diff --git src/wp-admin/includes/schema.php src/wp-admin/includes/schema.php
index 296a699..634f9a8 100644
--- src/wp-admin/includes/schema.php
+++ src/wp-admin/includes/schema.php
@@ -397,7 +397,7 @@ function populate_options() {
 	'links_updated_date_format' => __('F j, Y g:i a'),
 	'comment_moderation' => 0,
 	'moderation_notify' => 1,
-	'permalink_structure' => '',
+	'permalink_structure' => '/%year%/%monthnum%/%day%/%postname%/',
 	'gzipcompression' => 0,
 	'hack_file' => 0,
 	'blog_charset' => 'UTF-8',
@@ -495,7 +495,6 @@ function populate_options() {
 	if ( is_multisite() ) {
 		/* translators: blog tagline */
 		$options[ 'blogdescription' ] = sprintf(__('Just another %s site'), get_current_site()->site_name );
-		$options[ 'permalink_structure' ] = '/%year%/%monthnum%/%day%/%postname%/';
 	}
 
 	// Set autoload to no for these options
diff --git src/wp-admin/includes/upgrade.php src/wp-admin/includes/upgrade.php
index b72303a..6912271 100644
--- src/wp-admin/includes/upgrade.php
+++ src/wp-admin/includes/upgrade.php
@@ -241,6 +241,23 @@ As a new WordPress user, you should go to <a href=\"%s\">your dashboard</a> to d
 	elseif ( ! is_super_admin( $user_id ) && ! metadata_exists( 'user', $user_id, 'show_welcome_panel' ) )
 		update_user_meta( $user_id, 'show_welcome_panel', 2 );
 
+	// Verify pretty permalinks work, and fall back to ugly permalinks if they do not.
+	if ( ! is_multisite() ) {
+		// Hard flush rules and force .htaccess or web.config file refresh.
+		$wp_rewrite->flush_rules( true );
+
+		// Send a HEAD request to the dummy post to smoke test pretty permalinks.
+		$dummy_link = get_permalink( 1 );
+		$dummy_response = wp_remote_head( $dummy_link );
+		$pretty_permalinks = isset( $dummy_response['response']['code'] ) && 200 == $dummy_response['response']['code']; 
+
+		// Fall back to ugly permalinks
+		if ( ! $pretty_permalinks ) {
+			$wp_rewrite->set_permalink_structure( '' );
+			$wp_rewrite->flush_rules();
+		}
+	}
+
 	if ( is_multisite() ) {
 		// Flush rules to pick up the new page.
 		$wp_rewrite->init();