diff --git a/includes/desktop-files/cascade-cleanup.php b/includes/desktop-files/cascade-cleanup.php
index 2ed8a8aae..dcec4c960 100644
--- a/includes/desktop-files/cascade-cleanup.php
+++ b/includes/desktop-files/cascade-cleanup.php
@@ -19,6 +19,8 @@
  *                            skips `wp_trash_post`.
  *   - `deleted_user`       — user account removed (with or without
  *                            content reassignment).
+ *   - `trashed_comment`    — comment moved to WP trash.
+ *   - `deleted_comment`    — comment hard-deleted.
  *
  * Implementation is a bulk UPDATE that bypasses the per-placement
  * permission check used by user-initiated trash. The trashing
@@ -232,3 +234,24 @@ function openstation_files_cascade_on_user_delete( $user_id ) {
 }
 
 add_action( 'deleted_user', 'openstation_files_cascade_on_user_delete', 10, 1 );
+
+/**
+ * Wrap a `(comment_id)` Core action so it cascades against
+ * `file_type='comment'`. Fires when a comment is trashed or
+ * permanently deleted so shortcuts pointing at it are soft-trashed.
+ *
+ * @param int $comment_id Comment id.
+ */
+function openstation_files_cascade_on_comment_trash( $comment_id ) {
+	$comment_id = (int) $comment_id;
+	if ( $comment_id <= 0 ) {
+		return;
+	}
+	openstation_files_cascade_trash_placements_for_entity(
+		'comment',
+		(string) $comment_id
+	);
+}
+
+add_action( 'trashed_comment', 'openstation_files_cascade_on_comment_trash', 10, 1 );
+add_action( 'deleted_comment', 'openstation_files_cascade_on_comment_trash', 10, 1 );
diff --git a/tests/phpunit/tests/desktopFilesCascadeCleanup.php b/tests/phpunit/tests/desktopFilesCascadeCleanup.php
index 0c44b7626..daa69b5af 100644
--- a/tests/phpunit/tests/desktopFilesCascadeCleanup.php
+++ b/tests/phpunit/tests/desktopFilesCascadeCleanup.php
@@ -1,7 +1,7 @@
 <?php
 /**
  * Tests for the cascade cleanup of placements when a source
- * entity (post, attachment, user) is trashed or deleted via any
+ * entity (post, attachment, user, comment) is trashed or deleted via any
  * WordPress route.
  *
  * @package WordPress
@@ -190,6 +190,38 @@ public function test_deleted_user_triggers_cascade() {
 		$this->assertNotNull( $this->read_trash_columns( $p_id )['trashed_at_ms'] );
 	}
 
+	/**
+	 * @covers ::openstation_files_cascade_on_comment_trash
+	 */
+	public function test_wp_trash_comment_triggers_cascade() {
+		$post_id    = self::factory()->post->create( array( 'post_status' => 'publish' ) );
+		$comment_id = self::factory()->comment->create( array( 'comment_post_ID' => $post_id ) );
+		$p_id       = openstation_files_place( self::$admin_id, 0, 'comment', (string) $comment_id, array( 'x' => 0, 'y' => 0 ) );
+
+		wp_trash_comment( $comment_id );
+
+		$this->assertNotNull(
+			$this->read_trash_columns( $p_id )['trashed_at_ms'],
+			'wp_trash_comment() must cascade-soft-trash the matching placement.'
+		);
+	}
+
+	/**
+	 * @covers ::openstation_files_cascade_on_comment_trash
+	 */
+	public function test_delete_comment_triggers_cascade() {
+		$post_id    = self::factory()->post->create( array( 'post_status' => 'publish' ) );
+		$comment_id = self::factory()->comment->create( array( 'comment_post_ID' => $post_id ) );
+		$p_id       = openstation_files_place( self::$admin_id, 0, 'comment', (string) $comment_id, array( 'x' => 0, 'y' => 0 ) );
+
+		wp_delete_comment( $comment_id, true );
+
+		$this->assertNotNull(
+			$this->read_trash_columns( $p_id )['trashed_at_ms'],
+			'wp_delete_comment() must cascade-soft-trash the matching placement.'
+		);
+	}
+
 	/**
 	 * @covers ::openstation_files_cascade_trash_placements_for_entity
 	 */