diff --git a/inc/Core/Database/Chat/Chat.php b/inc/Core/Database/Chat/Chat.php
index d9c08572e..133d685b3 100644
--- a/inc/Core/Database/Chat/Chat.php
+++ b/inc/Core/Database/Chat/Chat.php
@@ -486,6 +486,75 @@ public function get_session( string $session_id ): ?array {
 		return $session;
 	}
 
+	/**
+	 * List transcript sessions for a workspace/user pair.
+	 *
+	 * @param WP_Agent_Workspace_Scope $workspace Workspace owning the sessions.
+	 * @param int                      $user_id   WordPress user ID owning the sessions.
+	 * @param array                    $args      Optional filters/pagination.
+	 * @return array<int,array<string,mixed>> Session rows.
+	 */
+	public function list_sessions( WP_Agent_Workspace_Scope $workspace, int $user_id, array $args = array() ): array {
+		global $wpdb;
+
+		$table_name       = self::get_prefixed_table_name();
+		$include_messages = (bool) ( $args['include_messages'] ?? true );
+		$limit            = max( 1, min( 100, (int) ( $args['limit'] ?? 20 ) ) );
+		$offset           = max( 0, (int) ( $args['offset'] ?? 0 ) );
+		$where            = array(
+			'workspace_type = %s',
+			'workspace_id = %s',
+			'user_id = %d',
+		);
+		$query_args       = array(
+			$table_name,
+			$workspace->workspace_type,
+			$workspace->workspace_id,
+			$user_id,
+		);
+
+		if ( is_string( $args['context'] ?? null ) && '' !== $args['context'] ) {
+			$where[]      = 'mode = %s';
+			$query_args[] = $args['context'];
+		}
+
+		if ( is_string( $args['agent_slug'] ?? null ) && '' !== $args['agent_slug'] ) {
+			try {
+				$identity = self::resolve_agent_identity_for_session( $args['agent_slug'] );
+			} catch ( \InvalidArgumentException $e ) {
+				unset( $e );
+				return array();
+			}
+
+			$where[]      = 'agent_id = %d';
+			$query_args[] = $identity['agent_id'];
+		}
+
+		$select = $include_messages ? '*' : 'session_id, workspace_type, workspace_id, user_id, agent_id, title, metadata, provider, model, provider_response_id, mode, created_at, updated_at, last_read_at, expires_at';
+		$sql    = 'SELECT ' . $select . ' FROM %i WHERE ' . implode( ' AND ', $where ) . ' ORDER BY updated_at DESC LIMIT %d OFFSET %d';
+
+		$query_args[] = $limit;
+		$query_args[] = $offset;
+
+		// phpcs:ignore WordPress.DB.DirectDatabaseQuery.DirectQuery,WordPress.DB.DirectDatabaseQuery.NoCaching,WordPress.DB.PreparedSQL.NotPrepared
+		$sessions = $wpdb->get_results( $wpdb->prepare( $sql, ...$query_args ), ARRAY_A );
+
+		if ( ! $sessions ) {
+			return array();
+		}
+
+		foreach ( $sessions as &$session ) {
+			if ( $include_messages ) {
+				$session['messages'] = self::normalize_messages( json_decode( $session['messages'] ?? '[]', true ) ?? array() );
+			}
+			$session['metadata']   = json_decode( $session['metadata'] ?? '[]', true ) ?? array();
+			$session['agent_slug'] = self::resolve_agent_slug_from_session_row( $session );
+		}
+		unset( $session );
+
+		return $sessions;
+	}
+
 	/**
 	 * Resolve the generic transcript agent slug from a stored session row.
 	 *
diff --git a/inc/bootstrap.php b/inc/bootstrap.php
index 115f36e18..ee13243f6 100644
--- a/inc/bootstrap.php
+++ b/inc/bootstrap.php
@@ -136,67 +136,75 @@ function () {
 	0
 );
 
