diff --git a/cli/commands/Bulk_Add_Users_Command.php b/cli/commands/Bulk_Add_Users_Command.php
new file mode 100644
index 0000000..f4ad1ac
--- /dev/null
+++ b/cli/commands/Bulk_Add_Users_Command.php
@@ -0,0 +1,356 @@
+<?php
+namespace PMPro_Toolkit;
+
+use WP_CLI;
+use WP_CLI_Command;
+use WP_CLI\Utils;
+
+class Bulk_Add_Users_Command extends WP_CLI_Command {
+
+	/**
+	 * Pool of unused name combinations.
+	 *
+	 * @var array
+	 */
+	private $name_combinations = array();
+
+	/**
+	 * Flag to indicate if the name pool has been initialized.
+	 *
+	 * @var bool
+	 */
+	private $name_pool_initialized = false;
+
+	/**
+	 * Add a large number of new users, optionally with memberships and subscriptions.
+	 *
+	 * ## OPTIONS
+	 *
+	 * [--count=<number>]
+	 * : The number of users to add. Default is 10.
+	 *
+	 * [--password=<password>]
+	 * : The password for the new users. Default is 'password123'.
+	 *
+	 * [--months-back=<number>]
+	 * : The number of months in the past to randomly assign start dates (only used with --with-membership). Default is 1.
+	 *
+	 * [--with-membership]
+	 * : Create users with memberships assigned. Without this flag, only user accounts are created.
+	 *
+	 * [--membership_level_id=<id>]
+	 * : The membership level ID to assign to each user (requires --with-membership). If not specified, levels are randomly assigned.
+	 *
+	 * [--for-siege=<domain>]
+	 * : Output a txt file for Siege with test login POST commands, using the specified domain (e.g., http://example.com).
+	 *
+	 * ## EXAMPLES
+	 *
+	 *     wp pmpro-toolkit bulk-add-users --count=50
+	 *     wp pmpro-toolkit bulk-add-users --count=100 --with-membership --membership_level_id=2
+	 *     wp pmpro-toolkit bulk-add-users --count=100 --with-membership --months-back=6
+	 *     wp pmpro-toolkit bulk-add-users --count=10 --for-siege=[domain including http:// or https://]
+	 */
+	public function __invoke( $args, $assoc_args ) {
+		global $wpdb;
+
+		$count                         = isset( $assoc_args['count'] ) ? intval( $assoc_args['count'] ) : 10;
+		$custom_password               = isset( $assoc_args['password'] ) ? $assoc_args['password'] : 'password123';
+		$with_membership               = isset( $assoc_args['with-membership'] );
+		$specified_membership_level_id = isset( $assoc_args['membership_level_id'] ) ? intval( $assoc_args['membership_level_id'] ) : 0;
+		$months                        = isset( $assoc_args['months-back'] ) ? intval( $assoc_args['months-back'] ) : 1;
+		$siege_lines  = array();
+		$siege_domain = isset( $assoc_args['for-siege'] ) ? rtrim( $assoc_args['for-siege'], '/' ) : '';
+
+		// Validate months-back parameter
+		if ( $months > 6 ) {
+			WP_CLI::error( __( '--months-back cannot be greater than 6. Please specify a value between 1 and 6.', 'pmpro-toolkit' ) );
+			return;
+		}
+
+		// If membership_level_id is provided without --with-membership, show warning
+		if ( $specified_membership_level_id && ! $with_membership ) {
+			WP_CLI::warning( __( '--membership_level_id specified but --with-membership not set. Memberships will not be created.', 'pmpro-toolkit' ) );
+		}
+
+		$level_ids = array();
+
+		// Only fetch levels if we're creating memberships
+		if ( $with_membership ) {
+			// Fetch all active membership levels
+			$levels = $wpdb->get_results(
+				"SELECT id FROM {$wpdb->pmpro_membership_levels} WHERE allow_signups = 1"
+			);
+
+			if ( empty( $levels ) ) {
+				WP_CLI::error( __( 'No available membership levels found. Cannot create memberships.', 'pmpro-toolkit' ) );
+				return;
+			}
+
+			// Build a list of level IDs
+			$level_ids = wp_list_pluck( $levels, 'id' );
+
+			// Validate provided membership_level_id if set
+			if ( $specified_membership_level_id && ! in_array( $specified_membership_level_id, $level_ids, true ) ) {
+				WP_CLI::error(
+					sprintf(
+						__( 'Specified membership level ID %1$d is not valid. Available levels: %2$s', 'pmpro-toolkit' ),
+						$specified_membership_level_id,
+						implode( ', ', $level_ids )
+					)
+				);
+				return;
+			}
+		}
+
+		$batch_size          = 50;
+		$processed_count     = 0;
+		$memberships_batch   = array();
+		$subscriptions_batch = array();
+
+		$operation_text = $with_membership ?
