diff --git a/backend/btrixcloud/emailsender.py b/backend/btrixcloud/emailsender.py
index ab157673..06f5311d 100644
--- a/backend/btrixcloud/emailsender.py
+++ b/backend/btrixcloud/emailsender.py
@@ -28,6 +28,7 @@ class EmailSender:
     smtp_port: int
     smtp_use_tls: bool
     support_email: str
+    survey_url: str
 
     templates: Jinja2Templates
 
@@ -38,6 +39,7 @@ class EmailSender:
         self.password = os.environ.get("EMAIL_PASSWORD") or ""
         self.reply_to = os.environ.get("EMAIL_REPLY_TO") or self.sender
         self.support_email = os.environ.get("EMAIL_SUPPORT") or self.reply_to
+        self.survey_url = os.environ.get("USER_SURVEY_URL") or ""
         self.smtp_server = os.environ.get("EMAIL_SMTP_HOST")
         self.smtp_port = int(os.environ.get("EMAIL_SMTP_PORT", 587))
         self.smtp_use_tls = is_bool(os.environ.get("EMAIL_SMTP_USE_TLS"))
@@ -160,3 +162,27 @@ class EmailSender:
         self._send_encrypted(
             receiver_email, "failed_bg_job", job=job, org=org, finished=finished
         )
+
+    def send_subscription_will_be_canceled(
+        self,
+        cancel_date: datetime,
+        user_name: str,
+        receiver_email: str,
+        org: Organization,
+        headers=None,
+    ):
+        """Send email indicating subscription is cancelled and all org data will be deleted"""
+
+        origin = get_origin(headers)
+        org_url = f"{origin}/orgs/{org.slug}/"
+
+        self._send_encrypted(
+            receiver_email,
+            "sub_cancel",
+            org_url=org_url,
+            user_name=user_name,
+            org_name=org.name,
+            cancel_date=cancel_date,
+            support_email=self.support_email,
+            survey_url=self.survey_url,
+        )
diff --git a/backend/btrixcloud/orgs.py b/backend/btrixcloud/orgs.py
index e33c1d76..e5b1ae47 100644
--- a/backend/btrixcloud/orgs.py
+++ b/backend/btrixcloud/orgs.py
@@ -276,6 +276,16 @@ class OrgOps:
 
         return Organization.from_dict(res)
 
+    async def get_users_for_org(
+        self, org: Organization, min_role=UserRole.VIEWER
+    ) -> List[User]:
+        """get users for org"""
+        uuid_ids = [UUID(id_) for id_, role in org.users.items() if role >= min_role]
+        users: List[User] = []
+        async for user_dict in self.users_db.find({"id": {"$in": uuid_ids}}):
+            users.append(User(**user_dict))
+        return users
+
     async def get_org_by_id(self, oid: UUID) -> Organization:
         """Get an org by id"""
         res = await self.orgs.find_one({"_id": oid})
@@ -489,7 +499,7 @@ class OrgOps:
         org_data = await self.orgs.find_one_and_update(
             {"subscription.subId": update.subId},
             {"$set": query},
-            return_document=ReturnDocument.AFTER,
+            return_document=ReturnDocument.BEFORE,
         )
         if not org_data:
             return None
diff --git a/backend/btrixcloud/subs.py b/backend/btrixcloud/subs.py
index 5cb4d779..fd4a3596 100644
--- a/backend/btrixcloud/subs.py
+++ b/backend/btrixcloud/subs.py
@@ -4,7 +4,9 @@ Subscription API handling
 
 from typing import Callable, Union, Any, Optional, Tuple, List
 import os
+import asyncio
 from uuid import UUID
+from datetime import datetime
 
 from fastapi import Depends, HTTPException, Request
 import aiohttp
@@ -114,8 +116,38 @@ class SubOps:
             )
 
         await self.add_sub_event("update", update, org.id)
+
+        if update.futureCancelDate and self.should_send_cancel_email(org, update):
+            asyncio.create_task(self.send_cancel_emails(update.futureCancelDate, org))
+
         return {"updated": True}
 
