diff --git a/README.md b/README.md
index f2c63cf..b9fa114 100644
--- a/README.md
+++ b/README.md
@@ -102,6 +102,24 @@ render for the passed exception class.
 
 **Note** Need to provide the full exception class name (FQCN) to the method, it automatically imports it.
 
+#### addMiddlewarePrependToGroup
+
+Adds middleware to a named group via `prependToGroup` inside the `withMiddleware` closure. 
+Accepts a single class name or string, or an array of them. Skips values that already exist in the target group. 
+Does not affect other groups.
+Supports `InsertPositionEnum::Start` and `InsertPositionEnum::End` to control the insertion position. `End` is used by default.
+
+```php
+new AppBootstrapBuilder(bootstrap_path('app.php'))
+    ->addMiddlewarePrependToGroup('api', [
+        MyMiddleware::class,
+        'throttle:60,1',
+    ])
+    ->addMiddlewarePrependToGroup('web', WebMiddleware::class,, InsertPositionEnum::Start)
+    ->save();
+
+**Note:** Provide the full class name (FQCN) for class-based middleware — the method imports it automatically.
+
 ## Contributing
 
 Thank you for considering contributing to Laravel Builder package! The contribution guide
diff --git a/src/Builders/AppBootstrapBuilder.php b/src/Builders/AppBootstrapBuilder.php
index f3a0316..72b57ab 100644
--- a/src/Builders/AppBootstrapBuilder.php
+++ b/src/Builders/AppBootstrapBuilder.php
@@ -2,7 +2,10 @@
 
 namespace RonasIT\Larabuilder\Builders;
 
+use Illuminate\Support\Arr;
+use RonasIT\Larabuilder\Enums\InsertPositionEnum;
 use RonasIT\Larabuilder\Visitors\AppBootstrapVisitors\AddExceptionsRender;
+use RonasIT\Larabuilder\Visitors\AppBootstrapVisitors\AddMiddlewarePrependToGroup;
 
 class AppBootstrapBuilder extends PHPFileBuilder
 {
@@ -25,4 +28,19 @@ public function addExceptionsRender(string $exceptionClass, string $renderBody,
 
         return $this;
     }
+
+    public function addMiddlewarePrependToGroup(string $group, string|array $middleware, InsertPositionEnum $position = InsertPositionEnum::End): self
+    {
+        $middlewares = Arr::wrap($middleware);
+
+        $this->traverser->addVisitor(new AddMiddlewarePrependToGroup($group, $middlewares, $position));
+
+        $imports = array_filter($middlewares, fn ($middleware) => class_exists($middleware));
+
+        if (!empty($imports)) {
+            $this->addImports($imports);
+        }
+
+        return $this;
+    }
 }
diff --git a/src/Visitors/AppBootstrapVisitors/AbstractAppBootstrapVisitor.php b/src/Visitors/AppBootstrapVisitors/AbstractAppBootstrapVisitor.php
index 3c92660..7243ab7 100644
--- a/src/Visitors/AppBootstrapVisitors/AbstractAppBootstrapVisitor.php
+++ b/src/Visitors/AppBootstrapVisitors/AbstractAppBootstrapVisitor.php
@@ -14,7 +14,7 @@
 
