diff --git a/README.md b/README.md
index d7cd071..489dab2 100644
--- a/README.md
+++ b/README.md
@@ -223,6 +223,116 @@ $openapi = new OpenApi([
 $json = \cebe\openapi\Writer::writeToJson($openapi);
 ```
 
+Write empty Security Requirement Object (`{}`):
+
+```php
+$openapi = new OpenApi([
+    ...
+    'security' => new SecurityRequirements([
+        []
+    ]
+    ...
+]);
+```
+
+```yaml
+...
+security:
+  - {}
+...
+```
+
+Write security for multiple authentication:
+
+```php
+$openapi = new OpenApi([
+    ...
+    'components' => new Components([
+        'securitySchemes' => [
+            'BearerAuth' => new SecurityScheme([
+                'type' => 'http',
+                'scheme' => 'bearer',
+            ]),
+            'BasicAuth' => new SecurityScheme([
+                'type' => 'http',
+                'scheme' => 'basic',
+            ]),
+            'ApiKeyAuth' => new SecurityScheme([
+                'type' => 'apiKey',
+                'name' => 'X-API-Key',
+                'in' => 'header'
+            ])
+        ],
+    ]),
+    'security' => new SecurityRequirements([
+        [
+            'BearerAuth' => new SecurityRequirement([]),
+            'BasicAuth' => new SecurityRequirement([])
+        ],
+        [
+            'ApiKeyAuth' => new SecurityRequirement([])
+        ]
+    ]),
+    ...
+]);
+```
+
+```yaml
+security:
+  -
+    BearerAuth: []
+    BasicAuth: []
+  -
+    ApiKeyAuth: []
+
+```
+
+Write single authentication (note that both below case will yield same output):
+
+```php
+$openapi = new OpenApi([
+    ...
+    'components' => new Components([
+        'securitySchemes' => [
+            'BearerAuth' => new SecurityScheme([
+                'type' => 'http',
+                'scheme' => 'bearer',
+            ])
+        ],
+    ]),
+    'security' => new SecurityRequirements([
+        'BearerAuth' => new SecurityRequirement([])
+    ]),
+    ...
+]);
+```
+
+```php
+$openapi = new OpenApi([
+    ...
+    'components' => new Components([
+        'securitySchemes' => [
+            'BearerAuth' => new SecurityScheme([
+                'type' => 'http',
+                'scheme' => 'bearer',
+            ])
+        ],
+    ]),
+    'security' => new SecurityRequirements([
+        [
+            'BearerAuth' => new SecurityRequirement([])
+        ]
+    ]),
+    ...
+]);
+```
+
+```yaml
+security:
+  -
+    BearerAuth: []
+```
+
 ### Reading API Description Files and Resolving References
 
 In the above we have passed the raw JSON or YAML data to the Reader. In order to be able to resolve
diff --git a/src/spec/SecurityRequirements.php b/src/spec/SecurityRequirements.php
index cbda1ba..58a5d3b 100644
--- a/src/spec/SecurityRequirements.php
+++ b/src/spec/SecurityRequirements.php
@@ -24,12 +24,20 @@ public function __construct(array $data)
         parent::__construct($data);
 
         foreach ($data as $index => $value) {
-            if (is_numeric($index)) { // read
-                $this->_securityRequirements[array_keys($value)[0]] = new SecurityRequirement(array_values($value)[0]);
-            } else { // write
-                $this->_securityRequirements[$index] = $value;
+            if (is_numeric($index) && $value === []) { # empty Security Requirement Object (`{}`) = anonymous access
+                $this->_securityRequirements[$index] = [];
+                continue;
+            }
+
+            if (is_string($index)) {
+                $this->_securityRequirements[] = [$index => $value instanceof SecurityRequirement ? $value : new SecurityRequirement($value)];
+            } elseif (is_numeric($index)) {
+                foreach ($value as $innerIndex => $subValue) {
+                    $this->_securityRequirements[$index][$innerIndex] = $subValue instanceof SecurityRequirement ? $subValue : new SecurityRequirement($subValue);
+                }
             }
         }
+
         if ($data === []) {
             $this->_securityRequirements = [];
         }
@@ -59,20 +67,50 @@ protected function performValidation()
     public function getSerializableData()
     {
         $data = [];
-        foreach ($this->_securityRequirements ?? [] as $name => $securityRequirement) {