-// Shared layer — site-wide context, visible to all agents.
-// Composable: content assembled from sections registered against SectionRegistry
-// (see inc/migrations/site-md.php). `editable` is forced to false by composable=true.
-MemoryFileRegistry::register( 'SITE.md', 10, array(
-	'layer'       => MemoryFileRegistry::LAYER_SHARED,
-	'protected'   => true,
-	'composable'  => true,
-	'modes'       => array( MemoryFileRegistry::MODE_ALL ),
-	'label'       => 'Site Context',
-	'description' => 'Auto-generated site context. Composable — extend via SectionRegistry.',
-) );
-MemoryFileRegistry::register( 'RULES.md', 15, array(
-	'layer'       => MemoryFileRegistry::LAYER_SHARED,
-	'protected'   => true,
-	'editable'    => 'manage_options',
-	'modes'       => array( MemoryFileRegistry::MODE_ALL ),
-	'label'       => 'Site Rules',
-	'description' => 'Behavioral constraints that apply to every agent. Admin-editable.',
-) );
-
-// Agent layer — identity and knowledge, scoped to a single agent.
-// Injected in interactive modes only (chat, pipeline). Excluded from
-// system mode so autonomous maintenance tasks (e.g. daily memory
-// compaction) are not primed with the agent's identity while operating
-// on these files.
-MemoryFileRegistry::register( 'SOUL.md', 20, array(
-	'layer'       => MemoryFileRegistry::LAYER_AGENT,
-	'protected'   => true,
-	'modes'       => array( 'chat', 'pipeline' ),
-	'label'       => 'Agent Identity',
-	'description' => 'Agent identity, voice, rules. Injected in interactive modes only.',
-) );
-MemoryFileRegistry::register( 'MEMORY.md', 30, array(
-	'layer'       => MemoryFileRegistry::LAYER_AGENT,
-	'protected'   => true,
-	'modes'       => array( 'chat', 'pipeline' ),
-	'label'       => 'Agent Memory',
-	'description' => 'Accumulated knowledge. Injected in interactive modes only.',
-) );
-
-// User layer — human preferences, network-scoped on multisite.
-// Only injected in interactive modes where a human is present.
-// Pipelines can still opt in via pipeline memory file selection.
-MemoryFileRegistry::register( 'USER.md', 25, array(
-	'layer'       => MemoryFileRegistry::LAYER_USER,
-	'protected'   => true,
-	'modes'       => array( 'chat', 'editor' ),
-	'label'       => 'User Profile',
-	'description' => 'Information about the human the agent works with. Injected in chat and editor modes only.',
-) );
+function datamachine_register_default_memory_files(): void {
+	// Shared layer — site-wide context, visible to all agents.
+	// Composable: content assembled from sections registered against SectionRegistry
+	// (see inc/migrations/site-md.php). `editable` is forced to false by composable=true.
+	MemoryFileRegistry::register( 'SITE.md', 10, array(
+		'layer'       => MemoryFileRegistry::LAYER_SHARED,
+		'protected'   => true,
+		'composable'  => true,
+		'modes'       => array( MemoryFileRegistry::MODE_ALL ),
+		'label'       => 'Site Context',
+		'description' => 'Auto-generated site context. Composable — extend via SectionRegistry.',
+	) );
+	MemoryFileRegistry::register( 'RULES.md', 15, array(
+		'layer'       => MemoryFileRegistry::LAYER_SHARED,
+		'protected'   => true,
+		'editable'    => 'manage_options',
+		'modes'       => array( MemoryFileRegistry::MODE_ALL ),
+		'label'       => 'Site Rules',
+		'description' => 'Behavioral constraints that apply to every agent. Admin-editable.',
+	) );
+
+	// Agent layer — identity and knowledge, scoped to a single agent.
+	// Injected in interactive modes only (chat, pipeline). Excluded from
+	// system mode so autonomous maintenance tasks (e.g. daily memory
+	// compaction) are not primed with the agent's identity while operating
+	// on these files.
+	MemoryFileRegistry::register( 'SOUL.md', 20, array(
+		'layer'       => MemoryFileRegistry::LAYER_AGENT,
+		'protected'   => true,
+		'modes'       => array( 'chat', 'pipeline' ),
+		'label'       => 'Agent Identity',
+		'description' => 'Agent identity, voice, rules. Injected in interactive modes only.',
+	) );
+	MemoryFileRegistry::register( 'MEMORY.md', 30, array(
+		'layer'       => MemoryFileRegistry::LAYER_AGENT,
+		'protected'   => true,
+		'modes'       => array( 'chat', 'pipeline' ),
+		'label'       => 'Agent Memory',
+		'description' => 'Accumulated knowledge. Injected in interactive modes only.',
+	) );
+
+	// User layer — human preferences, network-scoped on multisite.
+	// Only injected in interactive modes where a human is present.
+	// Pipelines can still opt in via pipeline memory file selection.
+	MemoryFileRegistry::register( 'USER.md', 25, array(
+		'layer'       => MemoryFileRegistry::LAYER_USER,
+		'protected'   => true,
+		'modes'       => array( 'chat', 'editor' ),
+		'label'       => 'User Profile',
+		'description' => 'Information about the human the agent works with. Injected in chat and editor modes only.',
+	) );
+
+	// Network layer — multisite topology, only meaningful on multisite installs.
+	// Composable: content assembled from sections registered against SectionRegistry.
+	MemoryFileRegistry::register( 'NETWORK.md', 5, array(
+		'layer'       => MemoryFileRegistry::LAYER_NETWORK,
+		'protected'   => true,
+		'composable'  => true,
+		'modes'       => array( MemoryFileRegistry::MODE_ALL ),
+		'label'       => 'Network Context',
+		'description' => 'Auto-generated multisite network topology. Composable — extend via SectionRegistry.',
+	) );
+}
 