+			__( 'Adding users with memberships', 'pmpro-toolkit' ) :
+			__( 'Adding users', 'pmpro-toolkit' );
+
+		$progress = \WP_CLI\Utils\make_progress_bar( $operation_text, $count );
+
+		for ( $i = 1; $i <= $count; $i++ ) {
+			// Get a unique first/last name combination
+			$name_parts = $this->generate_unique_name();
+			$first_name   = $name_parts['first_name'];
+			$last_name    = $name_parts['last_name'];
+			$display_name = $name_parts['display_name'];
+
+			$username = 'test_' . sanitize_title($display_name) . '_' . uniqid();
+			// Use @pmpro.test domain for testing/demo purposes
+			$email    = $username . '@pmpro.test';
+			$password = $custom_password ?: wp_generate_password( 16, true, true );
+
+			// Prepare user data with names
+			$user_data = array(
+				'user_login'   => $username,
+				'user_pass'    => $password,
+				'user_email'   => $email,
+				'first_name'   => $first_name,
+				'last_name'    => $last_name,
+				'display_name' => $display_name,
+			);
+			$user_id = wp_insert_user( $user_data );
+
+			if ( is_wp_error( $user_id ) ) {
+				WP_CLI::warning(
+					sprintf(
+						__( 'Failed to create user: %s', 'pmpro-toolkit' ),
+						$username
+					)
+				);
+				$progress->tick();
+				continue;
+			}
+
+			// If --for-siege is set, build the Siege test line for this user.
+			if ( $siege_domain ) {
+				$siege_lines[] = sprintf(
+					'%s/wp-json/toolkit/v1/test-login POST {"username":"%s","password":"%s"}',
+					$siege_domain,
+					$username,
+					$password
+				);
+			}
+
+			// Only create membership data if --with-membership flag is set
+			if ( $with_membership ) {
+				$membership_level_id = $specified_membership_level_id ?
+					$specified_membership_level_id :
+					$level_ids[ array_rand( $level_ids ) ];
+
+				// Generate random start date if months > 0, else use current time
+				$startdate = $this->get_random_past_date( $months );
+				$modified  = $startdate;
+
+				$memberships_batch[] = $wpdb->prepare(
+					"(%d, %d, %s, NULL, %s, 'active')",
+					$user_id,
+					$membership_level_id,
+					$startdate,
+					$modified
+				);
+
+				// Calculate next payment date as 1 month after startdate
+				$next_payment_date = date( 'Y-m-d H:i:s', strtotime( '+1 month', strtotime( $startdate ) ) );
+
+				$subscriptions_batch[] = $wpdb->prepare(
+					"(%d, %d, 'stripe', 'test', %s, 'active', %s, %s, 9.99, 1, 'Month', %s)",
+					$user_id,
+					$membership_level_id,
+					uniqid( 'txn_test_' ),
+					$startdate,
+					$next_payment_date,
+					$modified
+				);
+			}
+
+			++$processed_count;
+			$progress->tick();
+
+			// Batch insert every $batch_size users or at the end (only if creating memberships)
+			if ( $with_membership && ( $processed_count % $batch_size === 0 || $i === $count ) ) {
+				if ( ! empty( $memberships_batch ) ) {
+					$result = $wpdb->query(
+						"INSERT INTO {$wpdb->prefix}pmpro_memberships_users 
+                        (user_id, membership_id, startdate, enddate, modified, status) VALUES " .
+						implode( ',', $memberships_batch )
+					);
+
+					if ( false === $result || ! empty( $wpdb->last_error ) ) {
+						WP_CLI::warning(
+							sprintf(
+								__( 'Database error during memberships batch insert: %s', 'pmpro-toolkit' ),
+								$wpdb->last_error
+							)
+						);
+					}
+					$memberships_batch = array();
+				}
+
+				if ( ! empty( $subscriptions_batch ) ) {
+					$result = $wpdb->query(
+						"INSERT INTO {$wpdb->prefix}pmpro_subscriptions 
+                        (user_id, membership_level_id, gateway, gateway_environment, subscription_transaction_id, status, startdate, next_payment_date, billing_amount, cycle_number, cycle_period, modified) VALUES " .
+						implode( ',', $subscriptions_batch )
+					);
+
+					if ( false === $result || ! empty( $wpdb->last_error ) ) {
+						WP_CLI::warning(
+							sprintf(
+								__( 'Database error during subscriptions batch insert: %s', 'pmpro-toolkit' ),
+								$wpdb->last_error
+							)
+						);
+					}
+					$subscriptions_batch = array();
+				}
+			}
+		}
+
+		$progress->finish();
+
+		// If --for-siege was set, output the file.
+		if ( $siege_domain && ! empty( $siege_lines ) ) {
+			$upload_dir = wp_upload_dir();
+			$toolkit_dir = $upload_dir['basedir'] . '/pmpro-toolkit';
+			if ( ! is_dir( $toolkit_dir ) ) {
+				wp_mkdir_p( $toolkit_dir );
+			}
+			$siege_file = sprintf(
+				'%s/siege-users-%s.txt',
+				$toolkit_dir,
+				uniqid()
+			);
+			file_put_contents( $siege_file, implode( "\n", $siege_lines ) );
+			$siege_url = $upload_dir['baseurl'] . '/pmpro-toolkit/' . basename( $siege_file );
+			WP_CLI::log( sprintf(
+				__( 'Siege test file generated: %s', 'pmpro-toolkit' ),
+				esc_url( $siege_url )
+			) );
+		}
+
+		// Build success message based on what was created
+		if ( $with_membership ) {
+			$message = sprintf(
+				__( 'Successfully added %1$d users with memberships. %2$s', 'pmpro-toolkit' ),
+				$processed_count,
+				$specified_membership_level_id
+					? sprintf( __( 'All assigned membership level ID %d.', 'pmpro-toolkit' ), $specified_membership_level_id )
+					: __( 'Membership levels were randomly assigned.', 'pmpro-toolkit' )
+			);
+		} else {
+			$message = sprintf(
+				__( 'Successfully added %d users without memberships.', 'pmpro-toolkit' ),
+				$processed_count
+			);
+		}
+
+		WP_CLI::success( $message );
+	}
+
+	/**
+	 * Helper function to get a random date in the past X months.
