribe from recaps</a> · <a href="{esc(public_url + "/profile#monthly-recaps", quote=True)}" style="color:#c7bdff">Email preferences</a>'
+    if test:
+        intro = "This is your test recap. " + intro
+    body = document(title=month, intro=intro, content=content, action="Explore your full report", url=report_url, footer=footer)
+    text = '\n'.join([intro, '', *lines, '', habit, '', 'Most watched:',
+                      *(f"{item['title']}: {number(item['minutes'])} minutes" for item in top), '',
+                      f"Your full report: {report_url}", '', 'Based on retained Jellystat history. Calendar months use UTC; request statuses are current.',
+                      f"Unsubscribe from recaps: {unsubscribe_url}", f"Email preferences: {public_url}/profile#monthly-recaps"])
+    return {"subject": f"{'[Test] ' if test else ''}Your {month} in viewing · Magent", "body_text": text, "body_html": body}
+
+
+def send_email(recipient: str, rendered: dict, message_id: str, before_data=lambda: None) -> None:
+    """Return only after SMTP accepts DATA. Never retry an ambiguous DATA disconnect.
+
+    A stable Message-ID aids diagnosis; it is not an SMTP deduplication guarantee.
+    See RFC 5321 §4.5.3.2.6 and Python's smtplib exception definitions.
+    """
+    runtime = get_runtime_settings()
+    sender = valid_email(runtime.magent_notify_email_from_address)
+    if not sender or not valid_email(recipient):
+        raise DeliveryError("failed", "A valid sender and recipient email are required.")
+    message = EmailMessage(policy=SMTP_POLICY)
+    message["From"] = formataddr((str(runtime.magent_notify_email_from_name or "Magent").replace('\r', '').replace('\n', ''), sender))
+    message["To"], message["Subject"] = recipient, rendered["subject"]
+    message["Date"], message["Message-ID"] = formatdate(localtime=False), message_id
+    message["Auto-Submitted"], message["X-Auto-Response-Suppress"] = "auto-generated", "All"
+    message.set_content(rendered["body_text"])
+    message.add_alternative(rendered["body_html"], subtype="html")
+    payload = message.as_bytes()
+    smtp, stage = None, "connect"
+    try:
+        kwargs = {"timeout": 30, "local_hostname": sender.split('@', 1)[1]}
+        if runtime.magent_notify_email_use_ssl:
+            smtp = smtplib.SMTP_SSL(runtime.magent_notify_email_smtp_host, runtime.magent_notify_email_smtp_port,
+                                    context=ssl.create_default_context(), **kwargs)
+        else:
+            smtp = smtplib.SMTP(runtime.magent_notify_email_smtp_host, runtime.magent_notify_email_smtp_port, **kwargs)
+        smtp.ehlo_or_helo_if_needed()
+        if runtime.magent_notify_email_use_tls and not runtime.magent_notify_email_use_ssl:
+            smtp.starttls(context=ssl.create_default_context())
+            smtp.ehlo()
+        if runtime.magent_notify_email_smtp_username:
+            smtp.login(runtime.magent_notify_email_smtp_username, runtime.magent_notify_email_smtp_password)
+        code, reply = smtp.mail(sender)
+        if code != 250:
+            raise smtplib.SMTPResponseException(code, reply)
+        code, reply = smtp.rcpt(recipient)
+        if code not in (250, 251):
+            raise smtplib.SMTPResponseException(code, reply)
+        before_data()
+        stage = "data"
+        code, reply = smtp.data(payload)
+        if code != 250:
+            raise smtplib.SMTPDataError(code, reply)
+        stage = "accepted"
+    except smtplib.SMTPResponseException as exc:
+        state = "retry" if 400 <= exc.smtp_code < 500 else "failed"
+        raise DeliveryError(state, f"Mail server returned SMTP {exc.smtp_code}.") from exc
+    except (ssl.SSLError, smtplib.SMTPNotSupportedError, UnicodeError, ValueError) as exc:
+        raise DeliveryError("failed", "Check the SMTP security and sender settings.") from exc
+    except (OSError, smtplib.SMTPException) as exc:
+        state = "unknown" if stage == "data" else "retry"
+        detail = "Mail server acceptance is unknown; check its logs before taking further action." if state == "unknown" else "Could not reach or finish connecting to the mail server."