 abstract class AbstractAppBootstrapVisitor extends NodeVisitorAbstract
 {
-    protected const FORBIDDEN_NODES = [
+    protected const array FORBIDDEN_NODES = [
         Class_::class,
         Trait_::class,
         Interface_::class,
diff --git a/src/Visitors/AppBootstrapVisitors/AddMiddlewarePrependToGroup.php b/src/Visitors/AppBootstrapVisitors/AddMiddlewarePrependToGroup.php
new file mode 100644
index 0000000..ea3ca9f
--- /dev/null
+++ b/src/Visitors/AppBootstrapVisitors/AddMiddlewarePrependToGroup.php
@@ -0,0 +1,148 @@
+<?php
+
+namespace RonasIT\Larabuilder\Visitors\AppBootstrapVisitors;
+
+use PhpParser\Node\Arg;
+use PhpParser\Node\ArrayItem;
+use PhpParser\Node\Expr\Array_;
+use PhpParser\Node\Expr\ClassConstFetch;
+use PhpParser\Node\Expr\Closure;
+use PhpParser\Node\Expr\MethodCall;
+use PhpParser\Node\Expr\Variable;
+use PhpParser\Node\Identifier;
+use PhpParser\Node\Name;
+use PhpParser\Node\Scalar\String_;
+use PhpParser\Node\Stmt\Expression;
+use PhpParser\Node\Stmt\Nop;
+use RonasIT\Larabuilder\Enums\InsertPositionEnum;
+
+class AddMiddlewarePrependToGroup extends AbstractAppBootstrapVisitor
+{
+    public function __construct(
+        protected string $group,
+        protected array $middlewares,
+        protected InsertPositionEnum $position,
+    ) {
+        parent::__construct(
+            parentMethod: 'withMiddleware',
+            targetMethod: 'prependToGroup',
+        );
+    }
+
+    protected function insertNode(MethodCall $node): MethodCall
+    {
+        /** @var Closure $closure */
+        $closure = $node->args[0]->value;
+
+        $this->removeNopPlaceholder($closure);
+
+        $statementIndex = $this->findMiddlewareGroupIndex($closure->stmts);
+
+        if (is_null($statementIndex)) {
+            $closure->stmts[] = $this->buildPrependToGroupCall();
+        } else {
+            $this->updateMiddlewareGroup($closure, $statementIndex);
+        }
+
+        return $node;
+    }
+
+    protected function removeNopPlaceholder(Closure $closure): void
+    {
+        if (!empty($closure->stmts) && ($closure->stmts[0] ?? null) instanceof Nop) {
+            array_shift($closure->stmts);
+        }
+    }
+
+    protected function findMiddlewareGroupIndex(array $stmts): ?int
+    {
+        return array_find_key($stmts, function (Expression $stmt) {
+            return !empty($stmt->expr->name)
+                && $stmt->expr->name->toString() === $this->targetMethod
+                && $stmt->expr->args[0]->value->value === $this->group;
+        });
+    }
+
+    protected function updateMiddlewareGroup(Closure $closure, int $groupIndex): void
+    {
+        $originalMiddlewares = $closure->stmts[$groupIndex]->expr->args[1]->value->value
+            ?? $closure->stmts[$groupIndex]->expr->args[1]->value->class->name
+            ?? $closure->stmts[$groupIndex]->expr->args[1]->value->items;
+
+        $originalMiddlewares = is_array($originalMiddlewares)
+            ? $originalMiddlewares
+            : [new ArrayItem($closure->stmts[$groupIndex]->expr->args[1]->value)];
+
+        $mergedMiddlewares = $this->mergeMiddlewares($originalMiddlewares);
+
+        $closure->stmts[$groupIndex]->expr->args[1] = $this->buildMiddlewareArg($mergedMiddlewares);
+    }
+
+    protected function mergeMiddlewares(array $originalMiddlewareList): array
+    {
+        $filteredNewList = [];
+
+        foreach ($this->middlewares as $middleware) {
+            $sameMiddlewareKey = array_find_key(
+                $originalMiddlewareList,
+                fn ($originalMiddleware) => $this->isSameMiddleware($middleware, $originalMiddleware),
+            );
+
+            if (is_null($sameMiddlewareKey)) {
+                $filteredNewList[] = $this->makeArrayItem($middleware);
+            }
+        }
+
+        return match ($this->position) {
+            InsertPositionEnum::Start => [...$filteredNewList, ...$originalMiddlewareList],
+            InsertPositionEnum::End => [...$originalMiddlewareList, ...$filteredNewList],
+        };
+    }
+
+    protected function isSameMiddleware(string $newMiddleware, ArrayItem $originalMiddleware): bool
+    {
+        if ($originalMiddleware->value instanceof ClassConstFetch) {
+            $originalName = $originalMiddleware->value->class->name;
+
+            return $originalName === $newMiddleware
+                || $originalName === class_basename($newMiddleware);
+        }
+
+        return $originalMiddleware->value->value === $newMiddleware;
+    }
+
+    protected function buildPrependToGroupCall(): Expression
+    {
+        $middlewareList = $this->getMiddlewareList();
+
+        $methodCall = new MethodCall(new Variable('middleware'), new Identifier($this->targetMethod), [
+            new Arg(new String_($this->group)),
+            $this->buildMiddlewareArg($middlewareList),
+        ]);
+
+        return new Expression($methodCall);
+    }
+
+    protected function buildMiddlewareArg(array $middlewares): Arg
+    {
+        return new Arg(new Array_($middlewares));
+    }
+
+    protected function getMiddlewareList(): array
+    {
+        return array_map(fn ($middleware) => $this->makeArrayItem($middleware), $this->middlewares);
+    }
+
+    protected function makeArrayItem(string $middleware): ArrayItem
+    {
+        if (class_exists($middleware)) {
+            $basename = class_basename($middleware);
+
+            $value = new ClassConstFetch(new Name($basename), 'class');
+        } else {
+            $value = new String_($middleware);
+        }
+
+        return new ArrayItem($value);
+    }
+}
diff --git a/tests/AppBootstrapBuilderTest.php b/tests/AppBootstrapBuilderTest.php
index 6945e47..8c02c15 100644
--- a/tests/AppBootstrapBuilderTest.php
+++ b/tests/AppBootstrapBuilderTest.php
@@ -2,11 +2,14 @@
 
