Add account self-delete and subscription lifecycle sync (#34) (#39)

## Summary
- Closes [#34](#34)
- Companion for [chat_web_app#75](ai_ml_operations/chat_web_app#75) (portal cancel/change local sync)
- Soft-delete `DELETE /api/user/` for the authenticated user only: `deleted=True`, `is_active=False`, hide conversations, blacklist outstanding refresh tokens; staff self-delete rejected
- Stripe `customer.subscription.updated` / `deleted` webhooks sync plan status, `cancel_at_period_end`, and `current_period_end`; checkout assigns plan from `metadata.plan_slug`
- **UserAuthEvent audit**: `account_deleted`, `subscription_started` (first active plan), `subscription_updated` (plan/status/cancel changes) — visible on user admin
- Document FE contract in README (endpoint, response, post-delete logout)

## Test plan
- [ ] `uv run python manage.py test chat_backend.tests.test_views_users.CustomUserSelfDeleteTestCase finance.tests`
- [ ] Authenticated `DELETE /api/user/` soft-deletes self, hides conversations, blocks re-login, writes `account_deleted` auth event
- [ ] Checkout / Backer assign writes `subscription_started`; portal cancel/change writes `subscription_updated`
- [ ] Anonymous / staff self-delete rejected; body cannot target another user
- [ ] After portal cancel, webhook sets `cancel_at_period_end` / `canceled` on `GET /finance/subscription/`Reviewed-on: #39

llm_be/chat_backend/migrations/0027_user_auth_event_subscription_and_delete.py

@@ -0,0 +1,28 @@
+# Generated by Django 6.0 on 2026-08-01 19:21
+
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ("chat_backend", "0026_oauthidentity"),
+    ]
+
+    operations = [
+        migrations.AlterField(
+            model_name="userauthevent",
+            name="event_type",
+            field=models.CharField(
+                choices=[
+                    ("password_reset_requested", "Password reset requested"),
+                    ("password_set", "Password set"),
+                    ("invite_sent", "Invite sent"),
+                    ("account_deleted", "Account deleted"),
+                    ("subscription_started", "Subscription started"),
+                    ("subscription_updated", "Subscription updated"),
+                ],
+                max_length=64,
+            ),
+        ),
+    ]

llm_be/chat_backend/models.py

@@ -82,7 +82,7 @@ class CustomUser(AbstractUser):
 
 
 class UserAuthEvent(models.Model):
-    """Audit trail for password reset / set actions, shown on user admin."""
+    """Audit trail for auth / account / subscription actions (user admin)."""
 
     class EventType(models.TextChoices):
         PASSWORD_RESET_REQUESTED = (
@@ -91,6 +91,9 @@ class UserAuthEvent(models.Model):
         )
         PASSWORD_SET = ("password_set", "Password set")
         INVITE_SENT = ("invite_sent", "Invite sent")
+        ACCOUNT_DELETED = ("account_deleted", "Account deleted")
+        SUBSCRIPTION_STARTED = ("subscription_started", "Subscription started")
+        SUBSCRIPTION_UPDATED = ("subscription_updated", "Subscription updated")
 
     user = models.ForeignKey(
         CustomUser,

llm_be/chat_backend/serializers.py

@@ -26,6 +26,17 @@ class MyTokenObtainPairSerializer(TokenObtainPairSerializer):
 
         return token
 
+    def validate(self, attrs):
+        data = super().validate(attrs)
+        if getattr(self.user, "deleted", False):
+            from rest_framework_simplejwt.exceptions import AuthenticationFailed
+
+            raise AuthenticationFailed(
+                "No active account found with the given credentials",
+                code="no_active_account",
+            )
+        return data
+
 
 class CompanySerializer(serializers.ModelSerializer):
     class Meta:
@@ -70,12 +81,18 @@ class CustomUserSerializer(serializers.ModelSerializer):
                 "status": UserSubscription.Status.NONE,
                 "source": UserSubscription.Source.NONE,
                 "needs_checkout": True,
+                "cancel_at_period_end": False,
+                "current_period_end": None,
             }
         return {
             "plan": plan_to_dict(sub.plan) if sub.plan_id else None,
             "status": sub.status,
             "source": sub.source,
             "needs_checkout": needs_checkout(obj),
+            "cancel_at_period_end": bool(sub.cancel_at_period_end),
+            "current_period_end": (
+                sub.current_period_end.isoformat() if sub.current_period_end else None
+            ),
         }
 
