diff --git a/inc/Abilities/Email/EmailAbilities.php b/inc/Abilities/Email/EmailAbilities.php
index 3cb952d89..2802ae05c 100644
--- a/inc/Abilities/Email/EmailAbilities.php
+++ b/inc/Abilities/Email/EmailAbilities.php
@@ -510,6 +510,10 @@ public function executeReply( array $input ): array {
 		$sent = wp_mail( $to, $input['subject'], $input['body'], $headers );
 
 		if ( $sent ) {
+			// Save a copy to the IMAP Sent folder so the message appears in
+			// the user's email client (e.g. Gmail "Sent Mail" thread view).
+			$this->saveToSentFolder( $to, $input['subject'], $input['body'], $headers );
+
 			return array(
 				'success' => true,
 				'message' => 'Reply sent to ' . implode( ', ', $to ),
@@ -1287,4 +1291,67 @@ private function buildMailboxString( string $host, int $port, string $encryption
 
 		return sprintf( '{%s:%d%s}%s', $host, $port, $flags, $folder );
 	}
+
+	/**
+	 * Save a sent message to the IMAP Sent folder.
+	 *
+	 * After wp_mail() sends via SMTP, the message only exists on the recipient's
+	 * server. This appends a copy to the sender's Sent folder so it appears in
+	 * their email client (e.g. Gmail thread view).
+	 *
+	 * @param array  $to      Recipient addresses.
+	 * @param string $subject Email subject.
+	 * @param string $body    Email body.
+	 * @param array  $headers Email headers (Content-Type, In-Reply-To, References, etc.).
+	 */
+	private function saveToSentFolder( array $to, string $subject, string $body, array $headers ): void {
+		// Determine the Sent folder name. Gmail uses "[Gmail]/Sent Mail".
+		$sent_folder = '[Gmail]/Sent Mail';
+
+		$connection = $this->connect( $sent_folder );
+		if ( is_array( $connection ) && ! ( $connection['success'] ?? true ) ) {
+			// Non-Gmail server or folder not found — try common alternatives.
+			foreach ( array( 'Sent', 'Sent Items', 'INBOX.Sent' ) as $fallback ) {
+				$connection = $this->connect( $fallback );
+				if ( ! is_array( $connection ) ) {
+					$sent_folder = $fallback;
+					break;
+				}
+			}
+
+			// If still no connection, silently skip — sending succeeded, saving is best-effort.
+			if ( is_array( $connection ) ) {
+				return;
+			}
+		}
+
+		$auth    = $this->getAuthProvider();
+		$from    = $auth ? $auth->getUser() : 'noreply@extrachill.com';
+		$to_str  = implode( ', ', $to );
+		$date    = gmdate( 'r' );
+
+		// Build the RFC822 message.
+		$message  = "From: {$from}\r\n";
+		$message .= "To: {$to_str}\r\n";
+		$message .= "Subject: {$subject}\r\n";
+		$message .= "Date: {$date}\r\n";
+
+		foreach ( $headers as $header ) {
+			$message .= $header . "\r\n";
+		}
+
+		$message .= "MIME-Version: 1.0\r\n";
+		$message .= "\r\n";
+		$message .= $body;
+
+		// phpcs:ignore WordPress.PHP.NoSilencedErrors.Discouraged
+		@imap_append( $connection, $this->buildMailboxString(
+			$auth->getHost(),
+			$auth->getPort(),
+			$auth->getEncryption(),
+			$sent_folder
+		), $message, '\\Seen' );
+
+		imap_close( $connection );
+	}
 }
diff --git a/inc/Abilities/Flow/FlowHelpers.php b/inc/Abilities/Flow/FlowHelpers.php
index b06fa871a..7e8e447b0 100644
--- a/inc/Abilities/Flow/FlowHelpers.php
+++ b/inc/Abilities/Flow/FlowHelpers.php
@@ -517,18 +517,58 @@ protected function applyStepConfigsToFlow( int $flow_id, array $step_configs ):
 				continue;
 			}
 
+			// Normalize plural forms to the singular keys that UpdateFlowStepAbility expects.
+			// CLI and admin UI naturally pass handler_slugs (array) and handler_configs (keyed object),
+			// but the ability expects handler_slug (string) and handler_config (object).
+			$handler_slugs  = $config['handler_slugs'] ?? array();
+			$handler_configs = $config['handler_configs'] ?? array();
+
+			// If singular forms are provided, use those directly (backward compat with --handler-config path).
+			$single_slug   = $config['handler_slug'] ?? '';
+			$single_config = $config['handler_config'] ?? array();
+
+			// When handler_slugs is provided, add each handler with its config from handler_configs.
+			if ( ! empty( $handler_slugs ) ) {
+				foreach ( $handler_slugs as $slug ) {
+					$slug_config = $handler_configs[ $slug ] ?? array();
+					$add_result  = $flow_step_abilities->executeUpdateFlowStep(
+						array(
+							'flow_step_id'     => $flow_step_id,
+							'add_handler'      => $slug,
+							'add_handler_config' => $slug_config,
+						)
+					);
+					if ( ! $add_result['success'] ) {
+						$errors[] = array(
+							'step_type'    => $step_type,
+							'flow_step_id' => $flow_step_id,
+							'handler'      => $slug,
+							'error'        => $add_result['error'] ?? 'Failed to add handler',
+						);
+					}
+				}
+			}
+
+			// Build the base update input for singular handler_slug / handler_config / user_message.
 			$update_input = array( 'flow_step_id' => $flow_step_id );
 
-			if ( ! empty( $config['handler_slug'] ) ) {
-				$update_input['handler_slug'] = $config['handler_slug'];
+			if ( ! empty( $single_slug ) ) {
+				$update_input['handler_slug'] = $single_slug;
 			}
-			if ( ! empty( $config['handler_config'] ) ) {
-				$update_input['handler_config'] = $config['handler_config'];
+			if ( ! empty( $single_config ) ) {
+				$update_input['handler_config'] = $single_config;
 			}
 			if ( ! empty( $config['user_message'] ) ) {
 				$update_input['user_message'] = $config['user_message'];
 			}
 
+			// Only call update if there's something beyond the flow_step_id to apply.
+			if ( count( $update_input ) <= 1 && ! empty( $handler_slugs ) ) {
+				// Already handled via add_handler above — mark as applied.
+				$applied[] = $flow_step_id;
+				continue;
+			}
+
 			$result = $flow_step_abilities->executeUpdateFlowStep( $update_input );
 
 			if ( $result['success'] ) {