diff --git a/php-transformer/src/ArtifactCompiler/ArtifactNormalizer.php b/php-transformer/src/ArtifactCompiler/ArtifactNormalizer.php
index fb0e1547..559ca15f 100644
--- a/php-transformer/src/ArtifactCompiler/ArtifactNormalizer.php
+++ b/php-transformer/src/ArtifactCompiler/ArtifactNormalizer.php
@@ -99,14 +99,15 @@ public function normalize(array $artifact): array
             $seenPaths[$path] = true;
             $mimeType = $this->mimeType((string) ($file['mime_type'] ?? $file['mime'] ?? $file['media_type'] ?? (str_contains((string) ($file['type'] ?? ''), '/') ? $file['type'] : '')), $path);
             $kind = $this->kind((string) ($file['kind'] ?? $file['type'] ?? ''), $path, $payload['content'], $mimeType);
-            $role = $this->role((string) ($file['role'] ?? ''), $kind, $mimeType, $path);
+            $declaredRole = $this->sanitizeKey((string) ($file['role'] ?? ''));
+            $role = $this->role($declaredRole, $kind, $mimeType, $path);
             $intent = $this->intent((string) ($file['intent'] ?? ''), $kind, $role);
             $binary = $payload['binary'] || ( ! $this->isTextKind($kind) && $this->isBinaryMimeType($mimeType) );
             $contentBase64 = $payload['content_base64'];
             if ( $binary && '' === $contentBase64 ) {
                 $contentBase64 = base64_encode($payload['content']);
             }
-            $entrypoint = in_array($path, $safeEntrypoints, true) || ! empty($file['entrypoint']) || 'entry' === $role;
+            $entrypoint = in_array($path, $safeEntrypoints, true) || ! empty($file['entrypoint']) || 'entry' === $declaredRole;
             if ( $entrypoint && ! in_array($path, $safeEntrypoints, true) ) {
                 $safeEntrypoints[] = $path;
             }
diff --git a/php-transformer/src/StaticSite/MaterializationPlanBuilder.php b/php-transformer/src/StaticSite/MaterializationPlanBuilder.php
index ca84e49a..76b0fe1a 100644
--- a/php-transformer/src/StaticSite/MaterializationPlanBuilder.php
+++ b/php-transformer/src/StaticSite/MaterializationPlanBuilder.php
@@ -37,7 +37,7 @@ public function fromCompiledSite(array $compiledSite): array
         $templateParts = $this->templateParts((array) ($compiledSite['template_parts'] ?? array()));
         $assets = $this->assets((array) ($compiledSite['assets'] ?? array()));
         $visualRepair = is_array($compiledSite['visual_repair'] ?? null) ? $compiledSite['visual_repair'] : array();
-        $routes = $this->routes($pages);
+        $routes = $this->routes($pages, (string) ($compiledSite['entry_path'] ?? ''));
         $navigationLinks = $this->navigationLinks($pages, $templateParts, $routes);
         $menus = $this->menus($navigationLinks);
         $assetRewriteCandidates = $this->assetRewriteCandidates($pages, $templateParts, $assets);
@@ -119,9 +119,10 @@ private function pages(array $pages): array
 
     /**
      * @param array<int,array<string,mixed>> $pages
+     * @param string $entryPath
      * @return array<int,array<string,mixed>>
      */
-    private function routes(array $pages): array
+    private function routes(array $pages, string $entryPath = ''): array
     {
         $routes = array();
         foreach ( $pages as $index => $page ) {
@@ -134,7 +135,7 @@ private function routes(array $pages): array
             $routes[] = array_filter(array(
                 'kind'        => 'route',
                 'source_path' => $sourcePath,
-                'target_path' => $this->routePath($page),
+                'target_path' => $this->routePath($page, $entryPath),
                 'target_slug' => $targetSlug,
                 'title'       => (string) ($page['title'] ?? ''),
                 'parent_source_path' => (string) (($page['metadata']['parent_source_path'] ?? '') ?: ''),
@@ -392,13 +393,23 @@ private function assetRewriteCandidates(array $pages, array $templateParts, arra
     /**
      * @param array<string,mixed> $page
      */
-    private function routePath(array $page): string
+    private function routePath(array $page, string $entryPath = ''): string
     {
         $sourcePath = (string) ($page['source_path'] ?? '');
         $slug = (string) ($page['slug'] ?? '');
-        if ( ! empty($page['entrypoint']) || preg_match('#(^|/)index\.[A-Za-z0-9]+$#', $sourcePath) ) {
+        if ( ! empty($page['entrypoint']) ) {
             return '/';
         }
+        if ( preg_match('#(^|/)index\.[A-Za-z0-9]+$#', $sourcePath) ) {
+            $directory = trim((string) pathinfo($sourcePath, PATHINFO_DIRNAME), '.');
+            $entryDirectory = trim((string) pathinfo($entryPath, PATHINFO_DIRNAME), '.');
+            if ( '' !== $entryDirectory && str_starts_with($directory . '/', $entryDirectory . '/') ) {
