diff --git a/packages/BetterPhpDocParser/PhpDocParser/DoctrineAnnotationDecorator.php b/packages/BetterPhpDocParser/PhpDocParser/DoctrineAnnotationDecorator.php
index e5c252105fe..542864bc2bc 100644
--- a/packages/BetterPhpDocParser/PhpDocParser/DoctrineAnnotationDecorator.php
+++ b/packages/BetterPhpDocParser/PhpDocParser/DoctrineAnnotationDecorator.php
@@ -157,15 +157,18 @@ private function transformGenericTagValueNodesToDoctrineAnnotationTagValueNodes(
         foreach ($phpDocNode->children as $key => $phpDocChildNode) {
             // the @\FQN use case
             if ($phpDocChildNode instanceof PhpDocTextNode) {
-                $spacelessPhpDocTagNode = $this->resolveFqnAnnotationSpacelessPhpDocTagNode(
+                $spacelessPhpDocTagNodes = $this->resolveFqnAnnotationSpacelessPhpDocTagNode(
                     $phpDocChildNode,
                     $currentPhpNode
                 );
-                if (! $spacelessPhpDocTagNode instanceof SpacelessPhpDocTagNode) {
+
+                if ($spacelessPhpDocTagNodes === []) {
                     continue;
                 }
 
-                $phpDocNode->children[$key] = $spacelessPhpDocTagNode;
+                unset($phpDocNode->children[$key]);
+                array_splice($phpDocNode->children, $key, 0, $spacelessPhpDocTagNodes);
+
                 continue;
             }
 
@@ -304,28 +307,36 @@ private function combineStartAndEnd(
         return new StartAndEnd($currentStartAndEnd->getStart(), $nextStartAndEnd->getEnd());
     }
 
+    /**
+     * @return SpacelessPhpDocTagNode[]
+     */
     private function resolveFqnAnnotationSpacelessPhpDocTagNode(
         PhpDocTextNode $phpDocTextNode,
         Node $currentPhpNode
-    ): ?SpacelessPhpDocTagNode {
-        $match = Strings::match($phpDocTextNode->text, self::LONG_ANNOTATION_REGEX);
-        $fullyQualifiedAnnotationClass = $match['class_name'] ?? null;
+    ): array {
+        $matches = Strings::matchAll($phpDocTextNode->text, self::LONG_ANNOTATION_REGEX);
+        $spacelessPhpDocTagNodes = [];
+        foreach ($matches as $match) {
+            $fullyQualifiedAnnotationClass = $match['class_name'] ?? null;
 
-        if ($fullyQualifiedAnnotationClass === null) {
-            return null;
-        }
+            if ($fullyQualifiedAnnotationClass === null) {
+                continue;
+            }
 
-        $annotationContent = $match['annotation_content'] ?? null;
-        $tagName = '@\\' . $fullyQualifiedAnnotationClass;
+            $annotationContent = $match['annotation_content'] ?? null;
+            $tagName = '@\\' . $fullyQualifiedAnnotationClass;
 
-        $formerStartEnd = $phpDocTextNode->getAttribute(PhpDocAttributeKey::START_AND_END);
+            $formerStartEnd = $phpDocTextNode->getAttribute(PhpDocAttributeKey::START_AND_END);
 
-        return $this->createDoctrineSpacelessPhpDocTagNode(
-            $annotationContent,
-            $tagName,
-            $fullyQualifiedAnnotationClass,
-            $formerStartEnd,
-            $currentPhpNode
-        );
+            $spacelessPhpDocTagNodes[] = $this->createDoctrineSpacelessPhpDocTagNode(
+                $annotationContent,
+                $tagName,
+                $fullyQualifiedAnnotationClass,
+                $formerStartEnd,
+                $currentPhpNode
+            );
+        }
+
+        return $spacelessPhpDocTagNodes;
     }
 }
diff --git a/packages/BetterPhpDocParser/Printer/PhpDocInfoPrinter.php b/packages/BetterPhpDocParser/Printer/PhpDocInfoPrinter.php
index 6a60eb3462e..88ef57acd07 100644
--- a/packages/BetterPhpDocParser/Printer/PhpDocInfoPrinter.php
+++ b/packages/BetterPhpDocParser/Printer/PhpDocInfoPrinter.php
@@ -257,7 +257,7 @@ private function printEnd(string $output): string
         }
 
         if ($lastTokenPosition === 0) {
-            $lastTokenPosition = 1;
+            return $output . "\n */";
         }
 
