diff --git a/src/wp-includes/script-loader.php b/src/wp-includes/script-loader.php
index 0ea531824b..713a0d3118 100644
--- a/src/wp-includes/script-loader.php
+++ b/src/wp-includes/script-loader.php
@@ -2872,12 +2872,18 @@ function wp_maybe_inline_styles() {
 
 	// Build an array of styles that have a path defined.
 	foreach ( $wp_styles->queue as $handle ) {
-		if ( wp_styles()->get_data( $handle, 'path' ) && file_exists( $wp_styles->registered[ $handle ]->extra['path'] ) ) {
+		$src  = $wp_styles->registered[ $handle ]->src;
+		$path = wp_styles()->get_data( $handle, 'path' );
+		if ( $path && $src ) {
+			$size = wp_filesize( $path );
+			if ( ! $size ) {
+				continue;
+			}
 			$styles[] = array(
 				'handle' => $handle,
-				'src'    => $wp_styles->registered[ $handle ]->src,
-				'path'   => $wp_styles->registered[ $handle ]->extra['path'],
-				'size'   => filesize( $wp_styles->registered[ $handle ]->extra['path'] ),
+				'src'    => $src,
+				'path'   => $path,
+				'size'   => $size,
 			);
 		}
 	}
diff --git a/tests/phpunit/tests/dependencies/styles.php b/tests/phpunit/tests/dependencies/styles.php
index ad2e672dc0..798b75a252 100644
--- a/tests/phpunit/tests/dependencies/styles.php
+++ b/tests/phpunit/tests/dependencies/styles.php
@@ -517,4 +517,99 @@ CSS;
 			$GLOBALS['wp_styles']->registered['wp-block-library']->src
 		);
 	}
+
+	/**
+	 * @ticket 58394
+	 *
+	 * @covers ::wp_maybe_inline_styles
+	 */
+	public function test_wp_maybe_inline_styles() {
+		wp_register_style( 'test-handle', '/' . WPINC . '/css/classic-themes.css' );
+		wp_style_add_data( 'test-handle', 'path', ABSPATH . WPINC . '/css/classic-themes.css' );
+
+		wp_enqueue_style( 'test-handle' );
+
+		wp_maybe_inline_styles();
+
+		$this->assertFalse( $GLOBALS['wp_styles']->registered['test-handle']->src, 'Source of style should be reset to false' );
+
+		$css = file_get_contents( ABSPATH . WPINC . '/css/classic-themes.css' );
+		$this->assertSameSets( $GLOBALS['wp_styles']->registered['test-handle']->extra['after'], array( $css ), 'Source of style should set to after property' );
+	}
+
+	/**
+	 * wp_filesize should be only be called once, as on the second run of wp_maybe_inline_styles,
+	 * src will be set to false and filesize will not be requested.
+	 *
+	 * @ticket 58394
+	 *
+	 * @covers ::wp_maybe_inline_styles
+	 */
+	public function test_wp_maybe_inline_styles_multiple_runs() {
+		$filter = new MockAction();
+		add_filter( 'pre_wp_filesize', array( $filter, 'filter' ) );
+		wp_register_style( 'test-handle', '/' . WPINC . '/css/classic-themes.css' );
+		wp_style_add_data( 'test-handle', 'path', ABSPATH . WPINC . '/css/classic-themes.css' );
+
+		wp_enqueue_style( 'test-handle' );
+
+		wp_maybe_inline_styles();
+		wp_maybe_inline_styles();
+
+		$this->assertSame( 1, $filter->get_call_count() );
+	}
+
+	/**
+	 * @ticket 58394
+	 *
+	 * @covers ::wp_maybe_inline_styles
+	 */
+	public function test_test_wp_maybe_inline_styles_missing_file() {
+		$filter = new MockAction();
+		add_filter( 'pre_wp_filesize', array( $filter, 'filter' ) );
+		$url = '/' . WPINC . '/css/invalid.css';
+		wp_register_style( 'test-handle', $url );
+		wp_style_add_data( 'test-handle', 'path', ABSPATH . WPINC . '/css/invalid.css' );
+
+		wp_enqueue_style( 'test-handle' );
+
+		wp_maybe_inline_styles();
+
+		$this->assertSame( $GLOBALS['wp_styles']->registered['test-handle']->src, $url, 'Source should not change' );
+		$this->assertArrayNotHasKey( 'after', $GLOBALS['wp_styles']->registered['test-handle']->extra, 'Source of style not should set to after property' );
+		$this->assertSame( 1, $filter->get_call_count(), 'wp_filesize should only be called once' );
+	}
+
+	/**
+	 * @ticket 58394
+	 *
+	 * @covers ::wp_maybe_inline_styles
+	 */
+	public function test_wp_maybe_inline_styles_no_src() {
+		wp_register_style( 'test-handle', false );
+		wp_style_add_data( 'test-handle', 'path', ABSPATH . WPINC . '/css/classic-themes.css' );
+
+		wp_enqueue_style( 'test-handle' );
+
+		wp_maybe_inline_styles();
+
+		$this->assertFalse( $GLOBALS['wp_styles']->registered['test-handle']->src, 'Source of style should remain false' );
+		$this->assertArrayNotHasKey( 'after', $GLOBALS['wp_styles']->registered['test-handle']->extra, 'Source of style not should set to after property' );
+	}
+
+	/**
+	 * @ticket 58394
+	 *
+	 * @covers ::wp_maybe_inline_styles
+	 */
+	public function test_wp_maybe_inline_styles_no_path() {
+		$url = '/' . WPINC . '/css/classic-themes.css';
+		wp_register_style( 'test-handle', $url );
+
+		wp_enqueue_style( 'test-handle' );
+
+		wp_maybe_inline_styles();
+
+		$this->assertSame( $GLOBALS['wp_styles']->registered['test-handle']->src, $url );
+	}
 }