+	 *
+	 * @param int $months Number of months back.
+	 * @return string MySQL datetime string.
+	 */
+	private function get_random_past_date( $months ) {
+		if ( $months <= 0 ) {
+			return current_time( 'mysql' );
+		}
+
+		$now       = current_time( 'timestamp' );
+		$earliest  = strtotime( '-' . $months . ' months', $now );
+		$random_ts = mt_rand( $earliest, $now );
+
+		return date( 'Y-m-d H:i:s', $random_ts );
+	}
+
+	/**
+	 * Initialize the name pool with first/last combinations and shuffle.
+	 */
+	private function init_name_pool() {
+	    // Expanded name pools
+	    $first_names = array(
+	        'Alice','Bob','Carol','David','Eve','Frank','Grace','Hank','Ivy','Jack',
+	        'Karen','Liam','Mona','Nate','Olivia','Paul','Quincy','Rachel','Steve','Tina',
+	        'Uma','Victor','Wendy','Xander','Yvonne','Zack','Aaron','Bianca','Cody','Diana',
+	        'Ethan','Fiona','Gavin','Hailey','Ian','Jenna','Kyle','Laura','Miles','Nia',
+	        'Omar','Piper','Quinn','Riley','Sara','Trent','Ursula','Vince','Willow','Xena',
+	        'Yara','Zane','Amber','Blake','Chloe','Derek','Elena','Felix','Gemma','Hudson',
+	        'Isla','Jonah','Kendra','Leon','Maya','Noah','Opal','Preston','Quilla','Roman',
+	        'Selena','Tyler','Ulric','Valeria','Wyatt','Ximena','Yosef','Zephyr','Adrian','Bailey',
+	        'Carmen','Dylan','Ella','Finn','Giselle','Holden','India','Jared','Kylie','Lucas'
+	    );
+	    $last_names = array(
+	        'Smith','Johnson','Williams','Brown','Jones','Miller','Davis','Garcia','Rodriguez','Wilson',
+	        'Anderson','Thomas','Taylor','Moore','Jackson','Martin','Lee','Perez','Thompson','White',
+	        'Harris','Sanchez','Clark','Ramirez','Lewis','Robinson','Walker','Young','Allen','King',
+	        'Wright','Scott','Torres','Nguyen','Hill','Flores','Green','Adams','Nelson','Baker',
+	        'Hall','Rivera','Campbell','Mitchell','Carter','Roberts','Gomez','Phillips','Evans','Turner',
+	        'Diaz','Parker','Cruz','Edwards','Collins','Reyes','Stewart','Morris','Morales','Murphy',
+	        'Cook','Rogers','Gutierrez','Ortiz','Morgan','Cooper','Peterson','Bailey','Reed','Kelly',
+	        'Howard','Ramos','Kim','Cox','Ward','Richardson','Watson','Brooks','Chavez','Wood',
+	        'James','Bennett','Gray','Mendoza','Ruiz','Hughes','Price','Alvarez','Castillo','Sanders'
+	    );
+
+	    // Build combinations
+	    foreach ( $first_names as $first ) {
+	        foreach ( $last_names as $last ) {
+	            $this->name_combinations[] = array(
+	                'first_name' => $first,
+	                'last_name'  => $last,
+	                'display_name' => sprintf( '%s %s', $first, $last ),
+	            );
+	        }
+	    }
+
+	    // Randomize order
+	    shuffle( $this->name_combinations );
+	    $this->name_pool_initialized = true;
+	}
+
+	/**
+	 * Return a unique name combination, initializing pool on first call.
+	 *
+	 * @return array {
+	 *     @type string $first_name
+	 *     @type string $last_name
+	 *     @type string $display_name
+	 * }
+	 */
+	private function generate_unique_name() {
+	    if ( ! $this->name_pool_initialized || empty( $this->name_combinations ) ) {
+	        $this->name_combinations = array();
+	        $this->init_name_pool();
+	    }
+	    // Pop one combination off the pool
+	    return array_pop( $this->name_combinations );
+	}
+}
diff --git a/cli/commands/Bulk_Checkout_Users_Command.php b/cli/commands/Bulk_Checkout_Users_Command.php
new file mode 100644
index 0000000..6258223
--- /dev/null
+++ b/cli/commands/Bulk_Checkout_Users_Command.php
@@ -0,0 +1,170 @@
+<?php
+namespace PMPro_Toolkit;
+
+use WP_CLI;
+use WP_CLI_Command;
+
+class Bulk_Checkout_Users_Command extends WP_CLI_Command {
+
+	/**
+	 * Bulk create users and simulate checkouts for each.