+    def should_send_cancel_email(self, org: Organization, update: SubscriptionUpdate):
+        """Should we sent a cancellation email"""
+        if not update.futureCancelDate:
+            return False
+
+        if not org.subscription:
+            return False
+
+        # new cancel date, send
+        if update.futureCancelDate != org.subscription.futureCancelDate:
+            return True
+
+        # if 'trialing_canceled', send
+        if update.status == "trialing_canceled":
+            return True
+
+        return False
+
+    async def send_cancel_emails(self, cancel_date: datetime, org: Organization):
+        """Asynchronously send cancellation emails to all org admins"""
+        users = await self.org_ops.get_users_for_org(org, UserRole.OWNER)
+        for user in users:
+            self.user_manager.email.send_subscription_will_be_canceled(
+                cancel_date, user.name, user.email, org
+            )
+
     async def cancel_subscription(self, cancel: SubscriptionCancel) -> dict[str, bool]:
         """delete subscription data, and unless if readOnlyOnCancel is true, the entire org"""
 
diff --git a/chart/email-templates/sub_cancel b/chart/email-templates/sub_cancel
new file mode 100644
index 00000000..bcb780f6
--- /dev/null
+++ b/chart/email-templates/sub_cancel
@@ -0,0 +1,43 @@
+Your Browsertrix Subscription Has Been Canceled
+~~~
+<html>
+<body>
+<p>Hello {{ user_name }},</p>
+
+<p>The Browsertrix subscription for "{{ org_name }}" has been cancelled at the end of this
+subscription period.</p>
+
+<p style="font-weight: bold">All data hosted on Browsertrix under: <a href="{{ org_url}}">{{ org_url }}</a> will be deleted on {{ cancel_date }}</p>
+
+<p>You can continue to use Browsertrix and download your data before this date. If you change your mind, you can still resubscribe
+by going to <i>Settings -> Billing</i> tab after logging in.</p>
+
+{% if survey_url %}
+<p>We hope you enjoyed using Browsertrix!</p>
+
+<p>To help us make Browsertrix better, we would be very grateful if you could complete <a href="{{ survey_url }}">a quick survey</a> about your experience using Browsertrix.</p>
+{% endif %}
+
+{% if support_email %}
+<p>If you'd like us to keep your data longer or have other questions, you can still reach out to us at: <a href="mailto:{{ support_email }}">{{ support_email }}</a>
+{% endif %}
+~~~
+Hello {{ name }},
+
+The Browsertrix subscription for "{{ org_name }}" has been cancelled at the end of this
+subscription period.
+
+All data hosted on Browsertrix under: {{ org_url }} will be deleted on {{ cancel_date }}
+
+You can continue to use Browsertrix and download your data before this date. If you change your mind, you can still resubscribe
+by going to Settings -> Billing tab after logging in.
+
+{% if survey_url %}
+We hoped you enjoyed using Browsertrix!
+
+To help us make Browsertrix better, we would be very grateful if you could complete a quick survey about your experience with Browsertrix: {{ survey_url }}
+{% endif %}
+
+{% if support_email %}
+If you'd like us to keep your data longer or have other questions, you can still reach out to us at: {{ support_email }}
+{% endif %}
diff --git a/chart/templates/configmap.yaml b/chart/templates/configmap.yaml
index a027e35e..4da46697 100644
--- a/chart/templates/configmap.yaml
+++ b/chart/templates/configmap.yaml
@@ -75,6 +75,8 @@ data:
 
   SALES_EMAIL: "{{ .Values.sales_email }}"
 
+  USER_SURVEY_URL: "{{ .Values.user_survey_url }}"
+
   LOG_SENT_EMAILS: "{{ .Values.email.log_sent_emails }}"
 
   BACKEND_IMAGE: "{{ .Values.backend_image }}"
@@ -194,7 +196,7 @@ metadata:
 
 data:
 {{- $email_templates := .Values.email.templates | default dict }}
-{{- range tuple "failed_bg_job" "invite" "password_reset" "validate" }}
+{{- range tuple "failed_bg_job" "invite" "password_reset" "validate" "sub_cancel" }}
   {{ . }}: |
 {{ ((get $email_templates . ) | default ($.Files.Get (printf "%s/%s" "email-templates" . ))) | indent 4 }}
   {{- end }}
diff --git a/chart/values.yaml b/chart/values.yaml
index d8d62c48..2caeb1c5 100644
--- a/chart/values.yaml
+++ b/chart/values.yaml
@@ -122,6 +122,11 @@ sign_up_url: ""
 # set e-mail to show for subscriptions related info
 sales_email: ""
 
