diff --git a/config/autoload/url-shortener.global.php b/config/autoload/url-shortener.global.php
index bdd257d5..bf9ecb93 100644
--- a/config/autoload/url-shortener.global.php
+++ b/config/autoload/url-shortener.global.php
@@ -23,6 +23,7 @@ return (static function (): array {
             'default_short_codes_length' => $shortCodesLength,
             'auto_resolve_titles' => (bool) EnvVars::AUTO_RESOLVE_TITLES->loadFromEnv(false),
             'append_extra_path' => (bool) EnvVars::REDIRECT_APPEND_EXTRA_PATH->loadFromEnv(false),
+            'multi_segment_slugs_enabled' => (bool) EnvVars::MULTI_SEGMENT_SLUGS_ENABLED->loadFromEnv(false),
         ],
 
     ];
diff --git a/module/Core/src/Options/UrlShortenerOptions.php b/module/Core/src/Options/UrlShortenerOptions.php
index 57f4bc37..ce4bc86d 100644
--- a/module/Core/src/Options/UrlShortenerOptions.php
+++ b/module/Core/src/Options/UrlShortenerOptions.php
@@ -12,6 +12,7 @@ class UrlShortenerOptions extends AbstractOptions
 
     private bool $autoResolveTitles = false;
     private bool $appendExtraPath = false;
+    private bool $multiSegmentSlugsEnabled = false;
 
     public function autoResolveTitles(): bool
     {
@@ -32,4 +33,14 @@ class UrlShortenerOptions extends AbstractOptions
     {
         $this->appendExtraPath = $appendExtraPath;
     }
+
+    public function multiSegmentSlugsEnabled(): bool
+    {
+        return $this->multiSegmentSlugsEnabled;
+    }
+
+    protected function setMultiSegmentSlugsEnabled(bool $multiSegmentSlugsEnabled): void
+    {
+        $this->multiSegmentSlugsEnabled = $multiSegmentSlugsEnabled;
+    }
 }
diff --git a/module/Core/src/ShortUrl/Middleware/ExtraPathRedirectMiddleware.php b/module/Core/src/ShortUrl/Middleware/ExtraPathRedirectMiddleware.php
index 2704cadb..44cab54c 100644
--- a/module/Core/src/ShortUrl/Middleware/ExtraPathRedirectMiddleware.php
+++ b/module/Core/src/ShortUrl/Middleware/ExtraPathRedirectMiddleware.php
@@ -38,9 +38,7 @@ class ExtraPathRedirectMiddleware implements MiddlewareInterface
     {
         /** @var NotFoundType|null $notFoundType */
         $notFoundType = $request->getAttribute(NotFoundType::class);
-
-        // This logic is applied only if actively opted in and current URL is potentially /{shortCode}/[...]
-        if (! $notFoundType?->isRegularNotFound() || ! $this->urlShortenerOptions->appendExtraPath()) {
+        if (! $this->shouldApplyLogic($notFoundType)) {
             return $handler->handle($request);
         }
 
@@ -61,6 +59,21 @@ class ExtraPathRedirectMiddleware implements MiddlewareInterface
         }
     }
 
+    private function shouldApplyLogic(?NotFoundType $notFoundType): bool
+    {
+        if ($notFoundType === null || ! $this->urlShortenerOptions->appendExtraPath()) {
+            return false;
+        }
+
+        return (
+            // If multi-segment slugs are enabled, the appropriate not-found type is "invalid_short_url"
+            $this->urlShortenerOptions->multiSegmentSlugsEnabled() && $notFoundType->isInvalidShortUrl()
+        ) || (
+            // If multi-segment slugs are disabled, the appropriate not-found type is "regular_404"
+            ! $this->urlShortenerOptions->multiSegmentSlugsEnabled() && $notFoundType->isRegularNotFound()
+        );
+    }
+
     /**
      * @return array{0: string, 1: string|null}
      */
diff --git a/module/Core/test/ShortUrl/Middleware/ExtraPathRedirectMiddlewareTest.php b/module/Core/test/ShortUrl/Middleware/ExtraPathRedirectMiddlewareTest.php
index d8997524..f4e31c5d 100644
--- a/module/Core/test/ShortUrl/Middleware/ExtraPathRedirectMiddlewareTest.php
+++ b/module/Core/test/ShortUrl/Middleware/ExtraPathRedirectMiddlewareTest.php
@@ -16,6 +16,7 @@ use Prophecy\Prophecy\ObjectProphecy;
 use Psr\Http\Message\ServerRequestInterface;
 use Psr\Http\Server\MiddlewareInterface;
 use Psr\Http\Server\RequestHandlerInterface;
+use Shlinkio\Shlink\Core\Action\RedirectAction;
 use Shlinkio\Shlink\Core\Entity\ShortUrl;
 use Shlinkio\Shlink\Core\ErrorHandler\Model\NotFoundType;
 use Shlinkio\Shlink\Core\Exception\ShortUrlNotFoundException;
@@ -65,9 +66,11 @@ class ExtraPathRedirectMiddlewareTest extends TestCase
      */
     public function handlerIsCalledWhenConfigPreventsRedirectWithExtraPath(
         bool $appendExtraPath,
+        bool $multiSegmentEnabled,
         ServerRequestInterface $request,
     ): void {
         $this->options->appendExtraPath = $appendExtraPath;
+        $this->options->multiSegmentSlugsEnabled = $multiSegmentEnabled;
 
         $this->middleware->process($request, $this->handler->reveal());
 
@@ -83,20 +86,30 @@ class ExtraPathRedirectMiddlewareTest extends TestCase
         $buildReq = static fn (?NotFoundType $type): ServerRequestInterface =>
             $baseReq->withAttribute(NotFoundType::class, $type);
 
-        yield 'disabled option' => [false, $buildReq(NotFoundType::fromRequest($baseReq, '/foo/bar'))];
-        yield 'base_url error' => [true, $buildReq(NotFoundType::fromRequest($baseReq, ''))];
+        yield 'disabled option' => [false, false, $buildReq(NotFoundType::fromRequest($baseReq, '/foo/bar'))];
+        yield 'no error type' => [true, false, $buildReq(null)];
+        yield 'base_url error' => [true, false, $buildReq(NotFoundType::fromRequest($baseReq, ''))];
         yield 'invalid_short_url error' => [
             true,
-            $buildReq(NotFoundType::fromRequest($baseReq, ''))->withAttribute(
+            false,
+            $buildReq(NotFoundType::fromRequest($baseReq->withUri(new Uri('/foo'))->withAttribute(
                 RouteResult::class,
                 RouteResult::fromRoute(new Route(
-                    '',
+                    '/foo',
                     $this->prophesize(MiddlewareInterface::class)->reveal(),
                     ['GET'],
+                    RedirectAction::class,
                 )),
-            ),
+            ), '')),
+        ];
+        yield 'regular_404 error with multi-segment slugs' => [
+            true,
+            true,
+            $buildReq(NotFoundType::fromRequest($baseReq->withUri(new Uri('/foo'))->withAttribute(
+                RouteResult::class,
+                RouteResult::fromRouteFailure(['GET']),
+            ), '')),
         ];
-        yield 'no error type' => [true, $buildReq(null)];
     }
 
     /** @test */