+        raise DeliveryError(state, detail) from exc
+    finally:
+        if smtp:
+            # A failed QUIT after a 250 DATA response must not turn an accepted email into a retry.
+            with suppress(Exception):
+                smtp.quit()
+            with suppress(Exception):
+                smtp.close()
+
+
+def message_id(delivery_id: str, public_url: str) -> str:
+    host = urlsplit(public_url).hostname or "magent.local"
+    return f"<magent-recap-{delivery_id}@{host}>"

backend/app/services/recap_store.py

@@ -0,0 +1,235 @@
+"""Durable consent, schedule and delivery records for personal email recaps."""
+
+import hashlib
+import secrets
+import sqlite3
+import uuid
+from contextlib import closing, contextmanager
+from datetime import datetime
+
+from .. import db
+from .monthly_reports import shift_month
+
+
+def init_schema(conn: sqlite3.Connection) -> None:
+    for statement in (
+        """CREATE TABLE IF NOT EXISTS email_recap_settings (
+            id INTEGER PRIMARY KEY CHECK (id = 1), enabled INTEGER NOT NULL DEFAULT 0,
+            day INTEGER NOT NULL DEFAULT 2, hour INTEGER NOT NULL DEFAULT 9,
+            public_url TEXT NOT NULL DEFAULT '', next_send_at REAL)""",
+        "INSERT OR IGNORE INTO email_recap_settings (id) VALUES (1)",
+        """CREATE TABLE IF NOT EXISTS email_recap_subscriptions (
+            user_id INTEGER PRIMARY KEY, state TEXT NOT NULL, email TEXT NOT NULL,
+            identity_source TEXT NOT NULL, identity_id TEXT NOT NULL, version TEXT NOT NULL,
+            confirmation_hash TEXT UNIQUE, confirmation_expires REAL, requested_at REAL NOT NULL,
+            confirmed_at REAL, unsubscribe_token TEXT NOT NULL UNIQUE)""",
+        """CREATE TABLE IF NOT EXISTS email_recap_deliveries (
+            id TEXT PRIMARY KEY, dedupe_key TEXT NOT NULL UNIQUE, user_id INTEGER NOT NULL,
+            month TEXT NOT NULL, kind TEXT NOT NULL, email TEXT NOT NULL,
+            subscription_version TEXT NOT NULL, public_url TEXT NOT NULL,
+            state TEXT NOT NULL DEFAULT 'queued', attempts INTEGER NOT NULL DEFAULT 0,
+            created_at REAL NOT NULL, updated_at REAL NOT NULL, next_attempt_at REAL NOT NULL,
+            claim TEXT, lease_until REAL, detail TEXT NOT NULL DEFAULT '')""",
+        "CREATE INDEX IF NOT EXISTS idx_email_recap_queue ON email_recap_deliveries (state, next_attempt_at)",
+        """CREATE TRIGGER IF NOT EXISTS email_recap_account_changed AFTER UPDATE OF email, is_blocked ON users
+            WHEN LOWER(TRIM(COALESCE(NEW.email, ''))) != LOWER(TRIM(COALESCE(OLD.email, '')))
+                OR NEW.is_blocked = 1
+            BEGIN UPDATE email_recap_subscriptions SET state = 'off', confirmation_hash = NULL,
+                confirmed_at = NULL WHERE user_id = NEW.id; END""",
+        """CREATE TRIGGER IF NOT EXISTS email_recap_account_deleted AFTER DELETE ON users
+            BEGIN DELETE FROM email_recap_subscriptions WHERE user_id = OLD.id;
+            UPDATE email_recap_deliveries SET state = 'cancelled', detail = 'Account removed.'