-            /** @var SecurityRequirement $securityRequirement */
-            $data[] = [$name => $securityRequirement->getSerializableData()];
+
+        foreach ($this->_securityRequirements ?? [] as $outerIndex => $content) {
+            if (is_string($outerIndex)) {
+                $data[] = [$outerIndex => $content->getSerializableData()];
+            } elseif (is_numeric($outerIndex)) {
+                if ($content === []) {
+                    $data[$outerIndex] = (object)$content;
+                    continue;
+                }
+                $innerResult = [];
+                foreach ($content as $innerIndex => $innerContent) {
+                    $result = is_object($innerContent) && method_exists($innerContent, 'getSerializableData') ? $innerContent->getSerializableData() : $innerContent;
+                    $innerResult[$innerIndex] = $result;
+                }
+                $data[$outerIndex] = (object)$innerResult;
+            }
         }
         return $data;
     }
 
     public function getRequirement(string $name)
     {
-        return $this->_securityRequirements[$name] ?? null;
+        return static::searchKey($this->_securityRequirements, $name);
     }
 
     public function getRequirements()
     {
         return $this->_securityRequirements;
     }
+
+    private static function searchKey(array $array, string $searchKey)
+    {
+        foreach ($array as $key => $value) {
+            if ($key === $searchKey) {
+                return $value;
+            }
+            if (is_array($value)) {
+                $mt = __METHOD__;
+                $result = $mt($value, $searchKey);
+                if ($result !== null) {
+                    return $result; // key found in deeply nested/associative array
+                }
+            }
+        }
+        return null; // key not found
+    }
 }
diff --git a/tests/WriterTest.php b/tests/WriterTest.php
index 355a744..d6112d0 100644
--- a/tests/WriterTest.php
+++ b/tests/WriterTest.php
@@ -8,6 +8,7 @@
 use cebe\openapi\spec\SecurityRequirement;
 use cebe\openapi\spec\SecurityRequirements;
 use cebe\openapi\spec\SecurityScheme;
+use cebe\openapi\Writer;
 
 class WriterTest extends \PHPUnit\Framework\TestCase
 {
@@ -27,7 +28,7 @@ public function testWriteJson()
     {
         $openapi = $this->createOpenAPI();
 
-        $json = \cebe\openapi\Writer::writeToJson($openapi);
+        $json = Writer::writeToJson($openapi);
 
         $this->assertEquals(preg_replace('~\R~', "\n", <<<JSON
 {
@@ -52,7 +53,7 @@ public function testWriteJsonMofify()
             'description' => 'something'
         ]);
 
-        $json = \cebe\openapi\Writer::writeToJson($openapi);
+        $json = Writer::writeToJson($openapi);
 
         $this->assertEquals(preg_replace('~\R~', "\n", <<<JSON
 {
@@ -77,7 +78,7 @@ public function testWriteYaml()
     {
         $openapi = $this->createOpenAPI();
 
-        $yaml = \cebe\openapi\Writer::writeToYaml($openapi);
+        $yaml = Writer::writeToYaml($openapi);
 
 
         $this->assertEquals(preg_replace('~\R~', "\n", <<<YAML
@@ -99,7 +100,7 @@ public function testWriteEmptySecurityJson()
             'security' => [],
         ]);
 
-        $json = \cebe\openapi\Writer::writeToJson($openapi);
+        $json = Writer::writeToJson($openapi);
 
         $this->assertEquals(preg_replace('~\R~', "\n", <<<JSON
 {
@@ -124,7 +125,7 @@ public function testWriteEmptySecurityYaml()
             'security' => [],
         ]);
 
-        $yaml = \cebe\openapi\Writer::writeToYaml($openapi);
+        $yaml = Writer::writeToYaml($openapi);
 
 
         $this->assertEquals(preg_replace('~\R~', "\n", <<<YAML
@@ -149,7 +150,7 @@ public function testWriteEmptySecurityPartJson()
             ]),
         ]);
 
-        $json = \cebe\openapi\Writer::writeToJson($openapi);
+        $json = Writer::writeToJson($openapi);
 
         $this->assertEquals(preg_replace('~\R~', "\n", <<<JSON
 {
@@ -180,7 +181,7 @@ public function testWriteEmptySecurityPartYaml()
             ]),
         ]);
 
-        $yaml = \cebe\openapi\Writer::writeToYaml($openapi);
+        $yaml = Writer::writeToYaml($openapi);
 
 