 

llm_be/chat_backend/services/account_deletion.py

@@ -0,0 +1,92 @@
+"""Self-service account soft-delete helpers (#34)."""
+
+from __future__ import annotations
+
+import logging
+
+from django.db import transaction
+from rest_framework_simplejwt.token_blacklist.models import (
+    BlacklistedToken,
+    OutstandingToken,
+)
+from rest_framework_simplejwt.tokens import RefreshToken
+
+from chat_backend.models import Conversation, CustomUser, UserAuthEvent
+
+logger = logging.getLogger(__name__)
+
+
+class AccountDeletionError(Exception):
+    """Raised when self-delete is not allowed for the requesting user."""
+
+    def __init__(self, detail: str, *, code: str = "delete_forbidden"):
+        super().__init__(detail)
+        self.detail = detail
+        self.code = code
+
+
+def _blacklist_outstanding_tokens(user: CustomUser) -> int:
+    """Blacklist all outstanding refresh tokens for the user. Returns count."""
+    count = 0
+    for outstanding in OutstandingToken.objects.filter(user=user):
+        _token, created = BlacklistedToken.objects.get_or_create(token=outstanding)
+        if created:
+            count += 1
+    return count
+
+
+def _blacklist_refresh_token(refresh_token: str | None) -> None:
+    if not refresh_token:
+        return
+    try:
+        RefreshToken(refresh_token).blacklist()
+    except Exception:
+        logger.info("Self-delete: optional refresh token could not be blacklisted")
+
+
+@transaction.atomic
+def soft_delete_account(
+    user: CustomUser,
+    *,
+    refresh_token: str | None = None,
+    ip_address: str | None = None,
+) -> CustomUser:
+    """
+    Soft-delete the requesting user and hide their conversations.
+
+    Privacy (v1): personal data is retained under soft-delete for admin/audit.
+    Full purge (chats, documents, RAG vectors, auth events) is a follow-up.
+    """
+    if user.is_staff or user.is_superuser:
+        raise AccountDeletionError(
+            "Staff accounts cannot self-delete. Contact an administrator.",
+            code="staff_forbidden",
+        )
+
+    if user.deleted:
+        raise AccountDeletionError(
+            "This account has already been deleted.",
+            code="already_deleted",
+        )
+
+    user.deleted = True
+    user.is_active = False
+    user.save(update_fields=["deleted", "is_active"])
+
+    Conversation.objects.filter(user=user, deleted=False).update(deleted=True)
+
+    UserAuthEvent.log(
+        user,
+        UserAuthEvent.EventType.ACCOUNT_DELETED,
+        detail="Self-service account soft-delete",
+        ip_address=ip_address,
+    )
+
+    _blacklist_refresh_token(refresh_token)
+    blacklisted = _blacklist_outstanding_tokens(user)
+    logger.info(
+        "Soft-deleted user pk=%s; blacklisted_outstanding=%s",
+        user.pk,
+        blacklisted,
+    )
+    return user

llm_be/chat_backend/tests/test_views_users.py

@@ -7,13 +7,18 @@ from rest_framework_simplejwt.tokens import RefreshToken
 
 from chat_backend.models import (
     Announcement,
+    Conversation,
     CustomUser,
     Feedback,
     OutboundEmail,
     UserAuthEvent,
 )
+from rest_framework_simplejwt.token_blacklist.models import (
+    BlacklistedToken,
+    OutstandingToken,
+)
 
-from .factories import make_company, make_user
+from .factories import make_company, make_conversation, make_user
 
