diff --git a/src/GenerateUri/FromProcessedConfiguration.php b/src/GenerateUri/FromProcessedConfiguration.php
index aae03b1..381987c 100644
--- a/src/GenerateUri/FromProcessedConfiguration.php
+++ b/src/GenerateUri/FromProcessedConfiguration.php
@@ -8,6 +8,7 @@
 
 use function array_key_exists;
 use function array_keys;
+use function array_reverse;
 use function assert;
 use function count;
 use function is_string;
@@ -34,7 +35,7 @@ public function forRoute(string $name, array $substitutions = []): string
 
         $missingParameters = [];
 
-        foreach ($this->processedConfiguration[$name] as $parsedRoute) {
+        foreach (array_reverse($this->processedConfiguration[$name]) as $parsedRoute) {
             $missingParameters = $this->missingParameters($parsedRoute, $substitutions);
 
             // Only attempt to generate the path if we have the necessary info
diff --git a/src/RouteCollector.php b/src/RouteCollector.php
index 9de94b6..3cd9bb9 100644
--- a/src/RouteCollector.php
+++ b/src/RouteCollector.php
@@ -31,7 +31,7 @@ public function __construct(
     public function addRoute(string|array $httpMethod, string $route, mixed $handler, array $extraParameters = []): void
     {
         $route = $this->currentGroupPrefix . $route;
-        $parsedRoutes = $this->routeParser->parse($route);
+        $parsedRoutes = array_reverse($this->routeParser->parse($route));
 
         $extraParameters = [self::ROUTE_REGEX => $route] + $extraParameters;
 
diff --git a/test/Dispatcher/DispatcherTestCase.php b/test/Dispatcher/DispatcherTestCase.php
index ba45688..dfbd86b 100644
--- a/test/Dispatcher/DispatcherTestCase.php
+++ b/test/Dispatcher/DispatcherTestCase.php
@@ -329,6 +329,18 @@ public static function provideFoundDispatchCases(): iterable
         };
 
         yield 'options method is supported' => ['OPTIONS', '/about', $callback, 'handler0', [], ['_route' => '/about']];
+
+        $callback = static function (ConfigureRoutes $r): void {
+            $r->addRoute('GET', '/about[/{aboutwhat}[/location]]', 'handler0');
+        };
+
+        yield 'Paths can be placed after an optional placeholder' => ['GET', '/about/some/location', $callback, 'handler0', ['aboutwhat' => 'some'], ['_route' => '/about[/{aboutwhat}[/location]]']];
+
+        $callback = static function (ConfigureRoutes $r): void {
+            $r->addRoute('GET', '/about[/{aboutwhat:.*}[/location]]', 'handler0');
+        };
+
+        yield 'Paths can be placed after an unlimited optional placeholder' => ['GET', '/about/the/nested/location', $callback, 'handler0', ['aboutwhat' => 'the/nested'], ['_route' => '/about[/{aboutwhat:.*}[/location]]']];
     }
 
     /** @return iterable<string, array{string, string, Closure(ConfigureRoutes):void}> */
diff --git a/test/GenerateUri/FromProcessedConfigurationTest.php b/test/GenerateUri/FromProcessedConfigurationTest.php
index 704b8ab..63fbb0f 100644
--- a/test/GenerateUri/FromProcessedConfigurationTest.php
+++ b/test/GenerateUri/FromProcessedConfigurationTest.php
@@ -9,7 +9,6 @@
 use PHPUnit\Framework\TestCase;
 
 use function array_map;
-use function array_reverse;
 
 /** @phpstan-import-type ParsedRoutes from RouteParser */
 final class FromProcessedConfigurationTest extends TestCase
@@ -129,7 +128,7 @@ public function unicodeParametersAreAlsoAccepted(): void
     private static function routeGeneratorFor(array $routeMap): GenerateUri
     {
         $parseRoutes = static function (string $route): array {
-            return array_reverse((new RouteParser\Std())->parse($route));
+            return (new RouteParser\Std())->parse($route);
         };
 
         return new GenerateUri\FromProcessedConfiguration(array_map($parseRoutes, $routeMap));
diff --git a/test/RouteCollectorTest.php b/test/RouteCollectorTest.php
index 4dd52ce..5d36022 100644
--- a/test/RouteCollectorTest.php
+++ b/test/RouteCollectorTest.php
@@ -118,6 +118,26 @@ public function routesCanBeGrouped(): void
         self::assertSame($expected, $dataGenerator->routes);
     }
 
+    #[PHPUnit\Test]
+    public function optionalRoutesCanBeUsed(): void
+    {
+        $dataGenerator = self::dummyNestedDataGenerator();
+        $r = new RouteCollector(new Std(), $dataGenerator);
+
+        $r->any('/any[/{optional}]', 'optional');
+        $r->get('/any[/{optional}/hello]', 'optional');
+
+        $expected = [
+            ['*', ['/any/', ['optional', '[^/]+']], 'optional', ['_route' => '/any[/{optional}]']],
+            ['*', ['/any'], 'optional', ['_route' => '/any[/{optional}]']],
+            ['GET', ['/any/', ['optional', '[^/]+'], '/hello'], 'optional', ['_route' => '/any[/{optional}/hello]']],
+            ['GET', ['/any'], 'optional', ['_route' => '/any[/{optional}/hello]']],
+        ];
+
+        self::assertObjectHasProperty('routes', $dataGenerator);
+        self::assertSame($expected, $dataGenerator->routes);
+    }
+
     #[PHPUnit\Test]
     public function namedRoutesShouldBeRegistered(): void
     {
@@ -180,4 +200,35 @@ public function addRoute(string $httpMethod, array $routeData, mixed $handler, a
             }
         };
     }
+
+    private static function dummyNestedDataGenerator(): DataGenerator
+    {
+        return new class implements DataGenerator
+        {
+            /** @var list<array{string, array<string|array{string, string}>, mixed, array<string, bool|float|int|string>}> */
+            public array $routes = [];
+
+            /** @inheritDoc */
+            public function getData(): array
+            {
+                return [[], []];
+            }
+
+            /** @inheritDoc */
+            public function addRoute(string $httpMethod, array $routeData, mixed $handler, array $extraParameters = []): void
+            {
+                $route = [$httpMethod];
+
+                $subroute = [];
+                foreach ($routeData as $data) {
+                    $subroute[] = $data;
+                }
+                $route[] = $subroute;
+
+                $route[] = $handler;
+                $route[] = $extraParameters;
+                $this->routes[] = $route;
+            }
+        };
+    }
 }