         $this->assertEquals(preg_replace('~\R~', "\n", <<<YAML
@@ -225,7 +226,7 @@ public function testSecurityAtPathOperationLevel()
             ]
         ]);
 
-        $yaml = \cebe\openapi\Writer::writeToYaml($openapi);
+        $yaml = Writer::writeToYaml($openapi);
 
 
         $this->assertEquals(preg_replace('~\R~', "\n", <<<YAML
@@ -272,11 +273,30 @@ public function testSecurityAtGlobalLevel()
             ]),
             'paths' => [],
         ]);
+        $yaml = Writer::writeToYaml($openapi);
 
-        $yaml = \cebe\openapi\Writer::writeToYaml($openapi);
+        // case 2
+        $openapi2 = $this->createOpenAPI([
+            'components' => new Components([
+                'securitySchemes' => [
+                    'BearerAuth' => new SecurityScheme([
+                        'type' => 'http',
+                        'scheme' => 'bearer',
+                        'bearerFormat' => 'AuthToken and JWT Format' # optional, arbitrary value for documentation purposes
+                    ])
+                ],
+            ]),
+            'security' => new SecurityRequirements([
+                [
+                    'BearerAuth' => new SecurityRequirement([])
+                ]
+            ]),
+            'paths' => [],
+        ]);
+        $yaml2 = Writer::writeToYaml($openapi2);
 
 
-        $this->assertEquals(preg_replace('~\R~', "\n", <<<YAML
+        $expected = <<<YAML
 openapi: 3.0.0
 info:
   title: 'Test API'
@@ -292,9 +312,9 @@ public function testSecurityAtGlobalLevel()
   -
     BearerAuth: []
 
-YAML
-        ),
-            $yaml
-        );
+YAML;
+
+        $this->assertEquals(preg_replace('~\R~', "\n", $expected), $yaml);
+        $this->assertEquals(preg_replace('~\R~', "\n", $expected), $yaml2);
     }
 }
diff --git a/tests/data/issue/238/spec.yml b/tests/data/issue/238/spec.yml
new file mode 100644
index 0000000..df9c183
--- /dev/null
+++ b/tests/data/issue/238/spec.yml
@@ -0,0 +1,28 @@
+openapi: 3.0.0
+info:
+  title: Secured API
+  version: 1.0.0
+paths:
+  /global-secured:
+    get:
+      responses:
+        '200':
+          description: OK
+  /path-secured:
+    get:
+      security:
+        - {}
+      responses:
+        '200':
+          description: OK
+components:
+  securitySchemes:
+    ApiKeyAuth:
+      type: apiKey
+      in: header
+      name: X-API-Key
+    BearerAuth:
+      type: http
+      scheme: bearer
+security:
+  - ApiKeyAuth: []
diff --git a/tests/data/issue/242/multiple_auth.yml b/tests/data/issue/242/multiple_auth.yml
new file mode 100644
index 0000000..904663f
--- /dev/null
+++ b/tests/data/issue/242/multiple_auth.yml
@@ -0,0 +1,39 @@
+openapi: 3.0.0
+info:
+  title: Multiple auth
+  version: 1.0.0
+paths: {}
+components:
+  securitySchemes:
+    BasicAuth:
+      type: http
+      scheme: basic
+
+    BearerAuth:
+      type: http
+      scheme: bearer
+
+    ApiKeyAuth:
+      type: apiKey
+      in: header
+      name: X-API-Key
+
+    OpenID:
+      type: openIdConnect
+      openIdConnectUrl: https://example.com/.well-known/openid-configuration
+
+    OAuth2:
+      type: oauth2
+      flows:
+        authorizationCode:
+          authorizationUrl: https://example.com/oauth/authorize
+          tokenUrl: https://example.com/oauth/token
+          scopes:
+            read: Grants read access
+            write: Grants write access
+            admin: Grants access to admin operations
+security:
+  - BasicAuth: []
+    BearerAuth: []
+  - ApiKeyAuth: []
+    OAuth2: [read]
\ No newline at end of file
diff --git a/tests/data/issue/242/spec.json b/tests/data/issue/242/spec.json
new file mode 100644
index 0000000..5321bb9
--- /dev/null
+++ b/tests/data/issue/242/spec.json
@@ -0,0 +1,41 @@
+{
+  "openapi": "3.0.0",
+  "info": {
+    "title": "My API",
+    "version": "1, 2"
+  },
+  "paths": {
+    "/v1/users/profile": {
+      "get": {
+        "operationId": "V1GetUserProfile",
+        "summary": "Returns the user profile",
+        "responses": {
+          "200": {
+            "description": "dummy"
+          }
+        },
+        "security": [
+          {
+            "test_test": ["test:scope:foo"]
+          }
+        ]