+	 *
+	 * ## OPTIONS
+	 *
+	 * [--count=<number>]
+	 * : Number of users to create and checkout. Default: 100
+	 *
+	 * [--months-back=<number>]
+	 * : Randomize checkout date within the past X months. Default: 1
+	 *
+	 * [--endpoint=<url>]
+	 * : The REST endpoint URL for test checkout. Default: current site URL + /wp-json/toolkit/v1/test-checkout
+	 *
+	 * [--membership_level_id=<id>]
+	 * : The membership level ID to assign to each user.
+	 *
+	 * [--password=<password>]
+	 * : The password for the new users. Default is 'password123'.
+	 *
+	 * ## EXAMPLES
+	 *
+	 *     wp pmpro-toolkit bulk-checkout-users --count=100 --months-back=3
+	 */
+	public function __invoke( $args, $assoc_args ) {
+		$count    = isset( $assoc_args['count'] ) ? intval( $assoc_args['count'] ) : 100;
+		$months   = isset( $assoc_args['months-back'] ) ? intval( $assoc_args['months-back'] ) : 1;
+		$endpoint = isset( $assoc_args['endpoint'] ) ? esc_url_raw( $assoc_args['endpoint'] ) : home_url( '/wp-json/toolkit/v1/test-checkout' );
+
+		// Use Bulk_Add_Users_Command to create users WITHOUT memberships
+		$bulk_add = new \PMPro_Toolkit\Bulk_Add_Users_Command();
+
+		// Store created users by hooking into user_register
+		$created_users = array();
+		add_action(
+			'user_register',
+			function ( $user_id ) use ( &$created_users ) {
+				$user = get_userdata( $user_id );
+				if ( $user ) {
+					$created_users[] = array(
+						'ID'         => $user->ID,
+						'user_login' => $user->user_login,
+						'user_email' => $user->user_email,
+					);
+				}
+			},
+			10,
+			1
+		);
+
+		// Prepare args for Bulk_Add_Users_Command (exclude checkout-specific args and don't create memberships)
+		$user_assoc_args = $assoc_args;
+		unset( $user_assoc_args['endpoint'] );
+		unset( $user_assoc_args['months-back'] ); // We'll handle date randomization in checkout
+		// Explicitly do NOT include --with-membership flag
+
+		WP_CLI::log( __( 'Creating users for checkout simulation...', 'pmpro-toolkit' ) );
+
+		// Call Bulk_Add_Users_Command to create users without memberships
+		$bulk_add->__invoke( $args, $user_assoc_args );
+
+		// Clean up the hook
+		remove_all_actions( 'user_register' );
+
+		if ( empty( $created_users ) ) {
+			WP_CLI::error( __( 'No users were created. Aborting checkout requests.', 'pmpro-toolkit' ) );
+			return;
+		}
+
+		WP_CLI::log(
+			sprintf(
+				__( 'Created %d users. Starting checkout simulation...', 'pmpro-toolkit' ),
+				count( $created_users )
+			)
+		);
+
+		$progress = \WP_CLI\Utils\make_progress_bar( 'Running checkouts for created users', count( $created_users ) );
+		$failed   = 0;
+		$success  = 0;
+
+		foreach ( $created_users as $user ) {
+			// Simulate checkout with date randomization if specified
+			$checkout_date = $this->get_random_checkout_date( $months );
+
+			$payload = array(
+				'user_login'    => $user['user_login'],
+				'user_email'    => $user['user_email'],
+				'skip_gateway'  => true,
+				'cleanup'       => false, // Don't delete users we just created
+				'checkout_date' => $checkout_date, // Add this to endpoint if needed
+			);
+
+			// Add membership level if specified
+			if ( isset( $assoc_args['membership_level_id'] ) ) {
+				$payload['membership_level'] = intval( $assoc_args['membership_level_id'] );
+			}
+
+			$response = wp_remote_post(
+				$endpoint,
+				array(
+					'headers' => array( 'Content-Type' => 'application/json' ),
+					'body'    => wp_json_encode( $payload ),
+					'timeout' => 30,
+				)
+			);
+
+			if ( is_wp_error( $response ) ) {
+				WP_CLI::warning(
+					sprintf(
+						__( 'Checkout failed for %1$s: %2$s', 'pmpro-toolkit' ),
+						$user['user_login'],
+						$response->get_error_message()
+					)
+				);
+				++$failed;
+			} elseif ( wp_remote_retrieve_response_code( $response ) >= 300 ) {
+				WP_CLI::warning(
+					sprintf(
+						__( 'Checkout failed for %1$s: HTTP %2$d', 'pmpro-toolkit' ),
+						$user['user_login'],
+						wp_remote_retrieve_response_code( $response )
+					)
+				);
+				++$failed;
+			} else {
+				++$success;
+			}
+
+			$progress->tick();
+		}
+
+		$progress->finish();
+
+		WP_CLI::log( __( 'Bulk user checkout complete.', 'pmpro-toolkit' ) );
+		WP_CLI::log( sprintf( __( 'Success: %1$d, Failed: %2$d', 'pmpro-toolkit' ), $success, $failed ) );
+
+		if ( $failed === 0 ) {
+			WP_CLI::success( __( 'All checkouts processed successfully.', 'pmpro-toolkit' ) );
+		} else {
+			WP_CLI::warning( sprintf( __( '%d checkouts failed to process.', 'pmpro-toolkit' ), $failed ) );
+		}
+	}
+
+	/**
+	 * Get a random date within the specified months back from now.