-// Network layer — multisite topology, only meaningful on multisite installs.
-// Composable: content assembled from sections registered against SectionRegistry.
-MemoryFileRegistry::register( 'NETWORK.md', 5, array(
-	'layer'       => MemoryFileRegistry::LAYER_NETWORK,
-	'protected'   => true,
-	'composable'  => true,
-	'modes'       => array( MemoryFileRegistry::MODE_ALL ),
-	'label'       => 'Network Context',
-	'description' => 'Auto-generated multisite network topology. Composable — extend via SectionRegistry.',
-) );
+if ( did_action( 'plugins_loaded' ) ) {
+	datamachine_register_default_memory_files();
+} else {
+	add_action( 'plugins_loaded', 'datamachine_register_default_memory_files', 0 );
+}
 
 // Composable file auto-regeneration — rebuilds AGENTS.md, SITE.md, NETWORK.md, and any other
 // composable files on plugin (de)activation plus any hooks plugins register via
diff --git a/tests/Unit/Core/Database/Chat/InMemoryConversationStore.php b/tests/Unit/Core/Database/Chat/InMemoryConversationStore.php
index ca41b47f7..b2405e65f 100644
--- a/tests/Unit/Core/Database/Chat/InMemoryConversationStore.php
+++ b/tests/Unit/Core/Database/Chat/InMemoryConversationStore.php
@@ -133,6 +133,35 @@ public function get_session( string $session_id ): ?array {
 		return $session;
 	}
 
+	public function list_sessions( WP_Agent_Workspace_Scope $workspace, int $user_id, array $args = array() ): array {
+		$include_messages = (bool) ( $args['include_messages'] ?? true );
+		$limit            = max( 1, min( 100, (int) ( $args['limit'] ?? 20 ) ) );
+		$offset           = max( 0, (int) ( $args['offset'] ?? 0 ) );
+		$rows             = array();
+
+		foreach ( $this->sessions as $session ) {
+			if ( $session['workspace_type'] !== $workspace->workspace_type || $session['workspace_id'] !== $workspace->workspace_id || (int) $session['user_id'] !== $user_id ) {
+				continue;
+			}
+			if ( is_string( $args['context'] ?? null ) && '' !== $args['context'] && $session['context'] !== $args['context'] ) {
+				continue;
+			}
+			if ( is_string( $args['agent_slug'] ?? null ) && '' !== $args['agent_slug'] && ( $session['agent_slug'] ?? '' ) !== sanitize_title( $args['agent_slug'] ) ) {
+				continue;
+			}
+
+			$row = $session;
+			if ( ! $include_messages ) {
+				unset( $row['messages'] );
+			}
+			$rows[] = $row;
+		}
+
+		usort( $rows, static fn( $a, $b ) => strcmp( $b['updated_at'], $a['updated_at'] ) );
+
+		return array_slice( $rows, $offset, $limit );
+	}
+
 	public function update_session( string $session_id, array $messages, array $metadata = array(), string $provider = '', string $model = '', ?string $provider_response_id = null ): bool {
 		if ( ! isset( $this->sessions[ $session_id ] ) ) {
 			return false;
diff --git a/tests/ai-request-metadata-guardrails-smoke.php b/tests/ai-request-metadata-guardrails-smoke.php
index a9a180119..0a311b09b 100644
--- a/tests/ai-request-metadata-guardrails-smoke.php
+++ b/tests/ai-request-metadata-guardrails-smoke.php
@@ -134,6 +134,7 @@ public function create_session( ...$args ): string {
 	}
 
 	public function get_session( string $session_id ): ?array { return null; }
+	public function list_sessions( WP_Agent_Workspace_Scope $workspace, int $user_id, array $args = array() ): array { return array(); }
 	public function update_session( string $session_id, array $messages, array $metadata = array(), string $provider = '', string $model = '', ?string $provider_response_id = null ): bool {
 		unset( $provider_response_id );
 		$this->updated[ $session_id ] = compact( 'messages', 'metadata', 'provider', 'model' );