+      }
+    }
+  },
+  "components": {
+    "securitySchemes": {
+      "test_test": {
+        "type": "oauth2",
+        "flows": {
+          "authorizationCode": {
+            "authorizationUrl": "https://example.com/openid-connect/auth",
+            "tokenUrl": "https://example.com/openid-connect/token",
+            "scopes": {
+              "test:scope:foo": "test_scope"
+            }
+          }
+        }
+      }
+    }
+  }
+}
\ No newline at end of file
diff --git a/tests/data/issue/242/spec2.json b/tests/data/issue/242/spec2.json
new file mode 100644
index 0000000..331d865
--- /dev/null
+++ b/tests/data/issue/242/spec2.json
@@ -0,0 +1,45 @@
+{
+  "openapi": "3.0.0",
+  "info": {
+    "title": "API Documentation",
+    "description": "All API endpoints are presented here.",
+    "version": "1.0.0"
+  },
+  "servers": [
+    {
+      "url": "http://127.0.0.1:8080/"
+    }
+  ],
+  "paths": {
+    "/endpoint": {
+      "get": {
+        "responses": {
+          "200": {
+            "description": "OK"
+          }
+        },
+        "security": [
+          {
+            "apiKey": [],
+            "bearerAuth": []
+          }
+        ]
+      }
+    }
+  },
+  "components": {
+    "securitySchemes": {
+      "apiKey": {
+        "type": "apiKey",
+        "in": "header",
+        "name": "X-APi-Key"
+      },
+      "bearerAuth": {
+        "type": "http",
+        "scheme": "bearer",
+        "bearerFormat": "JWT",
+        "description": "JWT Authorization header using the Bearer scheme."
+      }
+    }
+  }
+}
\ No newline at end of file
diff --git a/tests/data/issue/242/spec2.yml b/tests/data/issue/242/spec2.yml
new file mode 100644
index 0000000..eebe517
--- /dev/null
+++ b/tests/data/issue/242/spec2.yml
@@ -0,0 +1,31 @@
+# https://github.com/cebe/php-openapi/issues/242#issuecomment-2886431173
+openapi: 3.0.0
+info:
+  title: API Documentation
+  description: All API endpoints are presented here.
+  version: 1.0.0
+servers:
+  - url: http://127.0.0.1:8080/
+
+paths:
+
+  /endpoint:
+    get:
+      responses:
+        '200':
+          description: OK
+      security:
+        - apiKey: []
+          bearerAuth: []
+components:
+  securitySchemes:
+    apiKey:
+      type: apiKey
+      in: header
+      name: X-APi-Key
+    bearerAuth:
+      type: http
+      scheme: bearer
+      bearerFormat: JWT
+      description: JWT Authorization header using the Bearer scheme.
+
diff --git a/tests/issues/238/Issue238Test.php b/tests/issues/238/Issue238Test.php
new file mode 100644
index 0000000..530bd48
--- /dev/null
+++ b/tests/issues/238/Issue238Test.php
@@ -0,0 +1,137 @@
+<?php
+
+use cebe\openapi\Reader;
+use cebe\openapi\spec\OpenApi;
+use cebe\openapi\spec\SecurityRequirements;
+use cebe\openapi\Writer;
+
+// https://github.com/cebe/php-openapi/issues/238
+class Issue238Test extends \PHPUnit\Framework\TestCase
+{
+    public function test238AddSupportForEmptySecurityRequirementObjectInSecurityRequirementRead()
+    {
+        $openapi = Reader::readFromYamlFile(dirname(dirname(__DIR__)).'/data/issue/238/spec.yml');
+        $this->assertInstanceOf(\cebe\openapi\SpecObjectInterface::class, $openapi);
+        $this->assertInstanceOf(\cebe\openapi\spec\SecurityRequirements::class, $openapi->paths->getPath('/path-secured')->getOperations()['get']->security);
+        $this->assertSame(json_decode(json_encode($openapi->paths->getPath('/path-secured')->getOperations()['get']->security->getSerializableData()), true), [[]]);
+
+        $openapiJson = Reader::readFromJson(<<<JSON
+        {
+  "openapi": "3.0.0",
+  "info": {
+    "title": "Secured API",
+    "version": "1.0.0"
+  },
+  "paths": {
+    "/global-secured": {
+      "get": {
+        "responses": {
+          "200": {
+            "description": "OK"
+          }
+        }
+      }
+    },
+    "/path-secured": {
+      "get": {
+        "security": [
+          {}
+        ],
+        "responses": {
+          "200": {
+            "description": "OK"
+          }
+        }
+      }
+    }
+  },
+  "components": {
+    "securitySchemes": {
+      "ApiKeyAuth": {
+        "type": "apiKey",
+        "in": "header",
