diff --git a/crates/collab/src/api/billing.rs b/crates/collab/src/api/billing.rs
index 70b9585736cbfc96fe4fb65e24ae53cc94f86392..cb6a31aad229efb6d4424291fb99612c2be2f4bd 100644
--- a/crates/collab/src/api/billing.rs
+++ b/crates/collab/src/api/billing.rs
@@ -1185,6 +1185,21 @@ async fn sync_subscription(
             .await?;
     }
 
+    if let Some(stripe_billing) = app.stripe_billing.as_ref() {
+        if subscription.status == SubscriptionStatus::Canceled
+            || subscription.status == SubscriptionStatus::Paused
+        {
+            let stripe_customer_id = billing_customer
+                .stripe_customer_id
+                .parse::<stripe::CustomerId>()
+                .context("failed to parse Stripe customer ID from database")?;
+
+            stripe_billing
+                .subscribe_to_zed_free(stripe_customer_id)
+                .await?;
+        }
+    }
+
     Ok(billing_customer)
 }
 
diff --git a/crates/collab/src/stripe_billing.rs b/crates/collab/src/stripe_billing.rs
index 23cc9c02e2ebb9ba9beddecf832eb62196bb1099..78680faf57494596470c55f7adc42f85dcd04861 100644
--- a/crates/collab/src/stripe_billing.rs
+++ b/crates/collab/src/stripe_billing.rs
@@ -263,6 +263,24 @@ impl StripeBilling {
         Ok(session.url.context("no checkout session URL")?)
     }
 
+    pub async fn subscribe_to_zed_free(
+        &self,
+        customer_id: stripe::CustomerId,
+    ) -> Result<stripe::Subscription> {
+        let zed_free_price_id = self.zed_free_price_id().await?;
+
+        let mut params = stripe::CreateSubscription::new(customer_id);
+        params.items = Some(vec![stripe::CreateSubscriptionItems {
+            price: Some(zed_free_price_id.to_string()),
+            quantity: Some(1),
+            ..Default::default()
+        }]);
+
+        let subscription = stripe::Subscription::create(&self.client, params).await?;
+
+        Ok(subscription)
+    }
+
     pub async fn checkout_with_zed_free(
         &self,
         customer_id: stripe::CustomerId,