diff --git a/crates/component_subsystem/billing/src/stripe/webhook_event_handlers/customer_subscription/customer_subscription_deleted_handler.rs b/crates/component_subsystem/billing/src/stripe/webhook_event_handlers/customer_subscription/customer_subscription_deleted_handler.rs
index 079f748806..bc520a22d0 100644
--- a/crates/component_subsystem/billing/src/stripe/webhook_event_handlers/customer_subscription/customer_subscription_deleted_handler.rs
+++ b/crates/component_subsystem/billing/src/stripe/webhook_event_handlers/customer_subscription/customer_subscription_deleted_handler.rs
@@ -4,6 +4,10 @@ use crate::stripe::webhook_event_handlers::stripe_webhook_summary::StripeWebhook
 use log::{error, warn};
 use sqlx::MySqlPool;
 use stripe::Subscription;
+use database_queries::queries::billing::subscriptions::get_subscription_by_stripe_id::get_subscription_by_stripe_id;
+use database_queries::queries::billing::subscriptions::upsert_subscription_by_stripe_id::UpsertSubscriptionByStripeId;
+use reusable_types::stripe::stripe_subscription_status::StripeSubscriptionStatus;
+use crate::stripe::webhook_event_handlers::customer_subscription::calculate_subscription_end_date::calculate_subscription_end_date;
 
 /// Handle event type: 'customer.subscription.deleted'
 /// Sent when a customer’s subscription ends.
@@ -17,11 +21,67 @@ pub async fn customer_subscription_deleted_handler(
         StripeWebhookError::ServerError // NB: This was probably *our* fault.
       })?;
 
+  let mut should_process_update = true;
+
+  let mut action_was_taken = false;
+  let mut should_ignore_retry = false;
+
+  // NB: It's possible to receive events out of order.
+  let maybe_existing_subscription = get_subscription_by_stripe_id(&summary.stripe_subscription_id, &mysql_pool)
+      .await
+      .map_err(|err| {
+        error!("Mysql error: {:?}", err);
+        StripeWebhookError::ServerError
+      })?;
+
+  if let Some(existing_subscription) = maybe_existing_subscription {
+    match existing_subscription.maybe_stripe_subscription_status {
+      Some(StripeSubscriptionStatus::Canceled) => {
+        // NB: This is a terminal status and the subscription cannot be updated any further.
+        should_process_update = false;
+        should_ignore_retry = true;
+      }
+      _ => {}
+    }
+  }
+
+  // NB: Even if we haven't received a record before, we should still be able to "tombstone" it
+  // once we detect the deletion.
+  if should_process_update {
+    let upsert = UpsertSubscriptionByStripeId {
+      stripe_subscription_id: &summary.stripe_subscription_id,
+      maybe_user_token: summary.user_token.as_deref(),
+      subscription_category: "todo",
+      subscription_product_key: "todo",
+      maybe_stripe_product_id: Some(&summary.stripe_product_id),
+      maybe_stripe_customer_id: Some(&summary.stripe_customer_id),
+      maybe_stripe_recurring_interval: Some(summary.subscription_interval),
+      maybe_stripe_subscription_status: Some(summary.stripe_subscription_status),
+      maybe_stripe_is_production: Some(summary.stripe_is_production),
+      subscription_start_at: summary.subscription_start_date,
+      current_billing_period_start_at: summary.current_billing_period_start,
+      current_billing_period_end_at: summary.current_billing_period_end,
+      subscription_expires_at: calculate_subscription_end_date(&summary),
+      maybe_cancel_at: summary.maybe_cancel_at,
+      maybe_canceled_at: summary.maybe_canceled_at,
+    };
+
+    let _r = upsert.upsert(mysql_pool)
+        .await
+        .map_err(|err| {
+          error!("Mysql error: {:?}", err);
+          StripeWebhookError::ServerError
+        })?;
+
+    action_was_taken = true;
+    should_ignore_retry = true;
+  }
+
   Ok(StripeWebhookSummary {
     maybe_user_token: summary.user_token,
     maybe_event_entity_id: Some(summary.stripe_subscription_id),
     maybe_stripe_customer_id: Some(summary.stripe_customer_id),
-    action_was_taken: false,
-    should_ignore_retry: false,
+    action_was_taken,
+    should_ignore_retry,
   })
 }
diff --git a/crates/component_subsystem/billing/src/stripe/webhook_event_handlers/customer_subscription/customer_subscription_updated_handler.rs b/crates/component_subsystem/billing/src/stripe/webhook_event_handlers/customer_subscription/customer_subscription_updated_handler.rs
index 640950662a..36e21ad69c 100644
--- a/crates/component_subsystem/billing/src/stripe/webhook_event_handlers/customer_subscription/customer_subscription_updated_handler.rs
+++ b/crates/component_subsystem/billing/src/stripe/webhook_event_handlers/customer_subscription/customer_subscription_updated_handler.rs
@@ -45,8 +45,6 @@ pub async fn customer_subscription_updated_handler(
     }
   }
 
-  // TODO: record cancel_at (future_cancel_at), canceled_at, ended_at (if subscription ended, when it ended), start_date
-
   if should_process_update {
     let upsert = UpsertSubscriptionByStripeId {
       stripe_subscription_id: &summary.stripe_subscription_id,