+        "name": "X-API-Key"
+      },
+      "BearerAuth": {
+        "type": "http",
+        "scheme": "bearer"
+      }
+    }
+  },
+  "security": [
+    {
+      "ApiKeyAuth": []
+    }
+  ]
+}
+
+JSON
+);
+
+        $this->assertInstanceOf(\cebe\openapi\SpecObjectInterface::class, $openapiJson);
+        $this->assertInstanceOf(\cebe\openapi\spec\SecurityRequirements::class, $openapiJson->paths->getPath('/path-secured')->getOperations()['get']->security);
+        $this->assertSame(json_decode(json_encode($openapiJson->paths->getPath('/path-secured')->getOperations()['get']->security->getSerializableData()), true), [[]]);
+    }
+
+    public function test238AddSupportForEmptySecurityRequirementObjectInSecurityRequirementWrite()
+    {
+        $openapi = $this->createOpenAPI([
+            'security' => new SecurityRequirements([
+                []
+            ]),
+        ]);
+
+        $yaml = Writer::writeToYaml($openapi);
+
+        $this->assertEquals(preg_replace('~\R~', "\n", <<<YAML
+openapi: 3.0.0
+info:
+  title: 'Test API'
+  version: 1.0.0
+paths: {  }
+security:
+  - {  }
+
+YAML
+        ),
+            $yaml
+        );
+
+        $openapiJson = $this->createOpenAPI([
+            'security' => new SecurityRequirements([
+                []
+            ]),
+        ]);
+
+        $json = Writer::writeToJson($openapiJson);
+
+        $this->assertEquals(preg_replace('~\R~', "\n", <<<JSON
+{
+    "openapi": "3.0.0",
+    "info": {
+        "title": "Test API",
+        "version": "1.0.0"
+    },
+    "paths": {},
+    "security": [
+        {}
+    ]
+}
+JSON
+        ),
+            $json
+        );
+    }
+
+    private function createOpenAPI($merge = [])
+    {
+        return new OpenApi(array_merge([
+            'openapi' => '3.0.0',
+            'info' => [
+                'title' => 'Test API',
+                'version' => '1.0.0',
+            ],
+            'paths' => [],
+        ], $merge));
+    }
+}
diff --git a/tests/issues/242/Issue242Test.php b/tests/issues/242/Issue242Test.php
new file mode 100644
index 0000000..7ab89cc
--- /dev/null
+++ b/tests/issues/242/Issue242Test.php
@@ -0,0 +1,283 @@
+<?php
+
+use cebe\openapi\Reader;
+use cebe\openapi\spec\Components;
+use cebe\openapi\spec\SecurityRequirement;
+use cebe\openapi\spec\SecurityRequirements;
+use cebe\openapi\spec\SecurityScheme;
+use cebe\openapi\SpecObjectInterface;
+use cebe\openapi\Writer;
+use PHPUnit\Framework\TestCase;
+
+// https://github.com/cebe/php-openapi/issues/242
+class Issue242Test extends TestCase
+{
+    public function test242CliCallToOpenapiSpecWithSecurityInPathFails()
+    {
+        $file = dirname(__DIR__, 2) . '/data/issue/242/spec.json';
+        $openapi = Reader::readFromJsonFile($file);
+        $this->assertInstanceOf(SpecObjectInterface::class, $openapi);
+
+        $dirSep = DIRECTORY_SEPARATOR;
+        $cmd = 'php ' . dirname(__DIR__, 3) . "{$dirSep}bin{$dirSep}php-openapi validate " . $file . " 2>&1";
+        exec($cmd, $op, $ec);
+        $this->assertSame($this->removeCliFormatting($op[0]), 'The supplied API Description validates against the OpenAPI v3.0 schema.');
+        $this->assertSame(0, $ec);
+    }
+
+    private function removeCliFormatting($string)
+    {
+        // Regex to remove ANSI escape codes
+        return preg_replace('/\e\[[0-9;]*m/', '', $string);
+    }
+
+    public function test242Case2() # https://github.com/cebe/php-openapi/issues/242#issuecomment-2886431173
+    {
+        // read in yml
+        $file = dirname(__DIR__, 2) . '/data/issue/242/spec2.yml';
+        $openapi = Reader::readFromYamlFile($file);
+        $this->assertInstanceOf(SpecObjectInterface::class, $openapi);
+        $this->assertSame(json_decode(json_encode($openapi->paths['/endpoint']->get->security->getSerializableData()), true), [
+            [
+                'apiKey' => [],
+                'bearerAuth' => []
+            ]
+        ]);
+
+        # write back to yml
+        $yaml = Writer::writeToYaml($openapi);
+        $this->assertEquals(preg_replace('~\R~', "\n", <<<YAML
+openapi: 3.0.0
+info:
+  title: 'API Documentation'
+  description: 'All API endpoints are presented here.'