         return $this->addTokensFromTo($output, $lastTokenPosition, $this->tokenCount, true);
diff --git a/tests/Issues/AutoImport/Fixture/DocBlock/skip_two_routes_with_prev_doc.php.inc b/tests/Issues/AutoImport/Fixture/DocBlock/skip_two_routes_with_prev_doc.php.inc
new file mode 100644
index 00000000000..67f6ff55f39
--- /dev/null
+++ b/tests/Issues/AutoImport/Fixture/DocBlock/skip_two_routes_with_prev_doc.php.inc
@@ -0,0 +1,16 @@
+<?php
+
+namespace Rector\Core\Tests\Issues\AutoImport\Fixture\DocBlock;
+
+class TwoRoutesWithPrevDoc
+{
+    /**
+     * @return Response
+     * @\Symfony\Component\Routing\Annotation\Route("/first", methods={"GET"})
+     * @\Symfony\Component\Routing\Annotation\Route("/second", methods={"GET"})
+     */
+    public function some(): Response
+    {
+        return new Response();
+    }
+}
diff --git a/tests/Issues/AutoImport/Fixture/DocBlock/two_routes.php.inc b/tests/Issues/AutoImport/Fixture/DocBlock/two_routes.php.inc
new file mode 100644
index 00000000000..87630ee1566
--- /dev/null
+++ b/tests/Issues/AutoImport/Fixture/DocBlock/two_routes.php.inc
@@ -0,0 +1,36 @@
+<?php
+
+namespace Rector\Core\Tests\Issues\AutoImport\Fixture\DocBlock;
+
+class TwoRoutes
+{
+    /**
+     * @\Symfony\Component\Routing\Annotation\Route("/first", methods={"GET"})
+     * @\Symfony\Component\Routing\Annotation\Route("/second", methods={"GET"})
+     */
+    public function some(): Response
+    {
+        return new Response();
+    }
+}
+
+?>
+-----
+<?php
+
+namespace Rector\Core\Tests\Issues\AutoImport\Fixture\DocBlock;
+
+use Symfony\Component\Routing\Annotation\Route;
+class TwoRoutes
+{
+    /**
+     * @Route("/first", methods={"GET"})
+     * @Route("/second", methods={"GET"})
+     */
+    public function some(): Response
+    {
+        return new Response();
+    }
+}
+
+?>
diff --git a/tests/Issues/AutoImport/Fixture/DocBlock/two_routes_with_next_doc.php.inc b/tests/Issues/AutoImport/Fixture/DocBlock/two_routes_with_next_doc.php.inc
new file mode 100644
index 00000000000..5c9c316ee7a
--- /dev/null
+++ b/tests/Issues/AutoImport/Fixture/DocBlock/two_routes_with_next_doc.php.inc
@@ -0,0 +1,38 @@
+<?php
+
+namespace Rector\Core\Tests\Issues\AutoImport\Fixture\DocBlock;
+
+class TwoRoutesWithNextDoc
+{
+    /**
+     * @\Symfony\Component\Routing\Annotation\Route("/first", methods={"GET"})
+     * @\Symfony\Component\Routing\Annotation\Route("/second", methods={"GET"})
+     * @return Response
+     */
+    public function some(): Response
+    {
+        return new Response();
+    }
+}
+
+?>
+-----
+<?php
+
+namespace Rector\Core\Tests\Issues\AutoImport\Fixture\DocBlock;
+
+use Symfony\Component\Routing\Annotation\Route;
+class TwoRoutesWithNextDoc
+{
+    /**
+     * @Route("/first", methods={"GET"})
+     * @Route("/second", methods={"GET"})
+     * @return Response
+     */
+    public function some(): Response
+    {
+        return new Response();
+    }
+}
+
+?>
diff --git a/tests/Issues/AutoImport/Fixture/DocBlock/two_routes_with_next_doc_other_routes.php.inc b/tests/Issues/AutoImport/Fixture/DocBlock/two_routes_with_next_doc_other_routes.php.inc
new file mode 100644
index 00000000000..5a29821370e
--- /dev/null
+++ b/tests/Issues/AutoImport/Fixture/DocBlock/two_routes_with_next_doc_other_routes.php.inc
@@ -0,0 +1,40 @@
+<?php
+
+namespace Rector\Core\Tests\Issues\AutoImport\Fixture\DocBlock;
+
+class TwoRoutesWithNextDoc2
+{
+    /**
+     * @\Symfony\Component\Routing\Annotation\Route("/first", methods={"GET"})
+     * @\Symfony\Component\Routing\Annotation\Route("/second", methods={"GET"})
+     * @return Response
+     * @\Symfony\Component\Routing\Annotation\Route("/third", methods={"GET"})
+     */
+    public function some(): Response
+    {
+        return new Response();
+    }
+}
+
+?>
+-----
+<?php
+
+namespace Rector\Core\Tests\Issues\AutoImport\Fixture\DocBlock;
+
+use Symfony\Component\Routing\Annotation\Route;
+class TwoRoutesWithNextDoc2
+{
+    /**
+     * @Route("/first", methods={"GET"})
+     * @Route("/second", methods={"GET"})
+     * @return Response
+     * @\Symfony\Component\Routing\Annotation\Route("/third", methods={"GET"})
+     */
+    public function some(): Response
+    {
+        return new Response();
+    }
+}
+
+?>
\ No newline at end of file