 namespace RonasIT\Larabuilder\Tests;
 
+use Illuminate\Auth\Middleware\Authenticate;
 use PHPUnit\Framework\Attributes\DataProvider;
 use PHPUnit\Framework\ExpectationFailedException;
 use RonasIT\Larabuilder\Builders\AppBootstrapBuilder;
+use RonasIT\Larabuilder\Enums\InsertPositionEnum;
 use RonasIT\Larabuilder\Exceptions\InvalidBootstrapAppFileException;
 use RonasIT\Larabuilder\Exceptions\InvalidPHPCodeException;
+use RonasIT\Larabuilder\Tests\Support\Classes\FakeClass;
 use RonasIT\Larabuilder\Tests\Support\Traits\PHPFileBuilderTestMockTrait;
 use Symfony\Component\HttpKernel\Exception\HttpException;
 
@@ -137,4 +140,78 @@ public function testInvalidBootstrapAppFileException(string $fixture, string $ty
             )
             ->save();
     }
+
+    public function testAddMiddlewarePrependToGroup()
+    {
+        $file = $this->generateOriginalStructurePath('bootstrap_empty.php');
+
+        $this->mockNativeFunction(
+            'RonasIT\Larabuilder\Builders',
+            $this->callFilePutContent($file, 'bootstrap_with_prepend_group.php'),
+        );
+
+        new AppBootstrapBuilder($file)
+            ->addMiddlewarePrependToGroup(
+                group: 'api',
+                middleware: FakeClass::class,
+            )
+            ->addMiddlewarePrependToGroup(
+                group: 'api',
+                middleware: 'throttle:60,10',
+                position: InsertPositionEnum::Start,
+            )
+            ->addMiddlewarePrependToGroup(
+                group: 'web',
+                middleware: [
+                    'throttle:10,10',
+                    FakeClass::class,
+                ],
+            )
+            ->save();
+    }
+
+    public function testAddMiddlewarePrependToGroupExistsMiddlewares()
+    {
+        $file = $this->generateOriginalStructurePath('bootstrap_with_prepend_group.php');
+
+        $this->mockNativeFunction(
+            'RonasIT\Larabuilder\Builders',
+            $this->callFilePutContent($file, 'bootstrap_without_changed_prepend_group.php'),
+        );
+
+        new AppBootstrapBuilder($file)
+            ->addMiddlewarePrependToGroup('api', [
+                'throttle:60,10',
+                Authenticate::class,
+            ])
+            ->save();
+    }
+
+    public static function provideMiddlewareAsString(): array
+    {
+        return [
+            [
+                'original' => 'bootstrap_with_prepend_group_as_string.php',
+                'result' => 'bootstrap_with_prepend_group_as_string.php',
+            ],
+            [
+                'original' => 'bootstrap_with_prepend_group_as_string_set_class.php',
+                'result' => 'bootstrap_with_prepend_group_as_string_set_class.php',
+            ],
+        ];
+    }
+
+    #[DataProvider('provideMiddlewareAsString')]
+    public function testAddMiddlewarePrependToGroupMiddlewareAsString(string $original, string $result): void
+    {
+        $file = $this->generateOriginalStructurePath($original);
+
+        $this->mockNativeFunction('RonasIT\Larabuilder\Builders', $this->callFilePutContent($file, $result));
+
+        new AppBootstrapBuilder($file)
+            ->addMiddlewarePrependToGroup('api', [
+                'some_middleware',
+            ])
+            ->save();
+    }
 }
diff --git a/tests/Support/Classes/FakeClass.php b/tests/Support/Classes/FakeClass.php
new file mode 100644
index 0000000..e11cb28
--- /dev/null
+++ b/tests/Support/Classes/FakeClass.php