+  version: 1.0.0
+servers:
+  -
+    url: 'http://127.0.0.1:8080/'
+paths:
+  /endpoint:
+    get:
+      responses:
+        '200':
+          description: OK
+      security:
+        -
+          apiKey: []
+          bearerAuth: []
+components:
+  securitySchemes:
+    apiKey:
+      type: apiKey
+      name: X-APi-Key
+      in: header
+    bearerAuth:
+      type: http
+      description: 'JWT Authorization header using the Bearer scheme.'
+      scheme: bearer
+      bearerFormat: JWT
+
+YAML
+        ),
+            $yaml
+        );
+
+        // read in json
+        $file = dirname(__DIR__, 2) . '/data/issue/242/spec2.json';
+        $openapi = Reader::readFromJsonFile($file);
+        $this->assertInstanceOf(SpecObjectInterface::class, $openapi);
+        $this->assertSame(json_decode(json_encode($openapi->paths['/endpoint']->get->security->getSerializableData()), true), [
+            [
+                'apiKey' => [],
+                'bearerAuth' => []
+            ]
+        ]);
+
+        // write back in json
+        $yaml = Writer::writeToJson($openapi);
+        $this->assertEquals(preg_replace('~\R~', "\n", <<<JSON
+{
+    "openapi": "3.0.0",
+    "info": {
+        "title": "API Documentation",
+        "description": "All API endpoints are presented here.",
+        "version": "1.0.0"
+    },
+    "servers": [
+        {
+            "url": "http:\/\/127.0.0.1:8080\/"
+        }
+    ],
+    "paths": {
+        "\/endpoint": {
+            "get": {
+                "responses": {
+                    "200": {
+                        "description": "OK"
+                    }
+                },
+                "security": [
+                    {
+                        "apiKey": [],
+                        "bearerAuth": []
+                    }
+                ]
+            }
+        }
+    },
+    "components": {
+        "securitySchemes": {
+            "apiKey": {
+                "type": "apiKey",
+                "name": "X-APi-Key",
+                "in": "header"
+            },
+            "bearerAuth": {
+                "type": "http",
+                "description": "JWT Authorization header using the Bearer scheme.",
+                "scheme": "bearer",
+                "bearerFormat": "JWT"
+            }
+        }
+    }
+}
+JSON
+        ),
+            $yaml
+        );
+    }
+
+    public function test242Case3MultipleAuth()
+    {
+        $file = dirname(__DIR__, 2) . '/data/issue/242/multiple_auth.yml';
+        $openapi = Reader::readFromYamlFile($file);
+        $this->assertInstanceOf(SpecObjectInterface::class, $openapi);
+        $act = json_decode(json_encode($openapi->security->getSerializableData()), true);
+        $this->assertSame([], $act[0]['BasicAuth']);
+
+        # write back to yml
+        $yaml = Writer::writeToYaml($openapi);
+        $this->assertEquals(preg_replace('~\R~', "\n", <<<YAML
+openapi: 3.0.0
+info:
+  title: 'Multiple auth'
+  version: 1.0.0
+paths: {  }
+components:
+  securitySchemes:
+    BasicAuth:
+      type: http
+      scheme: basic
+    BearerAuth:
+      type: http
+      scheme: bearer
+    ApiKeyAuth:
+      type: apiKey
+      name: X-API-Key
+      in: header
+    OpenID:
+      type: openIdConnect
+      openIdConnectUrl: 'https://example.com/.well-known/openid-configuration'
+    OAuth2:
+      type: oauth2
+      flows:
+        authorizationCode:
+          authorizationUrl: 'https://example.com/oauth/authorize'
+          tokenUrl: 'https://example.com/oauth/token'
+          scopes:
+            read: 'Grants read access'
+            write: 'Grants write access'
+            admin: 'Grants access to admin operations'
+security:
+  -
+    BasicAuth: []