+                WHERE user_id = OLD.id AND state IN ('queued', 'retry', 'preparing'); END""",
+        """CREATE TRIGGER IF NOT EXISTS email_recap_identity_changed AFTER UPDATE ON jellyfin_user_links
+            WHEN NEW.jellyfin_user_id != OLD.jellyfin_user_id OR NEW.source != OLD.source
+                OR NEW.local_user_id != OLD.local_user_id
+            BEGIN UPDATE email_recap_subscriptions SET state = 'off', confirmation_hash = NULL,
+                confirmed_at = NULL WHERE user_id = OLD.local_user_id; END""",
+        """CREATE TRIGGER IF NOT EXISTS email_recap_identity_deleted AFTER DELETE ON jellyfin_user_links
+            BEGIN UPDATE email_recap_subscriptions SET state = 'off', confirmation_hash = NULL,
+                confirmed_at = NULL WHERE user_id = OLD.local_user_id; END""",
+    ):
+        conn.execute(statement)
+
+
+@contextmanager
+def transaction():
+    with closing(db._connect()) as conn, conn:
+        conn.row_factory = sqlite3.Row
+        conn.execute("BEGIN IMMEDIATE")
+        yield conn
+
+
+def read_one(sql: str, args=()) -> dict | None:
+    with closing(db._connect()) as conn:
+        conn.row_factory = sqlite3.Row
+        row = conn.execute(sql, args).fetchone()
+        return dict(row) if row else None
+
+
+def settings() -> dict:
+    row = read_one("SELECT * FROM email_recap_settings WHERE id = 1")
+    return {key: (bool(value) if key == "enabled" else value) for key, value in row.items() if key != "id"}
+
+
+def next_due(now: datetime, day: int, hour: int) -> datetime:
+    due = shift_month(now, 0).replace(day=day, hour=hour)
+    return due if due > now else shift_month(now, 1).replace(day=day, hour=hour)
+
+
+def save_settings(values: dict, now: datetime) -> dict:
+    with transaction() as conn:
+        old = dict(conn.execute("SELECT * FROM email_recap_settings WHERE id = 1").fetchone())
+        changed = any(old[key] != values[key] for key in ("day", "hour", "public_url"))
+        due = old["next_send_at"]
+        if not values["enabled"]:
+            due = None
+        elif not old["enabled"] or changed:
+            due = next_due(now, values["day"], values["hour"]).timestamp()
+        conn.execute("UPDATE email_recap_settings SET enabled=?, day=?, hour=?, public_url=?, next_send_at=? WHERE id=1",
+                     (values["enabled"], values["day"], values["hour"], values["public_url"], due))
+        if not values["enabled"] or changed:
+            conn.execute("""UPDATE email_recap_deliveries SET state='cancelled', detail='Schedule paused or changed.', updated_at=?
+                WHERE kind='scheduled' AND state IN ('queued', 'retry', 'preparing')""", (now.timestamp(),))
+    return settings()
+
+
+def subscription(user_id: int) -> dict | None:
+    return read_one("SELECT * FROM email_recap_subscriptions WHERE user_id=?", (user_id,))
+
+
+def disable(user_id: int) -> None:
+    with transaction() as conn:
+        conn.execute("UPDATE email_recap_subscriptions SET state='off', confirmation_hash=NULL, confirmed_at=NULL WHERE user_id=?", (user_id,))
+        conn.execute("""UPDATE email_recap_deliveries SET state='cancelled', detail='Email recaps turned off.'
+            WHERE user_id=? AND state IN ('queued', 'retry', 'preparing')""", (user_id,))
+
+
+def request_confirmation(user: dict, source: str, identity: str, now: float) -> str:
+    token = secrets.token_urlsafe(32)
+    with transaction() as conn:
+        old = conn.execute("SELECT * FROM email_recap_subscriptions WHERE user_id=?", (user["id"],)).fetchone()
+        if old and old["requested_at"] > now - 300:
+            raise ValueError("Please wait five minutes before requesting another confirmation email.")
+        conn.execute("""INSERT INTO email_recap_subscriptions
+            (user_id, state, email, identity_source, identity_id, version, confirmation_hash,
+             confirmation_expires, requested_at, confirmed_at, unsubscribe_token)
+            VALUES (?, 'pending', ?, ?, ?, ?, ?, ?, ?, NULL, ?)