 
 class AuthenticationRequiredTestCase(APITestCase):
@@ -520,3 +525,102 @@ class CustomUserGetTestCase(APITestCase):
         self.assertEqual(response.data["email"], user.email)
         self.assertEqual(response.data["company"]["name"], "Globex")
         self.assertNotIn("password", response.data)
+
+
+class CustomUserSelfDeleteTestCase(APITestCase):
+    def setUp(self):
+        self.company = make_company("Acme")
+        self.user = make_user(
+            email="deleteme@example.com",
+            password="testpass123",
+            company=self.company,
+        )
+        self.url = reverse("delete_user")
+
+    def test_unauthenticated_rejected(self):
+        response = self.client.delete(self.url)
+        self.assertEqual(response.status_code, status.HTTP_401_UNAUTHORIZED)
+
+    def test_soft_deletes_self_and_hides_conversations(self):
+        conversation = make_conversation(user=self.user, title="Keep hidden")
+        refresh = RefreshToken.for_user(self.user)
+        self.client.force_authenticate(user=self.user)
+
+        response = self.client.delete(
+            self.url, {"refresh_token": str(refresh)}, format="json"
+        )
+
+        self.assertEqual(response.status_code, status.HTTP_200_OK)
+        self.assertTrue(response.data["deleted"])
+
+        self.user.refresh_from_db()
+        self.assertTrue(self.user.deleted)
+        self.assertFalse(self.user.is_active)
+        delete_event = UserAuthEvent.objects.get(
+            user=self.user,
+            event_type=UserAuthEvent.EventType.ACCOUNT_DELETED,
+        )
+        self.assertIn("soft-delete", delete_event.detail.lower())
+        self.assertTrue(
+            CustomUser.objects.filter(pk=self.user.pk, deleted=True).exists()
+        )
+
+        conversation.refresh_from_db()
+        self.assertTrue(conversation.deleted)
+
+        outstanding = OutstandingToken.objects.filter(user=self.user)
+        self.assertTrue(outstanding.exists())
+        for token in outstanding:
+            self.assertTrue(BlacklistedToken.objects.filter(token=token).exists())
+
+        # Soft-deleted users cannot obtain new tokens.
+        login = self.client.post(
+            reverse("token_create"),
+            {"username": self.user.username, "password": "testpass123"},
+            format="json",
+        )
+        self.assertEqual(login.status_code, status.HTTP_401_UNAUTHORIZED)
+
+        # Conversations list hides soft-deleted rows for any remaining session.
+        other = make_user(email="alive@example.com", company=self.company)
+        make_conversation(user=other, title="Still visible")
+        self.client.force_authenticate(user=other)
+        listed = self.client.get(reverse("conversations"))
+        titles = [row["title"] for row in listed.data]
+        self.assertNotIn("Keep hidden", titles)
+
+    def test_cannot_delete_another_user_via_body(self):
+        """Endpoint always targets request.user; body email/id is ignored."""
+        other = make_user(email="other@example.com", company=self.company)
+        make_conversation(user=other, title="Other chat")
+        self.client.force_authenticate(user=self.user)
+
+        response = self.client.delete(
+            self.url,
+            {"email": other.email, "user_id": other.pk},
+            format="json",
+        )
+
+        self.assertEqual(response.status_code, status.HTTP_200_OK)
+        self.user.refresh_from_db()
+        other.refresh_from_db()
+        self.assertTrue(self.user.deleted)
+        self.assertFalse(other.deleted)
+        self.assertFalse(
+            Conversation.objects.filter(user=other, deleted=True).exists()
+        )
+
+    def test_staff_cannot_self_delete(self):
+        staff = make_user(
+            email="staff@example.com",
+            company=self.company,
+            is_staff=True,
+        )
+        self.client.force_authenticate(user=staff)
+
+        response = self.client.delete(self.url, format="json")
+
+        self.assertEqual(response.status_code, status.HTTP_400_BAD_REQUEST)
+        self.assertEqual(response.data["code"], "staff_forbidden")
+        staff.refresh_from_db()
+        self.assertFalse(staff.deleted)

llm_be/chat_backend/urls.py

@@ -5,6 +5,7 @@ from .views import (
     CustomObtainTokenView,
     CustomUserCreate,
     CustomUserInvite,
+    CustomUserSelfDeleteView,
     LogoutAndBlacklistRefreshTokenForUserView,
     CustomUserGet,
     PublicSettingsView,
@@ -57,6 +58,7 @@ urlpatterns = [
         name="blacklist",
     ),
     path("user/get/", CustomUserGet.as_view(), name="get_user"),
+    path("user/", CustomUserSelfDeleteView.as_view(), name="delete_user"),
     path(
         "user/acknowledge_tos/",
         AcknowledgeTermsOfService.as_view(),

llm_be/chat_backend/views.py

@@ -305,6 +305,48 @@ class CustomUserGet(APIView):
             return Response({}, status=status.HTTP_400_BAD_REQUEST)
 