+    BearerAuth: []
+  -
+    ApiKeyAuth: []
+    OAuth2:
+      - read
+
+YAML
+        ),
+            $yaml
+        );
+    }
+
+    public function test242Case4WriteMultipleAuth()
+    {
+        $openapi = $this->createOpenAPI([
+            'components' => new Components([
+                'securitySchemes' => [
+                    'BearerAuth' => new SecurityScheme([
+                        'type' => 'http',
+                        'scheme' => 'bearer',
+                    ]),
+                    'BasicAuth' => new SecurityScheme([
+                        'type' => 'http',
+                        'scheme' => 'basic',
+                    ]),
+                    'ApiKeyAuth' => new SecurityScheme([
+                        'type' => 'apiKey',
+                        'name' => 'X-API-Key',
+                        'in' => 'header'
+                    ])
+                ],
+            ]),
+            'security' => new SecurityRequirements([
+                [
+                    'BearerAuth' => new SecurityRequirement([]),
+                    'BasicAuth' => new SecurityRequirement([])
+                ],
+                [
+                    'ApiKeyAuth' => new SecurityRequirement([])
+                ]
+            ]),
+            'paths' => [],
+        ]);
+
+
+        $yaml = \cebe\openapi\Writer::writeToYaml($openapi);
+
+        $this->assertEquals(preg_replace('~\R~', "\n", <<<YAML
+openapi: 3.0.0
+info:
+  title: 'Test API'
+  version: 1.0.0
+paths: {  }
+components:
+  securitySchemes:
+    BearerAuth:
+      type: http
+      scheme: bearer
+    BasicAuth:
+      type: http
+      scheme: basic
+    ApiKeyAuth:
+      type: apiKey
+      name: X-API-Key
+      in: header
+security:
+  -
+    BearerAuth: []
+    BasicAuth: []
+  -
+    ApiKeyAuth: []
+
+YAML
+        ),
+            $yaml
+        );
+    }
+
+    private function createOpenAPI($merge = [])
+    {
+        return new \cebe\openapi\spec\OpenApi(array_merge([
+            'openapi' => '3.0.0',
+            'info' => [
+                'title' => 'Test API',
+                'version' => '1.0.0',
+            ],
+            'paths' => [],
+        ], $merge));
+    }
+}
diff --git a/tests/spec/OpenApiTest.php b/tests/spec/OpenApiTest.php
index 433bd35..7999dae 100644
--- a/tests/spec/OpenApiTest.php
+++ b/tests/spec/OpenApiTest.php
@@ -88,6 +88,21 @@ public function assertAllInstanceOf($className, $array)
         }
     }
 
+    public function assertFewInstanceOf($className, $array)
+    {
+        foreach($array as $k => $v) {
+            if (is_numeric($k) && $v === []) { # https://github.com/cebe/php-openapi/issues/238
+                continue;
+            }
+
+            if (is_array($v)) {
+                $this->{__FUNCTION__}($className, $v);
+            } else {
+                $this->assertInstanceOf($className, $v, "Asserting that item with key '$k' is instance of $className");
+            }
+        }
+    }
+
     public function specProvider()
     {
         // examples from https://github.com/OAI/OpenAPI-Specification/tree/master/examples/v3.0
@@ -222,7 +237,7 @@ public function testSpecs($openApiFile)
 
         // security
         $openapi->security !== null && $this->assertInstanceOf(\cebe\openapi\spec\SecurityRequirements::class, $openapi->security);
-        $openapi->security !== null && $this->assertAllInstanceOf(\cebe\openapi\spec\SecurityRequirement::class, $openapi->security->getRequirements());
+        $openapi->security !== null && $this->assertFewInstanceOf(\cebe\openapi\spec\SecurityRequirement::class, $openapi->security->getRequirements());
 
         // tags
         $this->assertAllInstanceOf(\cebe\openapi\spec\Tag::class, $openapi->tags);