+	 *
+	 * @param int $months Number of months back.
+	 * @return string MySQL datetime string.
+	 */
+	private function get_random_checkout_date( $months ) {
+		if ( $months <= 0 ) {
+			return current_time( 'mysql' );
+		}
+
+		$now              = current_time( 'timestamp' );
+		$earliest         = strtotime( '-' . $months . ' months', $now );
+		$random_timestamp = mt_rand( $earliest, $now );
+
+		return date( 'Y-m-d H:i:s', $random_timestamp );
+	}
+}
+
diff --git a/cli/commands/Cleanup_Actions_Command.php b/cli/commands/Cleanup_Actions_Command.php
new file mode 100644
index 0000000..9ce5042
--- /dev/null
+++ b/cli/commands/Cleanup_Actions_Command.php
@@ -0,0 +1,97 @@
+<?php
+namespace PMPro_Toolkit;
+
+use WP_CLI;
+use WP_CLI\Utils;
+use WP_CLI_Command;
+use PMPro_Action_Scheduler;
+
+class Cleanup_Actions_Command {
+
+	/**
+	 * Remove PMPro scheduled actions, optionally filtering by hook, group, status, or args.
+	 *
+	 * ## OPTIONS
+	 *
+	 * [--hook=<hook>]
+	 * : Only delete actions with this hook name.
+	 *
+	 * [--group=<group>]
+	 * : Only delete actions in this group.
+	 *
+	 * [--status=<status>]
+	 * : Only delete actions with this status (default: completed).
+	 *
+	 * [--args=<json_args>]
+	 * : Only delete actions with these exact args. Example: --args='{"user_id":123,"something":"value"}'
+	 *
+	 * ## EXAMPLES
+	 *
+	 *     wp pmpro-toolkit cleanup-actions
+	 *     wp pmpro-toolkit cleanup-actions --hook=pmpro_schedule_daily
+	 *     wp pmpro-toolkit cleanup-actions --hook=pmpro_schedule_hourly --status=pending
+	 *     wp pmpro-toolkit cleanup-actions --group=pmpro_email --status=failed
+	 *     wp pmpro-toolkit cleanup-actions --args='{"user_id":123}'
+	 */
+	public function __invoke( $args, $assoc_args ) {
+		if ( ! class_exists( 'PMPro_Action_Scheduler' ) ) {
+			WP_CLI::error( __( 'PMPro_Action_Scheduler class not found.', 'pmpro-toolkit' ) );
+			return;
+		}
+
+		$hook   = isset( $assoc_args['hook'] ) ? $assoc_args['hook'] : null;
+		$group  = isset( $assoc_args['group'] ) ? $assoc_args['group'] : null;
+		$status = isset( $assoc_args['status'] ) ? $assoc_args['status'] : 'completed';
+
+		// Args can be passed as a JSON string (for advanced/automated use)
+		$args_array = array();
+		if ( isset( $assoc_args['args'] ) && ! empty( $assoc_args['args'] ) ) {
+			$args_json  = $assoc_args['args'];
+			$args_array = json_decode( $args_json, true );
+			if ( ! is_array( $args_array ) ) {
+				WP_CLI::error( __( 'Could not parse --args. Please provide a valid JSON array.', 'pmpro-toolkit' ) );
+				return;
+			}
+		}
+
+		WP_CLI::line( sprintf( __( 'Looking for actions...', 'pmpro-toolkit' ) ) );
+
+		$deleted_count = PMPro_Action_Scheduler::instance()->remove_actions(
+			$hook,
+			$args_array,
+			$group,
+			$status
+		);
+
+		if ( $deleted_count === 0 ) {
+			WP_CLI::success( __( 'No actions found to delete.', 'pmpro-toolkit' ) );
+			return;
+		}
+
+		WP_CLI::success(
+			sprintf(
+				/* translators: %d: count, %s: details */
+				__( 'Deleted %1$d action(s) [%2$s].', 'pmpro-toolkit' ),
+				$deleted_count,
+				$this->build_criteria_description( $hook, $group, $status, $args_array )
+			)
+		);
+	}
+
+	/**
+	 * Helper to describe criteria used in the CLI message.
+	 */
+	private function build_criteria_description( $hook, $group, $status, $args_array ) {
+		$bits = array();
+		if ( $hook ) {
+			$bits[] = "hook: $hook"; }
+		if ( $group ) {
+			$bits[] = "group: $group"; }
+		if ( $status ) {
+			$bits[] = "status: $status"; }
+		if ( ! empty( $args_array ) ) {
+			$bits[] = 'args: ' . json_encode( $args_array );
+		}
+		return $bits ? implode( ', ', $bits ) : __( 'no filter', 'pmpro-toolkit' );
+	}
+}
diff --git a/cli/commands/Expire_Memberships_Command.php b/cli/commands/Expire_Memberships_Command.php
new file mode 100644
index 0000000..67e0c97
--- /dev/null
+++ b/cli/commands/Expire_Memberships_Command.php
@@ -0,0 +1,201 @@
+<?php
+namespace PMPro_Toolkit;
+
+use WP_CLI;
+use WP_CLI_Command;
+use WP_CLI\Utils;
+use PMPro_Scheduled_Actions;
+
+class Expire_Memberships_Command {
+
+	/**
+	 * Update existing users' subscription expiration dates to test expiry functionality.