+            ON CONFLICT(user_id) DO UPDATE SET state='pending', email=excluded.email,
+                identity_source=excluded.identity_source, identity_id=excluded.identity_id, version=excluded.version,
+                confirmation_hash=excluded.confirmation_hash, confirmation_expires=excluded.confirmation_expires,
+                requested_at=excluded.requested_at, confirmed_at=NULL, unsubscribe_token=excluded.unsubscribe_token""",
+            (user["id"], user["email"].strip(), source, identity, uuid.uuid4().hex,
+             hashlib.sha256(token.encode()).hexdigest(), now + 86400, now, secrets.token_urlsafe(32)))
+    return token
+
+
+def token_subscription(token: str, action: str) -> dict | None:
+    if action == "confirm":
+        return read_one("SELECT * FROM email_recap_subscriptions WHERE confirmation_hash=?",
+                        (hashlib.sha256(token.encode()).hexdigest(),))
+    return read_one("SELECT * FROM email_recap_subscriptions WHERE unsubscribe_token=?", (token,))
+
+
+def confirm(sub: dict, now: float) -> bool:
+    with transaction() as conn:
+        # Recheck address and blocked state in the same transaction as the consent write.
+        result = conn.execute("""UPDATE email_recap_subscriptions SET state='enabled', confirmed_at=?, confirmation_hash=NULL
+            WHERE user_id=? AND version=? AND state='pending' AND confirmation_expires>?
+            AND EXISTS (SELECT 1 FROM users WHERE users.id=user_id AND is_blocked=0
+                AND LOWER(TRIM(users.email))=LOWER(TRIM(email_recap_subscriptions.email)))""",
+            (now, sub["user_id"], sub["version"], now))
+        return result.rowcount == 1
+
+
+def _enqueue(conn, sub: dict, month: str, kind: str, key: str, public_url: str, now: float) -> str:
+    delivery_id = uuid.uuid4().hex
+    conn.execute("""INSERT OR IGNORE INTO email_recap_deliveries
+        (id, dedupe_key, user_id, month, kind, email, subscription_version, public_url,
+         created_at, updated_at, next_attempt_at) VALUES (?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?)""",
+        (delivery_id, key, sub["user_id"], month, kind, sub["email"], sub["version"], public_url, now, now, now))
+    return conn.execute("SELECT id FROM email_recap_deliveries WHERE dedupe_key=?", (key,)).fetchone()[0]
+
+
+def enqueue_test(sub: dict, month: str, request_id: str, public_url: str, now: float) -> str:
+    key = f"test:{sub['user_id']}:{request_id}"
+    with transaction() as conn:
+        existing = conn.execute("SELECT id FROM email_recap_deliveries WHERE dedupe_key=?", (key,)).fetchone()
+        if existing:
+            return existing[0]
+        recent = conn.execute("SELECT 1 FROM email_recap_deliveries WHERE user_id=? AND kind='test' AND created_at>?",
+                              (sub["user_id"], now - 300)).fetchone()
+        if recent:
+            raise ValueError("Please wait five minutes between test emails.")
+        return _enqueue(conn, sub, month, "test", key, public_url, now)
+
+
+def enqueue_due(now: datetime) -> int:
+    with transaction() as conn:
+        config = dict(conn.execute("SELECT * FROM email_recap_settings WHERE id=1").fetchone())
+        if not config["enabled"] or not config["next_send_at"] or config["next_send_at"] > now.timestamp():
+            return 0
+        # After long downtime, send only the latest due recap; never backfill a pile of old emails.
+        due = shift_month(now, 0).replace(day=config["day"], hour=config["hour"])
+        if due > now:
+            due = shift_month(now, -1).replace(day=config["day"], hour=config["hour"])
+        month = shift_month(due, -1).strftime("%Y-%m")
+        subs = conn.execute("SELECT * FROM email_recap_subscriptions WHERE state='enabled' AND confirmed_at<=?", (due.timestamp(),)).fetchall()
+        before = conn.total_changes
+        for sub in subs:
+            _enqueue(conn, dict(sub), month, "scheduled", f"scheduled:{sub['user_id']}:{month}", config["public_url"], now.timestamp())
+        count = conn.total_changes - before
+        conn.execute("UPDATE email_recap_settings SET next_send_at=? WHERE id=1",
+                     (next_due(now, config["day"], config["hour"]).timestamp(),))
+        return count
+
+
+def claim_delivery(now: float) -> dict | None:
+    with transaction() as conn:
+        # A crashed worker could already have handed DATA to SMTP. Do not resend it automatically.