 
+class CustomUserSelfDeleteView(APIView):
+    """
+    Soft-delete the authenticated user's own account (#34).
+
+    Frontend contract:
+    - Method/path: ``DELETE /api/user/``
+    - Optional body: ``{"refresh_token": "<current refresh>"}`` to blacklist
+      the active session immediately (outstanding tokens are also blacklisted).
+    - Success: ``200`` with ``{"detail": "Account deleted.", "deleted": true}``
+    - After success: clear local tokens, redirect to sign-in. Subsequent
+      ``/token/obtain/`` and authenticated calls fail (``is_active=False``,
+      ``deleted=True``).
+    - Privacy v1: soft-delete only (no anonymization / hard purge).
+    """
+
+    http_method_names = ["delete", "head", "options"]
+
+    def delete(self, request, format="json"):
+        from chat_backend.services.account_deletion import (
+            AccountDeletionError,
+            soft_delete_account,
+        )
+
+        refresh_token = request.data.get("refresh_token")
+        try:
+            soft_delete_account(
+                request.user,
+                refresh_token=refresh_token,
+                ip_address=_client_ip(request),
+            )
+        except AccountDeletionError as exc:
+            return Response(
+                {"detail": exc.detail, "code": exc.code},
+                status=status.HTTP_400_BAD_REQUEST,
+            )
+
+        return Response(
+            {"detail": "Account deleted.", "deleted": True},
+            status=status.HTTP_200_OK,
+        )
+
+
 class FeedbackView(APIView):
     http_method_names = ["post", "get"]
 

llm_be/finance/migrations/0003_subscription_cancel_period_fields.py

@@ -0,0 +1,30 @@
+# Generated by Django 6.0 on 2026-08-01 19:11
+
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ("finance", "0002_subscription_plans_quotas"),
+    ]
+
+    operations = [
+        migrations.AddField(
+            model_name="usersubscription",
+            name="cancel_at_period_end",
+            field=models.BooleanField(
+                default=False,
+                help_text="Stripe: subscription will cancel at current_period_end.",
+            ),
+        ),
+        migrations.AddField(
+            model_name="usersubscription",
+            name="current_period_end",
+            field=models.DateTimeField(
+                blank=True,
+                help_text="Stripe billing period end (access remains until then when canceling).",
+                null=True,
+            ),
+        ),
+    ]

llm_be/finance/models.py

@@ -149,6 +149,15 @@ class UserSubscription(TimeInfoBase):
         default="",
         db_index=True,
     )
+    cancel_at_period_end = models.BooleanField(
+        default=False,
+        help_text="Stripe: subscription will cancel at current_period_end.",
+    )
+    current_period_end = models.DateTimeField(
+        null=True,
+        blank=True,
+        help_text="Stripe billing period end (access remains until then when canceling).",
+    )
     monthly_token_quota_override = models.PositiveIntegerField(
         null=True,
         blank=True,

llm_be/finance/services/plans.py

@@ -8,10 +8,25 @@ from typing import Any
 from django.db import transaction
 from django.utils import timezone
 
+from chat_backend.models import UserAuthEvent
 from finance.models import BackerEmail, SubscriptionPlan, UserSubscription
 
 logger = logging.getLogger(__name__)
 