+	 *
+	 * ## OPTIONS
+	 *
+	 * [--limit=<number>]
+	 * : Limit the number of users to process. Default is 0 (no limit).
+	 *
+	 * [--user_ids=<ids>]
+	 * : Comma-separated list of user IDs to process.
+	 *
+	 * [--days=<n>]
+	 * : Number of days to set the subscription expiration date. Can be positive (future expiry) or negative (already expired). Default is 1.
+	 *
+	 * [--expired]
+	 * : If set, override --days and set expiration date to yesterday (-1).
+	 *
+	 * [--with_as]
+	 * : If set, trigger the membership expiration reminder emails via Action Scheduler.
+	 *
+	 * ## EXAMPLES
+	 *
+	 *     wp pmpro-toolkit expire-memberships
+	 *     wp pmpro-toolkit expire-memberships --limit=10
+	 *     wp pmpro-toolkit expire-memberships --user_ids=1,2,3
+	 *     wp pmpro-toolkit expire-memberships --user_ids=1,2,3 --limit=2
+	 *     wp pmpro-toolkit expire-memberships --days=5
+	 *     wp pmpro-toolkit expire-memberships --days=-3
+	 *     wp pmpro-toolkit expire-memberships --expired
+	 *     wp pmpro-toolkit expire-memberships --with_as
+	 */
+	public function __invoke( $args, $assoc_args ) {
+
+		global $wpdb;
+
+		$limit        = isset( $assoc_args['limit'] ) ? intval( $assoc_args['limit'] ) : 0;
+		$user_ids_arg = isset( $assoc_args['user_ids'] ) ? $assoc_args['user_ids'] : '';
+		$days         = isset( $assoc_args['days'] ) ? intval( $assoc_args['days'] ) : 1;
+		$with_as      = isset( $assoc_args['with_as'] );
+		$expired      = isset( $assoc_args['expired'] );
+
+		if ( $expired ) {
+			$days = -1;
+		}
+
+		if ( ! empty( $user_ids_arg ) ) {
+			$user_ids = array_map( 'intval', array_filter( array_map( 'trim', explode( ',', $user_ids_arg ) ) ) );
+			if ( $limit > 0 ) {
+				$user_ids = array_slice( $user_ids, 0, $limit );
+			}
+		} else {
+			$users = $wpdb->get_col( "SELECT ID FROM {$wpdb->users}" );
+			if ( $limit > 0 ) {
+				$user_ids = array_slice( $users, 0, $limit );
+			} else {
+				$user_ids = $users;
+			}
+		}
+
+		if ( empty( $user_ids ) ) {
+			return; // No users to assign subscriptions to.
+		}
+
+		$processed_count = 0;
+
+		// Initialize a WP-CLI progress bar.
+		$progress = \WP_CLI\Utils\make_progress_bar(
+			sprintf(
+			/* translators: %d: number of users */
+				__( 'Processing %d users', 'pmpro-toolkit' ),
+				count( $user_ids )
+			),
+			count( $user_ids )
+		);
+
+		foreach ( $user_ids as $user_id ) {
+			// Check for an existing subscription.
+			$subscription = $wpdb->get_row(
+				$wpdb->prepare(
+					"SELECT * FROM {$wpdb->prefix}pmpro_subscriptions WHERE user_id = %d AND status = 'active' ORDER BY id DESC LIMIT 1",
+					$user_id
+				)
+			);
+
+			$next_payment_date = date( 'Y-m-d H:i:s', strtotime( "{$days} days" ) );
+
+			// Determine membership_level_id to use
+			if ( $subscription ) {
+				$membership_level_id = $subscription->membership_level_id;
+			} else {
+				// Try to get user's current level from pmpro_memberships_users table
+				$membership_level_id = $wpdb->get_var(
+					$wpdb->prepare(
+						"SELECT membership_id FROM {$wpdb->prefix}pmpro_memberships_users WHERE user_id = %d AND status = 'active' ORDER BY enddate DESC LIMIT 1",
+						$user_id
+					)
+				);
+
+				if ( ! $membership_level_id ) {
+					// Fallback to first available membership level id from pmpro_membership_levels table
+					$membership_level_id = $wpdb->get_var(
+						"SELECT id FROM {$wpdb->prefix}pmpro_membership_levels ORDER BY id ASC LIMIT 1"
+					);
+				}
+			}
+
+			if ( $subscription ) {
+				// Update existing subscription's next payment date.
+				$wpdb->update(
+					"{$wpdb->prefix}pmpro_subscriptions",
+					array(
+						'next_payment_date' => $next_payment_date,
+						'modified'          => current_time( 'mysql' ),
+					),
+					array( 'id' => $subscription->id )
+				);
+			} else {
+				// Insert new subscription.
