diff --git a/Classes/Utility/UrlUtility.php b/Classes/Utility/UrlUtility.php
index ccaf2d32..c8b7ad50 100644
--- a/Classes/Utility/UrlUtility.php
+++ b/Classes/Utility/UrlUtility.php
@@ -12,6 +12,7 @@
 namespace FriendsOfTYPO3\Headless\Utility;
 
 use Psr\Http\Message\ServerRequestInterface;
+use Psr\Http\Message\UriInterface;
 use Psr\Log\LoggerAwareInterface;
 use Psr\Log\LoggerAwareTrait;
 use Symfony\Component\ExpressionLanguage\SyntaxError;
@@ -29,6 +30,8 @@
 use function ltrim;
 use function rtrim;
 use function str_contains;
+use function strlen;
+use function substr;
 
 class UrlUtility implements LoggerAwareInterface, HeadlessFrontendUrlInterface
 {
@@ -83,8 +86,6 @@ public function getFrontendUrlWithSite($url, SiteInterface $site, string $return
         }
 
         try {
-            $base = $site->getBase()->getHost();
-            $port = $site->getBase()->getPort();
             $frontendBaseUrl = $this->resolveWithVariants(
                 $this->conf[$returnField] ?? '',
                 $this->variants,
@@ -101,14 +102,14 @@ public function getFrontendUrlWithSite($url, SiteInterface $site, string $return
             $frontPort = $frontendBase->getPort();
             $targetUri = new Uri($this->sanitizeBaseUrl($url));
 
-            if (str_contains($url, $base)) {
+            if (str_contains($url, $site->getBase()->getHost())) {
                 $targetUri = $targetUri->withHost($frontBase);
                 if ($frontExtraPath) {
-                    $targetUri = $targetUri->withPath($frontExtraPath . ($targetUri->getPath() !== '' ? '/' . ltrim($targetUri->getPath(), '/') : ''));
+                    $targetUri = $targetUri->withPath($this->handleFrontendAndBackendPaths($frontExtraPath, $targetUri, $site->getBase()->getPath()));
                 }
             }
 
-            if ($port === $frontPort) {
+            if ($site->getBase()->getPort() === $frontPort) {
                 return (string)$targetUri;
             }
 
@@ -286,4 +287,9 @@ private function extractConfigurationFromRequest(ServerRequestInterface $request
 
         return $object;
     }
+
+    private function handleFrontendAndBackendPaths(string $frontendPath, UriInterface $targetUri, string $baseBackendPath = ''): string
+    {
+        return rtrim($frontendPath, '/') . ($targetUri->getPath() !== '' ? '/' . ltrim(substr($targetUri->getPath(), strlen($baseBackendPath)), '/') : '');
+    }
 }
diff --git a/Tests/Unit/Utility/UrlUtilityTest.php b/Tests/Unit/Utility/UrlUtilityTest.php
index 73f176e3..8c8d185b 100644
--- a/Tests/Unit/Utility/UrlUtilityTest.php
+++ b/Tests/Unit/Utility/UrlUtilityTest.php
@@ -29,13 +29,12 @@
 class UrlUtilityTest extends UnitTestCase
 {
     use ProphecyTrait;
-
     public function testFrontendUrls(): void
     {
         $headlessMode = $this->createHeadlessMode();
 
         $site = $this->prophesize(Site::class);
-        $site->getBase()->shouldBeCalled(2)->willReturn(new Uri('https://test-backend-api.tld'));
+        $site->getBase()->shouldBeCalled(2)->willReturn(new Uri('https://test-backend-api.tld/'));
         $site->getConfiguration()->shouldBeCalled(3)->willReturn([
             'base' => 'https://www.typo3.org',
             'languages' => [],
@@ -102,7 +101,7 @@ public function testFrontendUrls(): void
 
         $siteFinder = $this->prophesize(SiteFinder::class);
 
-        $site->getBase()->shouldBeCalled(2)->willReturn(new Uri('https://test-backend3-api.tld'));
+        $site->getBase()->shouldBeCalled(2)->willReturn(new Uri('https://test-backend3-api.tld/'));
 
         $urlUtility = new UrlUtility(null, $resolver->reveal(), $siteFinder->reveal(), null, $headlessMode);
         $urlUtility = $urlUtility->withSite($site->reveal());
@@ -115,6 +114,35 @@ public function testFrontendUrls(): void
         self::assertSame('#fragment-123', $urlUtility->getFrontendUrlWithSite('#fragment-123', $site->reveal()));
     }
 
+    public function testFrontendUrlsWithDifferentPaths(): void
+    {
+        $headlessMode = $this->createHeadlessMode();
+
+        $site = $this->prophesize(Site::class);
+        $site->getBase()->shouldBeCalled(1)->willReturn(new Uri('https://test-backend-api.tld/dev-path/'));
+        $site->getConfiguration()->shouldBeCalled(3)->willReturn([
+            'base' => 'https://www.typo3.org',
+            'languages' => [],
+            'baseVariants' => [
+                [
+                    'base' => 'https://test-backend-api.tld/dev-path/',
+                    'condition' => 'applicationContext == "Development"',
+                    'frontendBase' => 'https://test-frontend.tld/frontend',
+                ],
+            ],
+        ]);
+
+        $resolver = $this->prophesize(Resolver::class);
+        $resolver->evaluate(Argument::containingString('Development'))->willReturn(true);
+
+        $siteFinder = $this->prophesize(SiteFinder::class);
+
+        $urlUtility = new UrlUtility(null, $resolver->reveal(), $siteFinder->reveal(), null, $headlessMode);
+        $urlUtility = $urlUtility->withSite($site->reveal());
+
+        self::assertSame('https://test-frontend.tld/frontend/content-page', $urlUtility->getFrontendUrlWithSite('https://test-backend-api.tld/dev-path/content-page', $site->reveal()));
+    }
+
     public function testFrontendUrlsWithBaseProductionAndLocalOverride(): void
     {
         $site = $this->prophesize(Site::class);