diff --git a/src/Client.php b/src/Client.php
index bb888a9..f4bf1e6 100644
--- a/src/Client.php
+++ b/src/Client.php
@@ -99,6 +99,22 @@ public function get_user_agent() {
 		);
 	}
 
+	/**
+	 * Helper function to check if the HTTP timeout could be increased.
+	 * 
+	 * @link https://github.com/pronamic/wp-pay-core/issues/170
+	 * @return bool
+	 */
+	private function should_increase_http_timeout() {
+		return (
+			\wp_doing_cron()
+				||
+			\defined( 'WP_CLI' ) && WP_CLI
+				||
+			\defined( 'PRONAMIC_AS_CONTEXT' )
+		);
+	}
+
 	/**
 	 * Send request with the specified action and parameters
 	 *
@@ -117,6 +133,7 @@ public function send_request( $url, $method = 'GET', $data = null ) {
 			'headers'    => [
 				'Authorization' => 'Bearer ' . $this->api_key,
 			],
+			'timeout'    => $this->should_increase_http_timeout() ? 30 : 5,
 		];
 
 		if ( null !== $data ) {