+
+def log_subscription_auth_event(
+    user,
+    *,
+    started: bool,
+    detail: str,
+) -> None:
+    event_type = (
+        UserAuthEvent.EventType.SUBSCRIPTION_STARTED
+        if started
+        else UserAuthEvent.EventType.SUBSCRIPTION_UPDATED
+    )
+    UserAuthEvent.log(user, event_type, detail=detail[:512])
+
 # Seed catalog for #36. Standard/Pro/Business stay hidden until explicitly enabled.
 PLAN_SEED: list[dict[str, Any]] = [
     {
@@ -141,14 +156,63 @@ def assign_plan(
     source: str,
     status: str = UserSubscription.Status.ACTIVE,
     stripe_subscription_id: str = "",
+    log_auth_event: bool = True,
 ) -> UserSubscription:
     sub = get_or_create_user_subscription(user)
+    prev_plan_id = sub.plan_id
+    prev_status = sub.status
+    prev_source = sub.source
+    prev_stripe_sub = sub.stripe_subscription_id or ""
+    had_active = (
+        prev_status == UserSubscription.Status.ACTIVE and prev_plan_id is not None
+    )
+
     sub.plan = plan
     sub.source = source
     sub.status = status
     if stripe_subscription_id:
         sub.stripe_subscription_id = stripe_subscription_id
     sub.save()
+
+    if log_auth_event:
+        became_active = (
+            status == UserSubscription.Status.ACTIVE and plan is not None
+        )
+        changed = (
+            prev_plan_id != sub.plan_id
+            or prev_status != sub.status
+            or prev_source != sub.source
+            or (
+                bool(stripe_subscription_id)
+                and prev_stripe_sub != (sub.stripe_subscription_id or "")
+            )
+        )
+        if became_active and not had_active:
+            log_subscription_auth_event(
+                user,
+                started=True,
+                detail=(
+                    f"plan={plan.slug} source={source} status={status}"
+                    + (
+                        f" stripe_subscription_id={stripe_subscription_id}"
+                        if stripe_subscription_id
+                        else ""
+                    )
+                ),
+            )
+        elif changed:
+            log_subscription_auth_event(
+                user,
+                started=False,
+                detail=(
+                    f"plan={plan.slug} source={source} status={status}"
+                    + (
+                        f" stripe_subscription_id={stripe_subscription_id}"
+                        if stripe_subscription_id
+                        else ""
+                    )
+                ),
+            )
     return sub
 
 
@@ -221,17 +285,119 @@ def assign_founders_from_stripe(
     *,
     stripe_subscription_id: str = "",
 ) -> UserSubscription:
+    """Backward-compatible helper; prefer ``assign_plan_from_stripe``."""
+    return assign_plan_from_stripe(
+        user,
+        plan_slug=SubscriptionPlan.Slug.FOUNDERS,
+        stripe_subscription_id=stripe_subscription_id,
+    )
+
+
+def assign_plan_from_stripe(
+    user,
+    *,
+    plan_slug: str | None = None,
+    stripe_subscription_id: str = "",
+    status: str = UserSubscription.Status.ACTIVE,
+    cancel_at_period_end: bool | None = None,
+    current_period_end=None,
+    keep_existing_plan_if_unknown: bool = False,
+) -> UserSubscription:
+    """Assign a catalog plan from a Stripe Checkout / subscription event."""
     seed_subscription_plans(update_existing=False)
-    plan = get_plan(SubscriptionPlan.Slug.FOUNDERS)
+    existing = (
+        UserSubscription.objects.filter(user=user).select_related("plan").first()
+    )
+    prev_cancel = bool(existing.cancel_at_period_end) if existing else False
+    prev_period_end = existing.current_period_end if existing else None
+    had_active = bool(
+        existing
+        and existing.status == UserSubscription.Status.ACTIVE
+        and existing.plan_id
+    )
+
+    slug = (plan_slug or "").strip().lower()
+    plan = get_plan(slug) if slug else None
+    if plan is None and keep_existing_plan_if_unknown and existing and existing.plan_id:
+        plan = existing.plan
+    if plan is None:
+        if slug:
+            logger.warning(
+                "Unknown plan_slug=%s; falling back to Founders for user=%s",
+                slug,
+                getattr(user, "pk", None),
+            )
+        plan = get_plan(SubscriptionPlan.Slug.FOUNDERS)
     if plan is None:
         raise RuntimeError("Founders plan missing from catalog")
-    return assign_plan(
+
+    # Single auth-event log after plan + cancel fields are applied.
+    sub = assign_plan(
         user,
         plan=plan,
         source=UserSubscription.Source.STRIPE,
-        status=UserSubscription.Status.ACTIVE,
+        status=status,
         stripe_subscription_id=stripe_subscription_id or "",
+        log_auth_event=False,
     )
+    update_fields: list[str] = []
+    if cancel_at_period_end is not None:
+        sub.cancel_at_period_end = bool(cancel_at_period_end)
+        update_fields.append("cancel_at_period_end")
+    if current_period_end is not None:
+        sub.current_period_end = current_period_end
+        update_fields.append("current_period_end")
+    if update_fields:
+        sub.save(update_fields=update_fields)
+
+    became_active = (
+        sub.status == UserSubscription.Status.ACTIVE and sub.plan_id is not None
+    )
+    cancel_changed = (
+        cancel_at_period_end is not None
+        and bool(cancel_at_period_end) != prev_cancel
+    )
+    period_changed = (
+        current_period_end is not None and current_period_end != prev_period_end
+    )
+    plan_or_status_changed = (
+        not existing
+        or existing.plan_id != sub.plan_id
+        or existing.status != sub.status
+        or (existing.source != sub.source)
+        or (
+            bool(stripe_subscription_id)
+            and (existing.stripe_subscription_id or "")
+            != (sub.stripe_subscription_id or "")
+        )
+    )
+    if became_active and not had_active:
+        log_subscription_auth_event(
+            user,
+            started=True,
+            detail=(
+                f"plan={sub.plan.slug} source={sub.source} status={sub.status}"
+                f" cancel_at_period_end={sub.cancel_at_period_end}"
+            ),
+        )
+    elif plan_or_status_changed or cancel_changed or period_changed:
+        log_subscription_auth_event(
+            user,
+            started=False,
+            detail=(
+                f"plan={sub.plan.slug if sub.plan_id else 'none'} "
+                f"source={sub.source} status={sub.status} "
+                f"cancel_at_period_end={sub.cancel_at_period_end}"
+            ),
+        )
+    return sub
+
+
+def resolve_plan_from_stripe_price(price_id: str | None) -> SubscriptionPlan | None:
+    """Map a Stripe Price id to a local SubscriptionPlan when configured."""
+    if not price_id:
+        return None
+    return SubscriptionPlan.objects.filter(stripe_price_id=price_id).first()
 