+				$wpdb->insert(
+					"{$wpdb->prefix}pmpro_subscriptions",
+					array(
+						'user_id'                     => $user_id,
+						'membership_level_id'         => $membership_level_id,
+						'gateway'                     => 'stripe',
+						'gateway_environment'         => 'test',
+						'subscription_transaction_id' => uniqid( 'txn_test_' ),
+						'status'                      => 'active',
+						'startdate'                   => current_time( 'mysql' ),
+						'next_payment_date'           => $next_payment_date,
+						'billing_amount'              => 9.99,
+						'cycle_number'                => 1,
+						'cycle_period'                => 'Month',
+						'modified'                    => current_time( 'mysql' ),
+					)
+				);
+			}
+
+			// Sync pmpro_memberships_users table.
+			$enddate = date( 'Y-m-d H:i:s', strtotime( "{$days} days" ) );
+
+			// Check if a record exists for this user and membership level
+			$existing = $wpdb->get_var(
+				$wpdb->prepare(
+					"SELECT id FROM {$wpdb->prefix}pmpro_memberships_users WHERE user_id = %d AND membership_id = %d",
+					$user_id,
+					$membership_level_id
+				)
+			);
+
+			$data = array(
+				'user_id'       => $user_id,
+				'membership_id' => $membership_level_id,
+				'startdate'     => current_time( 'mysql' ),
+				'enddate'       => $enddate,
+				'modified'      => current_time( 'mysql' ),
+				'status'        => 'active',
+			);
+
+			if ( $existing ) {
+				$wpdb->update( "{$wpdb->prefix}pmpro_memberships_users", $data, array( 'id' => $existing ) );
+			} else {
+				$wpdb->insert( "{$wpdb->prefix}pmpro_memberships_users", $data );
+			}
+
+			// Clear the expiration notice meta so reminders get sent again.
+			delete_user_meta( $user_id, 'pmpro_expiration_notice_' . $membership_level_id );
+
+			++$processed_count;
+			$progress->tick();
+		}
+
+		// Finish the progress bar.
+		$progress->finish();
+
+		$expiry_direction = $days < 0 ? 'already expired' : 'set to expire in the future';
+
+		WP_CLI::success( sprintf( _n( 'Expiring subscription added/updated for %1$d user (%2$s).', 'Expiring subscriptions added/updated for %1$d users (%2$s).', $processed_count, 'pmpro-toolkit' ), $processed_count, $expiry_direction ) );
+
+		// Trigger membership expiration emails via Action Scheduler if applicable.
+		if ( class_exists( 'PMPro_Scheduled_Actions' ) && $with_as ) {
+			WP_CLI::log( 'Triggering membership expiration emails via scheduled actions...' );
+			if ( $expired || $days < 0 ) {
+				PMPro_Scheduled_Actions::instance()->pmpro_expire_memberships();
+				WP_CLI::success( 'Membership expiration emails scheduled.' );
+			} else {
+				PMPro_Scheduled_Actions::instance()->membership_expiration_reminders();
+				WP_CLI::success( 'Membership expiring soon emails scheduled.' );
+			}
+		}
+	}
+}
diff --git a/cli/commands/Payment_Reminders_Command.php b/cli/commands/Payment_Reminders_Command.php
new file mode 100644
index 0000000..2573c80
--- /dev/null
+++ b/cli/commands/Payment_Reminders_Command.php
@@ -0,0 +1,145 @@
+<?php
+namespace PMPro_Toolkit;
+
+use WP_CLI;
+use WP_CLI_Command;
+use WP_CLI\Utils;
+use PMPro_Scheduled_Actions;
+
+/**
+ * Manage recurring payment dates for testing reminders.
+ */
+class Payment_Reminders_Command {
+
+	/**
+	 * Adjust next_payment_date for active subscriptions and clear reminder meta for testing.
+	 *
+	 * ## OPTIONS
+	 *
+	 * [--limit=<number>]
+	 * : Limit the number of subscriptions to process. Default is 0 (no limit).
+	 *
+	 * [--user_ids=<ids>]
+	 * : Comma-separated list of user IDs to process.
+	 *
+	 * [--days=<n>]
+	 * : Set next_payment_date to n days from now (positive = future, negative = past). Default is 7.
+	 *
+	 * [--with_as]
+	 * : If set, trigger the recurring payment reminder scheduler.
+	 *
+	 * ## EXAMPLES
+	 *
+	 *     wp pmpro-toolkit payment-reminders
+	 *     wp pmpro-toolkit payment-reminders --limit=10
+	 *     wp pmpro-toolkit payment-reminders --user_ids=1,2,3
+	 *     wp pmpro-toolkit payment-reminders --days=3
+	 *     wp pmpro-toolkit payment-reminders --with_as
+	 */
+	public function __invoke( $args, $assoc_args ) {
+
+		global $wpdb;
+
+		$limit        = isset( $assoc_args['limit'] ) ? intval( $assoc_args['limit'] ) : 0;
+		$user_ids_arg = isset( $assoc_args['user_ids'] ) ? $assoc_args['user_ids'] : '';
+		$days         = isset( $assoc_args['days'] ) ? intval( $assoc_args['days'] ) : 7;
+		$with_as      = isset( $assoc_args['with_as'] );
+
+		// Get users to process.