+        conn.execute("""UPDATE email_recap_deliveries SET state='unknown', detail='Delivery interrupted after sending began; check the mail server.', updated_at=?
+            WHERE state='sending' AND lease_until<?""", (now, now))
+        conn.execute("""UPDATE email_recap_deliveries SET state=CASE WHEN attempts>=3 THEN 'failed' ELSE 'retry' END,
+            next_attempt_at=?, updated_at=?, detail='Report preparation interrupted.'
+            WHERE state='preparing' AND lease_until<?""", (now, now, now))
+        row = conn.execute("""SELECT * FROM email_recap_deliveries WHERE state IN ('queued', 'retry') AND next_attempt_at<=?
+            ORDER BY created_at, id LIMIT 1""", (now,)).fetchone()
+        if not row:
+            return None
+        claim = uuid.uuid4().hex
+        conn.execute("""UPDATE email_recap_deliveries SET state='preparing', claim=?, lease_until=?,
+            attempts=attempts+1, updated_at=? WHERE id=?""", (claim, now + 1800, now, row["id"]))
+        return dict(conn.execute("SELECT * FROM email_recap_deliveries WHERE id=?", (row["id"],)).fetchone())
+
+
+def begin_sending(delivery: dict, now: float) -> bool:
+    with transaction() as conn:
+        # Consent may have changed while the report or SMTP connection was being prepared.
+        result = conn.execute("""UPDATE email_recap_deliveries SET state='sending', updated_at=?, lease_until=?
+            WHERE id=? AND claim=? AND state='preparing'
+            AND EXISTS (SELECT 1 FROM email_recap_subscriptions s JOIN users u ON u.id=s.user_id
+                JOIN jellyfin_user_links j ON j.local_user_id=u.id AND j.source=s.identity_source
+                WHERE s.user_id=email_recap_deliveries.user_id AND s.state='enabled'
+                AND s.version=email_recap_deliveries.subscription_version AND u.is_blocked=0
+                AND LOWER(TRIM(u.email))=LOWER(TRIM(s.email)) AND j.jellyfin_user_id=s.identity_id)
+            AND EXISTS (SELECT 1 FROM email_recap_settings c WHERE c.id=1 AND c.public_url=email_recap_deliveries.public_url
+                AND (email_recap_deliveries.kind='test' OR c.enabled=1))""", (now, now + 1800, delivery["id"], delivery["claim"]))
+        return result.rowcount == 1
+
+
+def finish(delivery: dict, state: str, detail: str, now: float, delay: int = 0) -> None:
+    with transaction() as conn:
+        conn.execute("""UPDATE email_recap_deliveries SET state=?, detail=?, updated_at=?, next_attempt_at=?, lease_until=NULL
+            WHERE id=? AND claim=? AND state IN ('preparing', 'sending')""",
+            (state, detail, now, now + delay, delivery["id"], delivery["claim"]))
+
+
+def history(limit: int = 50, offset: int = 0) -> dict:
+    with closing(db._connect()) as conn:
+        conn.row_factory = sqlite3.Row
+        rows = conn.execute("""SELECT d.id, d.month, d.kind, d.email, d.state, d.attempts, d.created_at, d.updated_at,
+            d.next_attempt_at, d.detail, u.username FROM email_recap_deliveries d LEFT JOIN users u ON u.id=d.user_id
+            ORDER BY d.created_at DESC, d.id LIMIT ? OFFSET ?""", (limit, offset)).fetchall()
+        total = conn.execute("SELECT COUNT(*) FROM email_recap_deliveries").fetchone()[0]
+        subscribers = conn.execute("SELECT COUNT(*) FROM email_recap_subscriptions WHERE state='enabled'").fetchone()[0]
+    return {"deliveries": [dict(row) for row in rows], "total": total, "subscribers": subscribers}