 
 def plan_to_dict(plan: SubscriptionPlan | None) -> dict[str, Any] | None:

llm_be/finance/services/webhooks.py

@@ -10,13 +10,68 @@ from django.contrib.auth import get_user_model
 from django.db import transaction
 from django.utils import timezone
 
-from finance.models import Invoice, Payment
-from finance.services.plans import assign_founders_from_stripe
+from finance.models import Invoice, Payment, UserSubscription
+from finance.services.plans import (
+    assign_plan_from_stripe,
+    get_or_create_user_subscription,
+    log_subscription_auth_event,
+    resolve_plan_from_stripe_price,
+)
 
 logger = logging.getLogger(__name__)
 User = get_user_model()
 
 
+def _stripe_status_to_local(stripe_status: str | None) -> str:
+    mapping = {
+        "active": UserSubscription.Status.ACTIVE,
+        "trialing": UserSubscription.Status.ACTIVE,
+        "past_due": UserSubscription.Status.PAST_DUE,
+        "unpaid": UserSubscription.Status.PAST_DUE,
+        "canceled": UserSubscription.Status.CANCELED,
+        "incomplete_expired": UserSubscription.Status.CANCELED,
+    }
+    return mapping.get((stripe_status or "").lower(), UserSubscription.Status.NONE)
+
+
+def _plan_slug_from_subscription(subscription: dict[str, Any]) -> str | None:
+    metadata = subscription.get("metadata") or {}
+    if metadata.get("plan_slug"):
+        return metadata.get("plan_slug")
+    items = (subscription.get("items") or {}).get("data") or []
+    if not items:
+        return None
+    price = (items[0] or {}).get("price") or {}
+    price_id = price.get("id") if isinstance(price, dict) else None
+    plan = resolve_plan_from_stripe_price(price_id)
+    return plan.slug if plan else None
+
+
+def _user_from_subscription(subscription: dict[str, Any]):
+    metadata = subscription.get("metadata") or {}
+    user = _user_from_metadata(metadata)
+    if user is not None:
+        return user
+    sub_id = subscription.get("id")
+    if sub_id:
+        existing = (
+            Invoice.objects.filter(stripe_subscription_id=sub_id)
+            .select_related("user")
+            .order_by("-created")
+            .first()
+        )
+        if existing:
+            return existing.user
+        local_sub = (
+            UserSubscription.objects.filter(stripe_subscription_id=sub_id)
+            .select_related("user")
+            .first()
+        )
+        if local_sub:
+            return local_sub.user
+    return None
+
+
 def _ts_to_dt(value: int | None):
     if not value:
         return None
@@ -213,8 +268,9 @@ def handle_checkout_session_completed(session: dict[str, Any]) -> Invoice | None
             paid_at=timezone.now(),
         )
     if session.get("payment_status") == "paid" or session.get("subscription"):
-        assign_founders_from_stripe(
+        assign_plan_from_stripe(
             user,
+            plan_slug=metadata.get("plan_slug"),
             stripe_subscription_id=session.get("subscription") or "",
         )
     return invoice
@@ -276,8 +332,9 @@ def handle_invoice_paid(stripe_invoice: dict[str, Any]) -> Invoice | None:
             stripe_charge_id=charge if isinstance(charge, str) else None,
             paid_at=paid_at,
         )
-    assign_founders_from_stripe(
+    assign_plan_from_stripe(
         user,
+        plan_slug=metadata.get("plan_slug"),
         stripe_subscription_id=stripe_invoice.get("subscription") or "",
     )
     return invoice
@@ -326,6 +383,68 @@ def handle_invoice_payment_failed(stripe_invoice: dict[str, Any]) -> Invoice | N
     return invoice
 