+		if ( ! empty( $user_ids_arg ) ) {
+			$user_ids = array_map( 'intval', array_filter( array_map( 'trim', explode( ',', $user_ids_arg ) ) ) );
+		} else {
+			$user_ids = $wpdb->get_col( "SELECT ID FROM {$wpdb->users}" );
+		}
+
+		if ( $limit > 0 ) {
+			$user_ids = array_slice( $user_ids, 0, $limit );
+		}
+
+		if ( empty( $user_ids ) ) {
+			WP_CLI::warning( __( 'No users found to process.', 'pmpro-toolkit' ) );
+			return;
+		}
+
+		$total_users = count( $user_ids );
+		$progress = \WP_CLI\Utils\make_progress_bar( __( 'Processing users', 'pmpro-toolkit' ), $total_users );
+
+		$processed_count = 0;
+		foreach ( $user_ids as $user_id ) {
+			$progress->tick();
+			// Get all active subscriptions for user.
+			$subscriptions = $wpdb->get_results(
+				$wpdb->prepare(
+					"SELECT * FROM {$wpdb->prefix}pmpro_subscriptions WHERE user_id = %d AND status = 'active'",
+					$user_id
+				)
+			);
+
+			if ( empty( $subscriptions ) ) {
+				continue;
+			}
+
+			foreach ( $subscriptions as $subscription ) {
+				$reminder_window = $days > 0 ? $days - 1 : 0;
+				$next_payment_date = date( 'Y-m-d 00:00:00', strtotime( "+{$reminder_window} days", current_time( 'timestamp' ) ) );
+				$wpdb->update(
+					"{$wpdb->prefix}pmpro_subscriptions",
+					array(
+						'next_payment_date' => $next_payment_date,
+						'modified'          => current_time( 'mysql' ),
+					),
+					array( 'id' => $subscription->id )
+				);
+
+				// Remove meta fields related to recurring payment reminders, so reminders get sent again.
+				$wpdb->delete(
+					"{$wpdb->prefix}pmpro_subscriptionmeta",
+					array(
+						'pmpro_subscription_id' => $subscription->id,
+						'meta_key'              => 'pmprorm_last_next_payment_date',
+					)
+				);
+				$wpdb->delete(
+					"{$wpdb->prefix}pmpro_subscriptionmeta",
+					array(
+						'pmpro_subscription_id' => $subscription->id,
+						'meta_key'              => 'pmprorm_last_days',
+					)
+				);
+
+				++$processed_count;
+			}
+		}
+		$progress->finish();
+
+		WP_CLI::success(
+			sprintf(
+				_n(
+					'Adjusted next_payment_date for %d subscription. Cleared reminder meta.',
+					'Adjusted next_payment_date for %d subscriptions. Cleared reminder meta.',
+					$processed_count,
+					'pmpro-toolkit'
+				),
+				$processed_count
+			)
+		);
+
+		// Optionally trigger the scheduler.
+		if ( $with_as && class_exists( 'PMPro_Scheduled_Actions' ) ) {
+			PMPro_Scheduled_Actions::instance()->schedule_recurring_payment_reminder_tasks();
+			// Log the count of scheduled tasks.
+			WP_CLI::success(
+				sprintf(
+					_n(
+						'Scheduled %d recurring payment reminder.',
+						'Scheduled %d recurring payment reminders.',
+						$processed_count,
+						'pmpro-toolkit'
+					),
+					$processed_count
+				)
+			);
+			
+		}
+	}
+}
diff --git a/pmpro-toolkit.php b/pmpro-toolkit.php
index df0b4a8..7305a17 100755
--- a/pmpro-toolkit.php
+++ b/pmpro-toolkit.php
@@ -92,6 +92,16 @@ function pmprodev_init_options() {
 	// Load CLI command class only if enabled via Toolkit setting.
 	require_once plugin_dir_path( __FILE__ ) . 'cli/Toolkit_Commands.php';
 	\WP_CLI::add_command( 'pmpro-toolkit', 'PMPro_Toolkit\\Toolkit_Commands' );
+
+	// Test data commands (one class per command).
+	foreach ( glob( plugin_dir_path( __FILE__ ) . 'cli/commands/*_Command.php' ) as $pmprodev_cli_command_file ) {
+		require_once $pmprodev_cli_command_file;
+	}
+	\WP_CLI::add_command( 'pmpro-toolkit bulk-add-users', 'PMPro_Toolkit\\Bulk_Add_Users_Command' );
+	\WP_CLI::add_command( 'pmpro-toolkit bulk-checkout-users', 'PMPro_Toolkit\\Bulk_Checkout_Users_Command' );
+	\WP_CLI::add_command( 'pmpro-toolkit expire-memberships', 'PMPro_Toolkit\\Expire_Memberships_Command' );
+	\WP_CLI::add_command( 'pmpro-toolkit payment-reminders', 'PMPro_Toolkit\\Payment_Reminders_Command' );
+	\WP_CLI::add_command( 'pmpro-toolkit cleanup-actions', 'PMPro_Toolkit\\Cleanup_Actions_Command' );
 }
 
 /**