diff --git a/includes/reader-revenue/class-stripe-connection.php b/includes/reader-revenue/class-stripe-connection.php
index 58b3b1fe17..929738e11f 100644
--- a/includes/reader-revenue/class-stripe-connection.php
+++ b/includes/reader-revenue/class-stripe-connection.php
@@ -662,9 +662,10 @@ public static function receive_webhook( $request ) {
 					return $customer;
 				}
 
+				$active_subs = 0;
 				if ( Donations::is_woocommerce_suite_active() ) {
 					if ( $payload['ended_at'] ) {
-						WooCommerce_Connection::end_subscription(
+						$active_subs = WooCommerce_Connection::end_subscription(
 							$payload['id'],
 							$payload['ended_at']
 						);
@@ -679,7 +680,7 @@ public static function receive_webhook( $request ) {
 							Newspack_Newsletters::$metadata_keys['sub_end_date']   => $sub_end_date,
 						],
 					];
-					if ( in_array( $payload['plan']['interval'], [ 'month', 'year' ] ) ) {
+					if ( 0 === $active_subs && in_array( $payload['plan']['interval'], [ 'month', 'year' ] ) ) {
 						$membership_status = 'Ex-' . self::get_membership_status_field_value( $payload['plan']['interval'] );
 						$contact['metadata'][ Newspack_Newsletters::$metadata_keys['membership_status'] ] = $membership_status;
 					}
diff --git a/includes/reader-revenue/class-woocommerce-connection.php b/includes/reader-revenue/class-woocommerce-connection.php
index 7a75627ad5..b2c3d3654d 100644
--- a/includes/reader-revenue/class-woocommerce-connection.php
+++ b/includes/reader-revenue/class-woocommerce-connection.php
@@ -542,10 +542,14 @@ public static function create_transaction( $order_data ) {
 	 *
 	 * @param string $stripe_subscription_id Stripe subscription ID.
 	 * @param int    $end_date Timestamp of when to cancel the subscription.
+	 *
+	 * @return int Number of remaining active subscriptions for the user.
 	 */
 	public static function end_subscription( $stripe_subscription_id, $end_date ) {
 		$subscription = self::get_subscription_by_stripe_subscription_id( $stripe_subscription_id );
+		$active_subs  = 0;
 		if ( $subscription ) {
+			$wc_user_id = $subscription->get_user_id();
 			$subscription->delete_date( 'next_payment' );
 			$subscription->update_dates(
 				[
@@ -555,7 +559,19 @@ public static function end_subscription( $stripe_subscription_id, $end_date ) {
 			$subscription->set_status( 'cancelled' );
 			$subscription->save();
 			Logger::log( 'Cancelled WC subscription with id: ' . $subscription->get_id() );
+
+			if ( $wc_user_id && function_exists( 'wcs_get_users_subscriptions' ) ) {
+				$all_subs = \wcs_get_users_subscriptions( $wc_user_id );
+
+				foreach ( $all_subs as $sub ) {
+					if ( 'active' === $sub->get_status() ) {
+						$active_subs ++;
+					}
+				}
+			}
 		}
+
+		return $active_subs;
 	}
 
 	/**