@@ -0,0 +1,7 @@
+<?php
+
+namespace RonasIT\Larabuilder\Tests\Support\Classes;
+
+class FakeClass
+{
+}
diff --git a/tests/Support/OriginStructures/bootstrap_with_prepend_group.php b/tests/Support/OriginStructures/bootstrap_with_prepend_group.php
new file mode 100644
index 0000000..0052a0e
--- /dev/null
+++ b/tests/Support/OriginStructures/bootstrap_with_prepend_group.php
@@ -0,0 +1,19 @@
+<?php
+
+use Illuminate\Foundation\Application;
+use Illuminate\Foundation\Configuration\Exceptions;
+use Illuminate\Foundation\Configuration\Middleware;
+use Illuminate\Auth\Middleware\Authenticate;
+
+return Application::configure(basePath: dirname(__DIR__))
+    ->withRouting(
+        web: __DIR__.'/../routes/web.php',
+        commands: __DIR__.'/../routes/console.php',
+        health: '/up',
+    )
+    ->withMiddleware(function (Middleware $middleware): void {
+        $middleware->prependToGroup('api', ['throttle:60,10', Authenticate::class]);
+    })
+    ->withExceptions(function (Exceptions $exceptions): void {
+        //
+    })->create();
diff --git a/tests/Support/OriginStructures/bootstrap_with_prepend_group_as_string.php b/tests/Support/OriginStructures/bootstrap_with_prepend_group_as_string.php
new file mode 100644
index 0000000..b09e30a
--- /dev/null
+++ b/tests/Support/OriginStructures/bootstrap_with_prepend_group_as_string.php
@@ -0,0 +1,18 @@
+<?php
+
+use Illuminate\Foundation\Application;
+use Illuminate\Foundation\Configuration\Exceptions;
+use Illuminate\Foundation\Configuration\Middleware;
+
+return Application::configure(basePath: dirname(__DIR__))
+    ->withRouting(
+        web: __DIR__.'/../routes/web.php',
+        commands: __DIR__.'/../routes/console.php',
+        health: '/up',
+    )
+    ->withMiddleware(function (Middleware $middleware): void {
+        $middleware->prependToGroup('api', 'throttle:60,10');
+    })
+    ->withExceptions(function (Exceptions $exceptions): void {
+        //
+    })->create();
diff --git a/tests/Support/OriginStructures/bootstrap_with_prepend_group_as_string_set_class.php b/tests/Support/OriginStructures/bootstrap_with_prepend_group_as_string_set_class.php
new file mode 100644
index 0000000..e334479
--- /dev/null
+++ b/tests/Support/OriginStructures/bootstrap_with_prepend_group_as_string_set_class.php
@@ -0,0 +1,18 @@
+<?php
+
+use Illuminate\Foundation\Application;
+use Illuminate\Foundation\Configuration\Exceptions;
+use Illuminate\Foundation\Configuration\Middleware;
+
+return Application::configure(basePath: dirname(__DIR__))
+    ->withRouting(
+        web: __DIR__.'/../routes/web.php',
+        commands: __DIR__.'/../routes/console.php',
+        health: '/up',
+    )
+    ->withMiddleware(function (Middleware $middleware): void {
+        $middleware->prependToGroup('api', \Illuminate\Auth\Middleware\Authenticate::class);
+    })
+    ->withExceptions(function (Exceptions $exceptions): void {
+        //
+    })->create();
diff --git a/tests/fixtures/AppBootstrapBuilderTest/bootstrap_with_prepend_group.php b/tests/fixtures/AppBootstrapBuilderTest/bootstrap_with_prepend_group.php
new file mode 100644
index 0000000..9dd5260
--- /dev/null
+++ b/tests/fixtures/AppBootstrapBuilderTest/bootstrap_with_prepend_group.php
@@ -0,0 +1,20 @@
+<?php
+
+use Illuminate\Foundation\Application;
+use Illuminate\Foundation\Configuration\Exceptions;
+use Illuminate\Foundation\Configuration\Middleware;
+use RonasIT\Larabuilder\Tests\Support\Classes\FakeClass;
+
+return Application::configure(basePath: dirname(__DIR__))