 
+def handle_customer_subscription_updated(subscription: dict[str, Any]):
+    """Sync local UserSubscription after portal plan change / cancel schedule."""
+    user = _user_from_subscription(subscription)
+    if user is None:
+        logger.error(
+            "customer.subscription.updated: cannot resolve user for %s",
+            subscription.get("id"),
+        )
+        return None
+
+    local_status = _stripe_status_to_local(subscription.get("status"))
+    if subscription.get("cancel_at_period_end") and local_status == (
+        UserSubscription.Status.ACTIVE
+    ):
+        # Still active until period end; keep ACTIVE and surface cancel flag.
+        pass
+
+    return assign_plan_from_stripe(
+        user,
+        plan_slug=_plan_slug_from_subscription(subscription),
+        stripe_subscription_id=subscription.get("id") or "",
+        status=local_status or UserSubscription.Status.ACTIVE,
+        cancel_at_period_end=bool(subscription.get("cancel_at_period_end")),
+        current_period_end=_ts_to_dt(subscription.get("current_period_end")),
+        keep_existing_plan_if_unknown=True,
+    )
+
+
+def handle_customer_subscription_deleted(subscription: dict[str, Any]):
+    """Mark local subscription canceled when Stripe subscription ends."""
+    user = _user_from_subscription(subscription)
+    if user is None:
+        logger.error(
+            "customer.subscription.deleted: cannot resolve user for %s",
+            subscription.get("id"),
+        )
+        return None
+
+    sub = get_or_create_user_subscription(user)
+    prev_status = sub.status
+    sub.status = UserSubscription.Status.CANCELED
+    sub.cancel_at_period_end = False
+    sub.current_period_end = _ts_to_dt(subscription.get("current_period_end"))
+    if subscription.get("id"):
+        sub.stripe_subscription_id = subscription["id"]
+    # Preserve plan so UI can show what ended; source stays stripe.
+    if sub.source == UserSubscription.Source.NONE:
+        sub.source = UserSubscription.Source.STRIPE
+    sub.save()
+    if prev_status != UserSubscription.Status.CANCELED:
+        log_subscription_auth_event(
+            user,
+            started=False,
+            detail=(
+                f"plan={sub.plan.slug if sub.plan_id else 'none'} "
+                f"source={sub.source} status={sub.status} "
+                f"stripe_subscription_id={sub.stripe_subscription_id}"
+            ),
+        )
+    return sub
+
+
 def dispatch_stripe_event(event: dict[str, Any]):
     """Route a verified Stripe event to the appropriate handler."""
     event_type = event.get("type")
@@ -337,6 +456,10 @@ def dispatch_stripe_event(event: dict[str, Any]):
         return handle_invoice_paid(data_object)
     if event_type == "invoice.payment_failed":
         return handle_invoice_payment_failed(data_object)
+    if event_type == "customer.subscription.updated":
+        return handle_customer_subscription_updated(data_object)
+    if event_type == "customer.subscription.deleted":
+        return handle_customer_subscription_deleted(data_object)
 
     logger.info("Ignoring unhandled Stripe event type: %s", event_type)
     return None

llm_be/finance/tests/test_webhooks.py

@@ -8,10 +8,14 @@ from rest_framework import status
 from rest_framework.test import APITestCase
 
 from chat_backend.tests.factories import make_company, make_user
-from finance.models import Invoice, Payment
+from chat_backend.models import UserAuthEvent
+from finance.models import Invoice, Payment, UserSubscription
+from finance.services.plans import assign_plan_from_stripe, seed_subscription_plans
 from finance.services.webhooks import (
     dispatch_stripe_event,
     handle_checkout_session_completed,
+    handle_customer_subscription_deleted,
+    handle_customer_subscription_updated,
     handle_invoice_paid,
     handle_invoice_payment_failed,
 )
@@ -107,6 +111,81 @@ class WebhookHandlerUnitTestCase(APITestCase):
         )
         self.assertIsNone(result)
 
