diff --git a/plugins/woocommerce/src/Internal/Admin/Logging/FileV2/File.php b/plugins/woocommerce/src/Internal/Admin/Logging/FileV2/File.php
index bd28a030fbc..386197ca274 100644
--- a/plugins/woocommerce/src/Internal/Admin/Logging/FileV2/File.php
+++ b/plugins/woocommerce/src/Internal/Admin/Logging/FileV2/File.php
@@ -89,6 +89,9 @@ class File {
 			}
 
 			$this->source = substr( $this->source, 0, $rotation_marker );
+			if ( count( $segments ) < 5 ) {
+				$this->hash = $this->source;
+			}
 		}
 	}
 
diff --git a/plugins/woocommerce/tests/php/src/Internal/Admin/Logging/FileV2/FileTest.php b/plugins/woocommerce/tests/php/src/Internal/Admin/Logging/FileV2/FileTest.php
new file mode 100644
index 00000000000..4e2a6e252fd
--- /dev/null
+++ b/plugins/woocommerce/tests/php/src/Internal/Admin/Logging/FileV2/FileTest.php
@@ -0,0 +1,110 @@
+<?php
+declare( strict_types = 1 );
+
+namespace Automattic\WooCommerce\Tests\Internal\Admin\Logging\FileV2;
+
+use Automattic\Jetpack\Constants;
+use Automattic\WooCommerce\Internal\Admin\Logging\FileV2\File;
+use WC_Unit_Test_Case;
+
+/**
+ * FileTest class.
+ */
+class FileTest extends WC_Unit_Test_Case {
+	/**
+	 * Tear down after each test.
+	 *
+	 * @return void
+	 */
+	public function tearDown(): void {
+		// Delete all created log files.
+		$files = glob( trailingslashit( realpath( Constants::get_constant( 'WC_LOG_DIR' ) ) ) . '*.log' );
+		foreach ( $files as $file ) {
+			@unlink( $file );
+		}
+
+		parent::tearDown();
+	}
+
+	/**
+	 * @testdox Check that all properties are populated correctly when a File instance receives a filename in the standard format.
+	 */
+	public function test_initialize_file_standard() {
+		$filename = Constants::get_constant( 'WC_LOG_DIR' ) . 'test-Source_1-1-2023-10-23-' . wp_hash( 'cheddar' ) . '.log';
+		$resource = fopen( $filename, 'a' ); // phpcs:ignore WordPress.PHP.NoSilencedErrors
+		fclose( $resource );
+		$file = new File( $filename );
+
+		$this->assertEquals( 'test-Source_1-1-2023-10-23-' . wp_hash( 'cheddar' ) . '.log', $file->get_basename() );
+		$this->assertEquals( 'test-Source_1-1', $file->get_source() );
+		$this->assertNull( $file->get_rotation() );
+		$this->assertEquals( strtotime( '2023-10-23' ), $file->get_created_timestamp() );
+		$this->assertEquals( wp_hash( 'cheddar' ), $file->get_hash() );
+	}
+
+	/**
+	 * @testdox Check that all properties are populated correctly when a File instance receives a rotated filename in the standard format.
+	 */
+	public function test_initialize_file_standard_rotated() {
+		$filename = Constants::get_constant( 'WC_LOG_DIR' ) . 'test-Source_1-1.3-2023-10-23-' . wp_hash( 'cheddar' ) . '.log';
+		$resource = fopen( $filename, 'a' ); // phpcs:ignore WordPress.PHP.NoSilencedErrors
+		fclose( $resource );
+		$file = new File( $filename );
+
+		$this->assertEquals( 'test-Source_1-1.3-2023-10-23-' . wp_hash( 'cheddar' ) . '.log', $file->get_basename() );
+		$this->assertEquals( 'test-Source_1-1', $file->get_source() );
+		$this->assertEquals( 3, $file->get_rotation() );
+		$this->assertEquals( strtotime( '2023-10-23' ), $file->get_created_timestamp() );
+		$this->assertEquals( wp_hash( 'cheddar' ), $file->get_hash() );
+	}
+
+	/**
+	 * @testdox Check that all properties are populated correctly when a File instance receives a filename in a non-standard format.
+	 */
+	public function test_initialize_file_non_standard() {
+		$filename = Constants::get_constant( 'WC_LOG_DIR' ) . 'test-Source_1-1-' . wp_hash( 'cheddar' ) . '.log';
+		$resource = fopen( $filename, 'a' ); // phpcs:ignore WordPress.PHP.NoSilencedErrors
+		fclose( $resource );
+		$file = new File( $filename );
+
+		$this->assertEquals( 'test-Source_1-1-' . wp_hash( 'cheddar' ) . '.log', $file->get_basename() );
+		$this->assertEquals( 'test-Source_1-1-' . wp_hash( 'cheddar' ), $file->get_source() );
+		$this->assertNull( $file->get_rotation() );
+		$this->assertEquals( filemtime( $filename ), $file->get_created_timestamp() );
+		$this->assertEquals( 'test-Source_1-1-' . wp_hash( 'cheddar' ), $file->get_hash() );
+	}
+
+	/**
+	 * @testdox Check that all properties are populated correctly when a File instance receives a rotated filename in a non-standard format.
+	 */
+	public function test_initialize_file_non_standard_rotated() {
+		$filename = Constants::get_constant( 'WC_LOG_DIR' ) . 'test-Source_1-1-' . wp_hash( 'cheddar' ) . '.5.log';
+		$resource = fopen( $filename, 'a' ); // phpcs:ignore WordPress.PHP.NoSilencedErrors
+		fclose( $resource );
+		$file = new File( $filename );
+
+		$this->assertEquals( 'test-Source_1-1-' . wp_hash( 'cheddar' ) . '.5.log', $file->get_basename() );
+		$this->assertEquals( 'test-Source_1-1-' . wp_hash( 'cheddar' ), $file->get_source() );
+		$this->assertEquals( 5, $file->get_rotation() );
+		$this->assertEquals( filemtime( $filename ), $file->get_created_timestamp() );
+		$this->assertEquals( 'test-Source_1-1-' . wp_hash( 'cheddar' ), $file->get_hash() );
+	}
+
+	/**
+	 * @testdox The delete method should delete the file from the filesystem.
+	 */
+	public function test_delete() {
+		$filename = Constants::get_constant( 'WC_LOG_DIR' ) . 'test-Source_1-1-' . wp_hash( 'cheddar' ) . '.5.log';
+		$resource = fopen( $filename, 'a' ); // phpcs:ignore WordPress.PHP.NoSilencedErrors
+		fclose( $resource );
+		$file = new File( $filename );
+
+		$files = glob( trailingslashit( realpath( Constants::get_constant( 'WC_LOG_DIR' ) ) ) . '*.log' );
+		$this->assertCount( 1, $files );
+
+		$file->delete();
+
+		$files = glob( trailingslashit( realpath( Constants::get_constant( 'WC_LOG_DIR' ) ) ) . '*.log' );
+		$this->assertCount( 0, $files );
+	}
+}