+    ->withRouting(
+        web: __DIR__.'/../routes/web.php',
+        commands: __DIR__.'/../routes/console.php',
+        health: '/up',
+    )
+    ->withMiddleware(function (Middleware $middleware): void {
+        $middleware->prependToGroup('api', ['throttle:60,10', FakeClass::class]);
+        $middleware->prependToGroup('web', ['throttle:10,10', FakeClass::class]);
+    })
+    ->withExceptions(function (Exceptions $exceptions): void {
+        //
+    })->create();
diff --git a/tests/fixtures/AppBootstrapBuilderTest/bootstrap_with_prepend_group_as_string.php b/tests/fixtures/AppBootstrapBuilderTest/bootstrap_with_prepend_group_as_string.php
new file mode 100644
index 0000000..bd7306b
--- /dev/null
+++ b/tests/fixtures/AppBootstrapBuilderTest/bootstrap_with_prepend_group_as_string.php
@@ -0,0 +1,18 @@
+<?php
+
+use Illuminate\Foundation\Application;
+use Illuminate\Foundation\Configuration\Exceptions;
+use Illuminate\Foundation\Configuration\Middleware;
+
+return Application::configure(basePath: dirname(__DIR__))
+    ->withRouting(
+        web: __DIR__.'/../routes/web.php',
+        commands: __DIR__.'/../routes/console.php',
+        health: '/up',
+    )
+    ->withMiddleware(function (Middleware $middleware): void {
+        $middleware->prependToGroup('api', ['throttle:60,10', 'some_middleware']);
+    })
+    ->withExceptions(function (Exceptions $exceptions): void {
+        //
+    })->create();
diff --git a/tests/fixtures/AppBootstrapBuilderTest/bootstrap_with_prepend_group_as_string_set_class.php b/tests/fixtures/AppBootstrapBuilderTest/bootstrap_with_prepend_group_as_string_set_class.php
new file mode 100644
index 0000000..bed591c
--- /dev/null
+++ b/tests/fixtures/AppBootstrapBuilderTest/bootstrap_with_prepend_group_as_string_set_class.php
@@ -0,0 +1,18 @@
+<?php
+
+use Illuminate\Foundation\Application;
+use Illuminate\Foundation\Configuration\Exceptions;
+use Illuminate\Foundation\Configuration\Middleware;
+
+return Application::configure(basePath: dirname(__DIR__))
+    ->withRouting(
+        web: __DIR__.'/../routes/web.php',
+        commands: __DIR__.'/../routes/console.php',
+        health: '/up',
+    )
+    ->withMiddleware(function (Middleware $middleware): void {
+        $middleware->prependToGroup('api', [\Illuminate\Auth\Middleware\Authenticate::class, 'some_middleware']);
+    })
+    ->withExceptions(function (Exceptions $exceptions): void {
+        //
+    })->create();
diff --git a/tests/fixtures/AppBootstrapBuilderTest/bootstrap_without_changed_prepend_group.php b/tests/fixtures/AppBootstrapBuilderTest/bootstrap_without_changed_prepend_group.php
new file mode 100644
index 0000000..0052a0e
--- /dev/null
+++ b/tests/fixtures/AppBootstrapBuilderTest/bootstrap_without_changed_prepend_group.php
@@ -0,0 +1,19 @@
+<?php
+
+use Illuminate\Foundation\Application;
+use Illuminate\Foundation\Configuration\Exceptions;
+use Illuminate\Foundation\Configuration\Middleware;
+use Illuminate\Auth\Middleware\Authenticate;
+
+return Application::configure(basePath: dirname(__DIR__))
+    ->withRouting(
+        web: __DIR__.'/../routes/web.php',
+        commands: __DIR__.'/../routes/console.php',
+        health: '/up',
+    )
+    ->withMiddleware(function (Middleware $middleware): void {
+        $middleware->prependToGroup('api', ['throttle:60,10', Authenticate::class]);
+    })
+    ->withExceptions(function (Exceptions $exceptions): void {
+        //
+    })->create();