diff --git a/modules/ppcp-onboarding/src/OnboardingRESTController.php b/modules/ppcp-onboarding/src/OnboardingRESTController.php
index 4eac5ba72..283cf64be 100644
--- a/modules/ppcp-onboarding/src/OnboardingRESTController.php
+++ b/modules/ppcp-onboarding/src/OnboardingRESTController.php
@@ -12,6 +12,7 @@ namespace WooCommerce\PayPalCommerce\Onboarding;
 use WooCommerce\PayPalCommerce\Vendor\Psr\Container\ContainerInterface;
 use WooCommerce\PayPalCommerce\WcGateway\Gateway\CreditCardGateway;
 use WooCommerce\PayPalCommerce\WcGateway\Gateway\PayPalGateway;
+use WooCommerce\PayPalCommerce\Webhooks\WebhookRegistrar;
 
 /**
  * Exposes and handles REST routes related to onboarding.
@@ -249,7 +250,7 @@ class OnboardingRESTController {
 		}
 
 		$webhook_registrar = $this->container->get( 'webhook.registrar' );
-		$webhook_registrar->unregister();
+		assert( $webhook_registrar instanceof WebhookRegistrar );
 		$webhook_registrar->register();
 
 		return array();
diff --git a/modules/ppcp-webhooks/src/Endpoint/ResubscribeEndpoint.php b/modules/ppcp-webhooks/src/Endpoint/ResubscribeEndpoint.php
index b504cc38a..9fe20a1ed 100644
--- a/modules/ppcp-webhooks/src/Endpoint/ResubscribeEndpoint.php
+++ b/modules/ppcp-webhooks/src/Endpoint/ResubscribeEndpoint.php
@@ -62,8 +62,6 @@ class ResubscribeEndpoint {
 			// Validate nonce.
 			$this->request_data->read_request( $this->nonce() );
 
-			$this->registrar->unregister();
-
 			if ( ! $this->registrar->register() ) {
 				wp_send_json_error( 'Webhook subscription failed.', 500 );
 				return false;
diff --git a/modules/ppcp-webhooks/src/WebhookModule.php b/modules/ppcp-webhooks/src/WebhookModule.php
index 6f8669a8b..e9cc66909 100644
--- a/modules/ppcp-webhooks/src/WebhookModule.php
+++ b/modules/ppcp-webhooks/src/WebhookModule.php
@@ -152,7 +152,6 @@ class WebhookModule implements ModuleInterface {
 				add_action(
 					'init',
 					function () use ( $registrar ) {
-						$registrar->unregister();
 						$registrar->register();
 					}
 				);
diff --git a/modules/ppcp-webhooks/src/WebhookRegistrar.php b/modules/ppcp-webhooks/src/WebhookRegistrar.php
index 03769aa61..8f8919ec2 100644
--- a/modules/ppcp-webhooks/src/WebhookRegistrar.php
+++ b/modules/ppcp-webhooks/src/WebhookRegistrar.php
@@ -88,6 +88,8 @@ class WebhookRegistrar {
 	 * @return bool
 	 */
 	public function register(): bool {
+		$this->unregister();
+
 		$webhook = $this->webhook_factory->for_url_and_events(
 			$this->rest_endpoint->url(),
 			$this->rest_endpoint->handled_event_types()
@@ -113,27 +115,23 @@ class WebhookRegistrar {
 
 	/**
 	 * Unregister webhooks with PayPal.
-	 *
-	 * @return bool
 	 */
-	public function unregister(): bool {
-		$data = (array) get_option( self::KEY, array() );
-		if ( ! $data ) {
-			return false;
-		}
+	public function unregister(): void {
 		try {
-			$webhook = $this->webhook_factory->from_array( $data );
-			$success = $this->endpoint->delete( $webhook );
+			$webhooks = $this->endpoint->list();
+			foreach ( $webhooks as $webhook ) {
+				try {
+					$this->endpoint->delete( $webhook );
+				} catch ( RuntimeException $deletion_error ) {
+					$this->logger->error( "Failed to delete webhook {$webhook->id()}: {$deletion_error->getMessage()}" );
+				}
+			}
 		} catch ( RuntimeException $error ) {
 			$this->logger->error( 'Failed to delete webhooks: ' . $error->getMessage() );
-			return false;
 		}
 
-		if ( $success ) {
-			delete_option( self::KEY );
-			$this->last_webhook_event_storage->clear();
-			$this->logger->info( 'Webhooks deleted.' );
-		}
-		return $success;
+		delete_option( self::KEY );
+		$this->last_webhook_event_storage->clear();
+		$this->logger->info( 'Webhooks deleted.' );
 	}
 }