diff --git a/parameters/validate_security.go b/parameters/validate_security.go
index d2e6e9b..a886200 100644
--- a/parameters/validate_security.go
+++ b/parameters/validate_security.go
@@ -10,9 +10,9 @@ import (
 
 	"github.com/pb33f/libopenapi-validator/errors"
 	"github.com/pb33f/libopenapi-validator/helpers"
+	"github.com/pb33f/libopenapi-validator/paths"
 	v3 "github.com/pb33f/libopenapi/datamodel/high/v3"
 	"github.com/pb33f/libopenapi/orderedmap"
-	"github.com/pb33f/libopenapi-validator/paths"
 )
 
 func (v *paramValidator) ValidateSecurity(request *http.Request) (bool, []*errors.ValidationError) {
@@ -44,7 +44,13 @@ func (v *paramValidator) ValidateSecurityWithPathItem(request *http.Request, pat
 		return true, nil
 	}
 
+	allErrors := []*errors.ValidationError{}
+
 	for _, sec := range security {
+		if sec.ContainsEmptyRequirement {
+			return true, nil
+		}
+
 		for pair := orderedmap.First(sec.Requirements); pair != nil; pair = pair.Next() {
 			secName := pair.Key()
 
@@ -85,8 +91,9 @@ func (v *paramValidator) ValidateSecurityWithPathItem(request *http.Request, pat
 						}
 
 						errors.PopulateValidationErrors(validationErrors, request, pathValue)
-
-						return false, validationErrors
+						allErrors = append(allErrors, validationErrors...)
+					} else {
+						return true, nil
 					}
 				}
 
@@ -107,8 +114,9 @@ func (v *paramValidator) ValidateSecurityWithPathItem(request *http.Request, pat
 						}
 
 						errors.PopulateValidationErrors(validationErrors, request, pathValue)
-
-						return false, validationErrors
+						allErrors = append(allErrors, validationErrors...)
+					} else {
+						return true, nil
 					}
 				}
 				if secScheme.In == "query" {
@@ -133,8 +141,9 @@ func (v *paramValidator) ValidateSecurityWithPathItem(request *http.Request, pat
 						}
 
 						errors.PopulateValidationErrors(validationErrors, request, pathValue)
-
-						return false, validationErrors
+						allErrors = append(allErrors, validationErrors...)
+					} else {
+						return true, nil
 					}
 				}
 				if secScheme.In == "cookie" {
@@ -160,12 +169,14 @@ func (v *paramValidator) ValidateSecurityWithPathItem(request *http.Request, pat
 						}
 
 						errors.PopulateValidationErrors(validationErrors, request, pathValue)
-
-						return false, validationErrors
+						allErrors = append(allErrors, validationErrors...)
+					} else {
+						return true, nil
 					}
 				}
 			}
 		}
 	}
-	return true, nil
+
+	return false, allErrors
 }
diff --git a/parameters/validate_security_test.go b/parameters/validate_security_test.go
index 2d68164..121ad58 100644
--- a/parameters/validate_security_test.go
+++ b/parameters/validate_security_test.go
@@ -4,11 +4,12 @@
 package parameters
 
 import (
+	"net/http"
+	"testing"
+
 	"github.com/pb33f/libopenapi"
 	"github.com/pb33f/libopenapi-validator/paths"
 	"github.com/stretchr/testify/assert"
-	"net/http"
-	"testing"
 )
 
 func TestParamValidator_ValidateSecurity_APIKeyHeader_NotFound(t *testing.T) {
@@ -398,3 +399,119 @@ paths:
 	assert.Len(t, errors, 1)
 	assert.Equal(t, "POST Path '/beef' not found", errors[0].Message)
 }
+
+func TestParamValidator_ValidateSecurity_MultipleSecurity(t *testing.T) {
+
+	spec := `openapi: 3.1.0
+paths:
+  /products:
+    post:
+      security:
+        - ApiKeyAuthQuery:
+          - write:products
+        - ApiKeyAuthHeader:
+          - write:products
+components:
+  securitySchemes:
+    ApiKeyAuthQuery:
+      type: apiKey
+      in: query
+      name: X-API-Key
+    ApiKeyAuthHeader:
+      type: apiKey
+      in: header
+      name: X-API-Key
+`
+
+	doc, _ := libopenapi.NewDocument([]byte(spec))
+
+	m, _ := doc.BuildV3Model()
+
+	v := NewParameterValidator(&m.Model)
+
+	request, _ := http.NewRequest(http.MethodPost, "https://things.com/products", nil)
+	request.Header.Add("X-API-Key", "1234")
+
+	valid, errors := v.ValidateSecurity(request)
+	assert.True(t, valid)
+	assert.Equal(t, 0, len(errors))
+}
+
+func TestParamValidator_ValidateSecurity_MultipleSecurity_EmptyOption(t *testing.T) {
+
+	spec := `openapi: 3.1.0
+paths:
+  /products:
+    post:
+      security:
+        - ApiKeyAuth:
+          - write:products
+        - {}
+components:
+  securitySchemes:
+    ApiKeyAuth:
+      type: apiKey
+      in: header
+      name: X-API-Key
+`
+
+	doc, _ := libopenapi.NewDocument([]byte(spec))
+
+	m, _ := doc.BuildV3Model()
+
+	v := NewParameterValidator(&m.Model)
+
+	request, _ := http.NewRequest(http.MethodPost, "https://things.com/products", nil)
+
+	valid, errors := v.ValidateSecurity(request)
+	assert.True(t, valid)
+	assert.Equal(t, 0, len(errors))
+}
+
+func TestParamValidator_ValidateSecurity_MultipleSecurity_NotFound(t *testing.T) {
+
+	spec := `openapi: 3.1.0
+paths:
+  /products:
+    post:
+      security:
+        - ApiKeyAuthQuery:
+          - write:products
+        - ApiKeyAuthHeader:
+          - write:products
+components:
+  securitySchemes:
+    ApiKeyAuthQuery:
+      type: apiKey
+      in: query
+      name: X-API-Key
+    ApiKeyAuthHeader:
+      type: apiKey
+      in: header
+      name: X-API-Key
+`
+
+	doc, _ := libopenapi.NewDocument([]byte(spec))
+
+	m, _ := doc.BuildV3Model()
+
+	v := NewParameterValidator(&m.Model)
+
+	request, _ := http.NewRequest(http.MethodPost, "https://things.com/products", nil)
+
+	valid, errors := v.ValidateSecurity(request)
+	assert.False(t, valid)
+	assert.Equal(t, 2, len(errors))
+
+	assert.Equal(t, "API Key X-API-Key not found in query", errors[0].Message)
+	assert.Equal(t, "Add an API Key via 'X-API-Key' to the query string of the URL, "+
+		"for example 'https://things.com/products?X-API-Key=your-api-key'", errors[0].HowToFix)
+	assert.Equal(t, request.Method, errors[0].RequestMethod)
+	assert.Equal(t, request.URL.Path, errors[0].RequestPath)
+	assert.Equal(t, "/products", errors[0].SpecPath)
+
+	assert.Equal(t, "API Key X-API-Key not found in header", errors[1].Message)
+	assert.Equal(t, request.Method, errors[1].RequestMethod)
+	assert.Equal(t, request.URL.Path, errors[1].RequestPath)
+	assert.Equal(t, "/products", errors[1].SpecPath)
+}