diff --git a/includes/Checker/Abstract_Check_Runner.php b/includes/Checker/Abstract_Check_Runner.php
index 8cb612c5b..c621088cc 100644
--- a/includes/Checker/Abstract_Check_Runner.php
+++ b/includes/Checker/Abstract_Check_Runner.php
@@ -541,6 +541,8 @@ private function get_check_exclude_slugs() {
 	 * @since 1.0.0
 	 *
 	 * @return string The plugin basename to check.
+	 *
+	 * @throws Exception Thrown if an plugin basename could not be set.
 	 */
 	final public function get_plugin_basename() {
 		if ( null === $this->plugin_basename ) {
@@ -550,10 +552,16 @@ final public function get_plugin_basename() {
 				$this->plugin_basename = Plugin_Request_Utility::download_plugin( $plugin );
 
 				$this->delete_plugin_folder = true;
-			} elseif ( Plugin_Request_Utility::is_directory_valid_plugin( $plugin ) ) {
-				$this->plugin_basename = $plugin;
 			} else {
-				$this->plugin_basename = Plugin_Request_Utility::get_plugin_basename_from_input( $plugin );
+				try {
+					$this->plugin_basename = Plugin_Request_Utility::get_plugin_basename_from_input( $plugin );
+				} catch ( Exception $exception ) {
+					if ( Plugin_Request_Utility::is_directory_valid_plugin( $plugin ) ) {
+						$this->plugin_basename = $plugin;
+					} else {
+						throw $exception;
+					}
+				}
 			}
 		}
 
diff --git a/includes/Plugin_Context.php b/includes/Plugin_Context.php
index e0c4923a8..cb5eafd9e 100644
--- a/includes/Plugin_Context.php
+++ b/includes/Plugin_Context.php
@@ -67,6 +67,8 @@ public function __construct( $main_file ) {
 				}
 			}
 		}
+
+		$this->main_file = $this->main_file;
 	}
 
 	/**
@@ -101,9 +103,9 @@ public function main_file() {
 	 */
 	public function path( $relative_path = '/' ) {
 		if ( is_dir( $this->main_file ) ) {
-			return trailingslashit( $this->main_file ) . ltrim( $relative_path, '/' );
+			return realpath( trailingslashit( $this->main_file ) . ltrim( $relative_path, '/' ) ) . '/';
 		} else {
-			return plugin_dir_path( $this->main_file ) . ltrim( $relative_path, '/' );
+			return realpath( plugin_dir_path( $this->main_file ) . ltrim( $relative_path, '/' ) ) . '/';
 		}
 	}
 
diff --git a/tests/behat/features/plugin-check-remote.feature b/tests/behat/features/plugin-check-remote.feature
index 6499f0663..4f1040a61 100644
--- a/tests/behat/features/plugin-check-remote.feature
+++ b/tests/behat/features/plugin-check-remote.feature
@@ -35,6 +35,10 @@ Feature: Test that the WP-CLI plugin check command works with remote ZIP url.
   Scenario: Test with valid ZIP
     When I run the WP-CLI command `plugin check https://github.com/WordPress/plugin-check/raw/trunk/tests/behat/testdata/foo-bar-wp.zip --fields=code,type --format=csv`
     Then STDOUT should contain:
+      """
+      FILE: foo-bar-wp.php
+      """
+    And STDOUT should contain:
       """
       WordPress.WP.AlternativeFunctions.rand_mt_rand,ERROR
       """
diff --git a/tests/behat/features/plugin-check-severity.feature b/tests/behat/features/plugin-check-severity.feature
index 38323ae62..bf86f9f28 100644
--- a/tests/behat/features/plugin-check-severity.feature
+++ b/tests/behat/features/plugin-check-severity.feature
@@ -64,6 +64,10 @@ Feature: Test that the severity level in plugin check works.
 
     When I run the WP-CLI command `plugin check foo-bar-wp --format=csv --fields=code,type,severity`
     Then STDOUT should contain:
+      """
+      FILE: foo-bar-wp.php
+      """
+    And STDOUT should contain:
       """
       allow_unfiltered_uploads_detected,ERROR,7
       """
diff --git a/tests/phpunit/testdata/plugins/test-plugin/test-plugin.php b/tests/phpunit/testdata/plugins/test-plugin/test-plugin.php
new file mode 100644
index 000000000..2d88c1458
--- /dev/null
+++ b/tests/phpunit/testdata/plugins/test-plugin/test-plugin.php
@@ -0,0 +1,16 @@
+<?php
+/**
+ * Plugin Name: Test Plugin
+ * Plugin URI: https://github.com/WordPress/plugin-check
+ * Description: Some plugin description.
+ * Requires at least: 6.0
+ * Requires PHP: 5.6
+ * Version: 1.0.0
+ * Author: WordPress Performance Team
+ * Author URI: https://make.wordpress.org/performance/
+ * License: GPLv2 or later
+ * License URI: https://www.gnu.org/licenses/old-licenses/gpl-2.0.html
+ * Text Domain: test-plugin
+ *
+ * @package test-plugin
+ */
diff --git a/tests/phpunit/tests/Checker/Check_Context_Tests.php b/tests/phpunit/tests/Checker/Check_Context_Tests.php
index ad6046d5b..17dc4e874 100644
--- a/tests/phpunit/tests/Checker/Check_Context_Tests.php
+++ b/tests/phpunit/tests/Checker/Check_Context_Tests.php
@@ -34,7 +34,7 @@ public function test_path() {
 	}
 