+
+# survey e-mail
+# if set, subscription cancellation e-mails will include a link to this survey
+user_survey_url: ""
+
 # if set, print last 'log_failed_crawl_lines' of each failed
 # crawl pod to backend operator stdout
 # mostly intended for debugging / testing
diff --git a/frontend/src/features/org/org-status-banner.ts b/frontend/src/features/org/org-status-banner.ts
index 90ed61a8..947f93a4 100644
--- a/frontend/src/features/org/org-status-banner.ts
+++ b/frontend/src/features/org/org-status-banner.ts
@@ -80,7 +80,11 @@ export class OrgStatusBanner extends BtrixElement {
       });
     }
 
-    const isTrial = subscription?.status === SubscriptionStatus.Trialing;
+    const isTrialingCanceled =
+      subscription?.status == SubscriptionStatus.TrialingCanceled;
+    const isTrial =
+      subscription?.status === SubscriptionStatus.Trialing ||
+      isTrialingCanceled;
 
     // show banner if < this many days of trial is left
     const MAX_TRIAL_DAYS_SHOW_BANNER = 4;
@@ -120,8 +124,8 @@ export class OrgStatusBanner extends BtrixElement {
           !readOnly &&
           !readOnlyOnCancel &&
           !!futureCancelDate &&
-          isTrial &&
-          daysDiff < MAX_TRIAL_DAYS_SHOW_BANNER,
+          ((isTrial && daysDiff < MAX_TRIAL_DAYS_SHOW_BANNER) ||
+            isTrialingCanceled),
 
         content: () => {
           return {
@@ -138,7 +142,7 @@ export class OrgStatusBanner extends BtrixElement {
               <p>
                 ${msg(
                   html`Your free trial ends on ${dateStr}. To continue using
-                    Browsertrix, select <strong>Choose Plan</strong> in
+                    Browsertrix, select <strong>Subscribe Now</strong> in
                     ${billingTabLink}.`,
                 )}
               </p>
diff --git a/frontend/src/pages/org/settings/components/billing.ts b/frontend/src/pages/org/settings/components/billing.ts
index 1011defe..dbb62943 100644
--- a/frontend/src/pages/org/settings/components/billing.ts
+++ b/frontend/src/pages/org/settings/components/billing.ts
@@ -41,6 +41,7 @@ export class OrgSettingsBilling extends BtrixElement {
     let label = msg("Manage Billing");
 
     switch (subscription.status) {
+      case SubscriptionStatus.TrialingCanceled:
       case SubscriptionStatus.Trialing: {
         label = msg("Subscribe Now");
         break;
@@ -140,7 +141,9 @@ export class OrgSettingsBilling extends BtrixElement {
                         ></sl-icon>
                         <div>
                           ${org.subscription.status ===
-                          SubscriptionStatus.Trialing
+                            SubscriptionStatus.Trialing ||
+                          org.subscription.status ===
+                            SubscriptionStatus.TrialingCanceled
                             ? html`
                                 <span class="font-medium text-neutral-700">
                                   ${msg(
@@ -183,7 +186,9 @@ export class OrgSettingsBilling extends BtrixElement {
                 org.subscription
                   ? html` <p class="mb-3 leading-normal">
                         ${org.subscription.status ===
-                        SubscriptionStatus.Trialing
+                          SubscriptionStatus.Trialing ||
+                        org.subscription.status ===
+                          SubscriptionStatus.TrialingCanceled
                           ? msg(
                               str`To continue using Browsertrix at the end of your trial, click “${this.portalUrlLabel}”.`,
                             )
@@ -269,6 +274,7 @@ export class OrgSettingsBilling extends BtrixElement {
           `;
           break;
         }
+        case SubscriptionStatus.TrialingCanceled:
         case SubscriptionStatus.Trialing: {
           statusLabel = html`
             <span class="text-success-700">${msg("Free Trial")}</span>
diff --git a/frontend/src/types/billing.ts b/frontend/src/types/billing.ts
index 24d1dfa9..2aaa5011 100644
--- a/frontend/src/types/billing.ts
+++ b/frontend/src/types/billing.ts
@@ -5,6 +5,7 @@ import { apiDateSchema } from "./api";
 export enum SubscriptionStatus {
   Active = "active",
   Trialing = "trialing",
+  TrialingCanceled = "trialing_canceled",
   PausedPaymentFailed = "paused_payment_failed",
   Cancelled = "cancelled",
 }