+                $directory = substr($directory, strlen($entryDirectory) + 1);
+            }
+            if ( '' !== $directory ) {
+                return '/' . trim($directory, '/');
+            }
+        }
 
         return '/' . trim('' !== $slug ? $slug : $this->slugFromPath($sourcePath), '/');
     }
diff --git a/php-transformer/tests/contract/wordpress-site-plan.php b/php-transformer/tests/contract/wordpress-site-plan.php
index 05c5d241..36a171e7 100644
--- a/php-transformer/tests/contract/wordpress-site-plan.php
+++ b/php-transformer/tests/contract/wordpress-site-plan.php
@@ -235,6 +235,13 @@
 $packagedPages = array(); foreach ($packagedRoutes['pages'] as $page) $packagedPages[$page['source_path']] = $page;
 $packagedCreates = array(); foreach ($packagedRoutes['operations'] as $operation) if ('create_page' === ($operation['kind'] ?? null)) $packagedCreates[$operation['source_path']] = $operation;
 $assert('/' === ($packagedPages['website/index.html']['route']['path'] ?? null) && '/contact' === ($packagedPages['website/contact.html']['route']['path'] ?? null) && '' === ($packagedPages['website/contact.html']['parent_source_path'] ?? null) && '/contact' === ($packagedCreates['website/contact.html']['route_path'] ?? null) && str_contains((string) ($packagedPages['website/index.html']['canonical_block_markup'] ?? ''), 'href="/contact"'), 'The entrypoint directory is an artifact packaging root for routes and root-relative document links, not a public route segment or phantom page parent.');
+$nestedEntrypointLast = (new ArtifactCompiler())->compile(array('entrypoint' => 'website/index.html', 'files' => array(array('path' => 'website/api/index.html', 'content' => '<main>API</main>'), array('path' => 'website/guides/index.html', 'content' => '<main>Guides</main>'), array('path' => 'website/index.html', 'content' => '<main>Home</main>'))))->toArray();
+$nestedEntrypointLastPlan = $nestedEntrypointLast['source_reports']['materialization_plan'] ?? array();
+$nestedEntrypointLastPages = array(); foreach ($nestedEntrypointLastPlan['pages'] ?? array() as $page) $nestedEntrypointLastPages[$page['source_path']] = $page;
+$nestedEntrypointLastRoutes = array(); foreach ($nestedEntrypointLastPlan['routes'] ?? array() as $route) $nestedEntrypointLastRoutes[$route['source_path']] = $route['target_path'];
+$assert('website/index.html' === ($nestedEntrypointLast['source_reports']['artifact']['entry_path'] ?? null) && array('website/index.html') === ($nestedEntrypointLast['source_reports']['artifact']['entrypoints'] ?? null) && true === ($nestedEntrypointLastPages['website/index.html']['entrypoint'] ?? null) && false === ($nestedEntrypointLastPages['website/api/index.html']['entrypoint'] ?? null) && false === ($nestedEntrypointLastPages['website/guides/index.html']['entrypoint'] ?? null) && 'entry' === ($nestedEntrypointLastPages['website/api/index.html']['metadata']['role'] ?? null) && 'entry' === ($nestedEntrypointLastPages['website/guides/index.html']['metadata']['role'] ?? null) && '/' === ($nestedEntrypointLastRoutes['website/index.html'] ?? null) && '/api' === ($nestedEntrypointLastRoutes['website/api/index.html'] ?? null) && '/guides' === ($nestedEntrypointLastRoutes['website/guides/index.html'] ?? null), 'Artifact-declared entrypoints remain authoritative when ordered last; inferred nested index roles remain documents with distinct materialization routes.');
+$explicitFileEntrypoint = (new ArtifactCompiler())->compile(array('files' => array(array('path' => 'website/index.html', 'content' => '<main>Home</main>'), array('path' => 'website/admin.html', 'content' => '<main>Admin</main>', 'entrypoint' => true), array('path' => 'website/preview.html', 'content' => '<main>Preview</main>', 'role' => 'entry'))))->toArray();
+$assert(array('website/admin.html', 'website/preview.html') === ($explicitFileEntrypoint['source_reports']['artifact']['entrypoints'] ?? null), 'Explicit per-file entrypoint flags and entry roles remain supported without an artifact-level declaration.');
 $outsidePackagedRoot = (new ArtifactCompiler())->compile(array('entrypoint' => 'website/index.html', 'files' => array('website/index.html' => '<main>Home</main>', 'other/contact.html' => '<main>Outside</main>')))->toArray();
 $assert(isset($outsidePackagedRoot['source_reports']['wordpress_site_plan_diagnostics']), 'HTML documents outside a nested entrypoint content root fail closed instead of leaking into public routes.');
 $forgedSyntheticPage = $packagedRoutes; foreach ($forgedSyntheticPage['pages'] as &$page) if ('website/contact.html' === ($page['source_path'] ?? null)) $page['synthetic'] = true; unset($page);