 	public function test_path_with_parameter() {
-		$this->assertSame( WP_PLUGIN_DIR . '/' . $this->plugin_name . '/another/folder', $this->check_context->path( '/another/folder' ) );
+		$this->assertSame( WP_PLUGIN_DIR . '/' . $this->plugin_name . '/test-content/themes', $this->check_context->path( '/test-content/themes' ) );
 	}
 
 	public function test_url() {
@@ -42,6 +42,6 @@ public function test_url() {
 	}
 
 	public function test_url_with_parameter() {
-		$this->assertSame( WP_PLUGIN_URL . '/' . $this->plugin_name . '/folder/file.css', $this->check_context->url( '/folder/file.css' ) );
+		$this->assertSame( WP_PLUGIN_URL . '/' . $this->plugin_name . '/assets/js/plugin-check-admin.js', $this->check_context->url( '/assets/js/plugin-check-admin.js' ) );
 	}
 }
diff --git a/tests/phpunit/tests/Checker/Check_Result_Tests.php b/tests/phpunit/tests/Checker/Check_Result_Tests.php
index 3015eddc9..b8ca0799e 100644
--- a/tests/phpunit/tests/Checker/Check_Result_Tests.php
+++ b/tests/phpunit/tests/Checker/Check_Result_Tests.php
@@ -19,7 +19,7 @@ class Check_Result_Tests extends WP_UnitTestCase {
 	public function set_up() {
 		parent::set_up();
 
-		$check_context = new Check_Context( 'test-plugin/test-plugin.php' );
+		$check_context = new Check_Context( UNIT_TESTS_PLUGIN_DIR . 'test-plugin/test-plugin.php' );
 
 		$this->check_result = new Check_Result( $check_context );
 	}
@@ -28,7 +28,7 @@ public function test_plugin() {
 		$this->assertInstanceOf( Check_Context::class, $this->check_result->plugin() );
 
 		// Check the Check_Context has the correct basename.
-		$this->assertSame( 'test-plugin/test-plugin.php', $this->check_result->plugin()->basename() );
+		$this->assertStringEndsWith( 'test-plugin/test-plugin.php', $this->check_result->plugin()->basename() );
 	}
 
 	public function test_add_message_with_warning() {
@@ -37,7 +37,7 @@ public function test_add_message_with_warning() {
 			'Warning message',
 			array(
 				'code'   => 'test_warning',
-				'file'   => 'test-plugin/test-plugin.php',
+				'file'   => UNIT_TESTS_PLUGIN_DIR . 'test-plugin/test-plugin.php',
 				'line'   => 12,
 				'column' => 40,
 			)
@@ -73,7 +73,7 @@ public function test_add_message_with_error() {
 			'Error message',
 			array(
 				'code'   => 'test_error',
-				'file'   => 'test-plugin/test-plugin.php',
+				'file'   => UNIT_TESTS_PLUGIN_DIR . 'test-plugin/test-plugin.php',
 				'line'   => 22,
 				'column' => 30,
 			)
@@ -113,7 +113,7 @@ public function test_get_errors_with_errors() {
 			'Error message',
 			array(
 				'code'   => 'test_error',
-				'file'   => 'test-plugin/test-plugin.php',
+				'file'   => UNIT_TESTS_PLUGIN_DIR . 'test-plugin/test-plugin.php',
 				'line'   => 22,
 				'column' => 30,
 			)
@@ -146,7 +146,7 @@ public function test_get_warnings_with_warnings() {
 			'Warning message',
 			array(
 				'code'   => 'test_warning',
-				'file'   => 'test-plugin/test-plugin.php',
+				'file'   => UNIT_TESTS_PLUGIN_DIR . 'test-plugin/test-plugin.php',
 				'line'   => 22,
 				'column' => 30,
 			)
diff --git a/tests/phpunit/tests/Plugin_Context_Tests.php b/tests/phpunit/tests/Plugin_Context_Tests.php
index e930aecb0..db5f01a53 100644
--- a/tests/phpunit/tests/Plugin_Context_Tests.php
+++ b/tests/phpunit/tests/Plugin_Context_Tests.php
@@ -34,7 +34,7 @@ public function test_path() {
 	}
 
 	public function test_path_with_parameter() {
-		$this->assertSame( WP_PLUGIN_DIR . '/' . $this->plugin_name . '/another/folder', $this->plugin_context->path( '/another/folder' ) );
+		$this->assertSame( WP_PLUGIN_DIR . '/' . $this->plugin_name . '/test-content/themes', $this->plugin_context->path( '/test-content/themes' ) );
 	}
 
 	public function test_url() {
@@ -42,7 +42,7 @@ public function test_url() {
 	}
 
 	public function test_url_with_parameter() {
-		$this->assertSame( WP_PLUGIN_URL . '/' . $this->plugin_name . '/folder/file.css', $this->plugin_context->url( '/folder/file.css' ) );
+		$this->assertSame( WP_PLUGIN_URL . '/' . $this->plugin_name . '/assets/js/plugin-check-admin.js', $this->plugin_context->url( '/assets/js/plugin-check-admin.js' ) );
 	}
 
 	public function test_location() {