+    def test_checkout_assigns_plan_from_metadata(self):
+        seed_subscription_plans(update_existing=False)
+        session = {
+            "id": "cs_test_plan_meta",
+            "metadata": {"user_id": str(self.user.pk), "plan_slug": "founders"},
+            "customer": "cus_meta",
+            "subscription": "sub_meta",
+            "payment_intent": "pi_meta",
+            "payment_status": "paid",
+            "amount_total": 1000,
+            "currency": "usd",
+        }
+        handle_checkout_session_completed(session)
+        sub = UserSubscription.objects.get(user=self.user)
+        self.assertEqual(sub.plan.slug, "founders")
+        self.assertEqual(sub.source, UserSubscription.Source.STRIPE)
+        self.assertEqual(sub.status, UserSubscription.Status.ACTIVE)
+        started = UserAuthEvent.objects.get(
+            user=self.user,
+            event_type=UserAuthEvent.EventType.SUBSCRIPTION_STARTED,
+        )
+        self.assertIn("founders", started.detail)
+
+    def test_subscription_updated_sets_cancel_at_period_end(self):
+        seed_subscription_plans(update_existing=False)
+        assign_plan_from_stripe(
+            self.user,
+            plan_slug="founders",
+            stripe_subscription_id="sub_cancel",
+        )
+        result = handle_customer_subscription_updated(
+            {
+                "id": "sub_cancel",
+                "status": "active",
+                "cancel_at_period_end": True,
+                "current_period_end": 1_700_259_200,
+                "metadata": {"user_id": str(self.user.pk), "plan_slug": "founders"},
+            }
+        )
+        self.assertIsNotNone(result)
+        sub = UserSubscription.objects.get(user=self.user)
+        self.assertTrue(sub.cancel_at_period_end)
+        self.assertEqual(sub.status, UserSubscription.Status.ACTIVE)
+        self.assertIsNotNone(sub.current_period_end)
+        updated = UserAuthEvent.objects.filter(
+            user=self.user,
+            event_type=UserAuthEvent.EventType.SUBSCRIPTION_UPDATED,
+        ).latest("created")
+        self.assertIn("cancel_at_period_end=True", updated.detail)
+
+    def test_subscription_deleted_marks_canceled(self):
+        seed_subscription_plans(update_existing=False)
+        assign_plan_from_stripe(
+            self.user,
+            plan_slug="founders",
+            stripe_subscription_id="sub_gone",
+        )
+        result = handle_customer_subscription_deleted(
+            {
+                "id": "sub_gone",
+                "status": "canceled",
+                "current_period_end": 1_700_259_200,
+                "metadata": {"user_id": str(self.user.pk)},
+            }
+        )
+        self.assertIsNotNone(result)
+        sub = UserSubscription.objects.get(user=self.user)
+        self.assertEqual(sub.status, UserSubscription.Status.CANCELED)
+        self.assertFalse(sub.cancel_at_period_end)
+        updated = UserAuthEvent.objects.filter(
+            user=self.user,
+            event_type=UserAuthEvent.EventType.SUBSCRIPTION_UPDATED,
+        ).latest("created")
+        self.assertIn("status=canceled", updated.detail)
+
 
 class StripeWebhookViewTestCase(APITestCase):
     def setUp(self):

llm_be/finance/views.py

@@ -199,6 +199,12 @@ class SubscriptionMeView(APIView):
             "stripe_subscription_id": (
                 sub.stripe_subscription_id if sub else ""
             ),
+            "cancel_at_period_end": bool(sub.cancel_at_period_end) if sub else False,
+            "current_period_end": (
+                sub.current_period_end.isoformat()
+                if sub and sub.current_period_end
+                else None
+            ),
             "usage": usage.to_dict(),
         }
         return Response(payload)