diff --git a/backend/apps/account_payment/webhooks.py b/backend/apps/account_payment/webhooks.py
index 8f2b611b..51bb8d4b 100644
--- a/backend/apps/account_payment/webhooks.py
+++ b/backend/apps/account_payment/webhooks.py
@@ -513,6 +513,38 @@ def remove_user(email: str, group_key: str = None, event_context: str = None) ->
         raise
 
 
+def chatbot_trial_just_ended(event: Event) -> bool:
+    """True if the subscription ended while it was still in trial."""
+    data = event.data or {}
+    previous_status = (data.get("previous_attributes") or {}).get("status")
+    if previous_status == "trialing":
+        return True
+
+    obj = data.get("object") or {}
+    trial_end = obj.get("trial_end")
+    ended_at = obj.get("canceled_at") or obj.get("ended_at")
+    if not trial_end or not ended_at:
+        return False
+    return int(ended_at) <= int(trial_end) + 3600
+
+
+def maybe_send_chatbot_trial_ended_email(
+    wc: WebhookContext,
+    subscription: Subscription | None,
+    account: Account | None,
+    *,
+    had_chatbot_access: bool,
+) -> None:
+    """Send the trial-ended email if chatbot access was just revoked for a trial."""
+    if not account or not chatbot_trial_just_ended(wc.event):
+        return
+    if not had_chatbot_access or account.has_chatbot_access:
+        return
+    if not subscription_product_is_chatbot(subscription, wc.event, wc.event_context):
+        return
+    send_chatbot_trial_ended_email(account, event_context=wc.event_context)
+
+
 def send_chatbot_trial_ended_email(account: Account, event_context: str = None) -> None:
     """Send the "your chatbot trial ended" email.
 
@@ -763,8 +795,7 @@ def handle_subscription(event: Event):
     subscription = get_subscription(event, event_context=wc.event_context)
     account = get_account_for_stripe_customer(event)
 
-    status = event.data.get("object", {}).get("status")
-    previous_status = event.data.get("previous_attributes", {}).get("status")
+    status = (event.data.get("object") or {}).get("status")
 
     if status in ["trialing", "active"]:
         if subscription:
@@ -791,18 +822,11 @@ def handle_subscription(event: Event):
             subscription.is_active = False
             subscription.save()
 
-        trial_just_ended = previous_status == "trialing" and account
         had_chatbot_access = bool(account and account.has_chatbot_access)
-
         apply_inactive_subscription_entitlements(wc, subscription, account)
-
-        if (
-            trial_just_ended
-            and had_chatbot_access
-            and not account.has_chatbot_access
-            and subscription_product_is_chatbot(subscription, wc.event, wc.event_context)
-        ):
-            send_chatbot_trial_ended_email(account, event_context=wc.event_context)
+        maybe_send_chatbot_trial_ended_email(
+            wc, subscription, account, had_chatbot_access=had_chatbot_access
+        )
 
 
 @webhooks.handler("customer.subscription.updated")
@@ -833,6 +857,8 @@ def subscribe(event: Event, **kwargs):
 def unsubscribe(event: Event, **kwargs):
     """Revoke entitlements for a deleted Stripe subscription.
 
+    Also sends the chatbot trial-ended email if the subscription was still in trial.
+
     Args:
         event: The `customer.subscription.deleted` Stripe webhook event.
         **kwargs: Unused; accepted for compatibility with the djstripe
@@ -849,7 +875,11 @@ def unsubscribe(event: Event, **kwargs):
         subscription.save()
 
     account = get_account_for_stripe_customer(event)
+    had_chatbot_access = bool(account and account.has_chatbot_access)
     apply_inactive_subscription_entitlements(wc, subscription, account)
+    maybe_send_chatbot_trial_ended_email(
+        wc, subscription, account, had_chatbot_access=had_chatbot_access
+    )
 
 
 @webhooks.handler("customer.subscription.paused")