diff --git a/examples/extensions/extensions.spec.js b/examples/extensions/extensions.spec.js
index 4479cbae..7001a7fc 100644
--- a/examples/extensions/extensions.spec.js
+++ b/examples/extensions/extensions.spec.js
@@ -1,8 +1,9 @@
 const swaggerJsdoc = require('../..');
-const referenceSpecification = require('./reference-specification.json');
+const webhooksSingleSpecification = require('./x-webhooks-single-reference-specification.json');
+const webhooksMultipleSpecification = require('./x-webhooks-multiple-reference-specification.json');
 
 describe('Example for using extensions', () => {
-  it('should support x-webhooks', () => {
+  it('should support single entry in x-webhooks', () => {
     const result = swaggerJsdoc({
       swaggerDefinition: {
         info: {
@@ -10,8 +11,21 @@ describe('Example for using extensions', () => {
           version: '0.0.1',
         },
       },
-      apis: ['./examples/extensions/example.js'],
+      apis: ['./examples/extensions/x-webhooks-single.js'],
     });
-    expect(result).toEqual(referenceSpecification);
+    expect(result).toEqual(webhooksSingleSpecification);
+  });
+
+  it('should support multiple entries in x-webhooks', () => {
+    const result = swaggerJsdoc({
+      swaggerDefinition: {
+        info: {
+          title: 'Example with extensions',
+          version: '0.0.1',
+        },
+      },
+      apis: ['./examples/extensions/x-webhooks-multiple.js'],
+    });
+    expect(result).toEqual(webhooksMultipleSpecification);
   });
 });
diff --git a/examples/extensions/x-webhooks-multiple-reference-specification.json b/examples/extensions/x-webhooks-multiple-reference-specification.json
new file mode 100644
index 00000000..6f7d73d5
--- /dev/null
+++ b/examples/extensions/x-webhooks-multiple-reference-specification.json
@@ -0,0 +1,48 @@
+{
+  "info": { "title": "Example with extensions", "version": "0.0.1" },
+  "swagger": "2.0",
+  "paths": {},
+  "definitions": {},
+  "responses": {},
+  "parameters": {},
+  "securityDefinitions": {},
+  "tags": [],
+  "x-webhooks": {
+    "newCat": {
+      "post": {
+        "description": "Information about a new cat in the systems",
+        "tags": ["pet"],
+        "requestBody": {
+          "content": {
+            "application/json": {
+              "schema": { "$ref": "#/components/schemas/Cat" }
+            }
+          }
+        },
+        "responses": {
+          "200": {
+            "description": "Return a 200 status to indicate that the data was received successfully"
+          }
+        }
+      }
+    },
+    "newDog": {
+      "post": {
+        "description": "Information about a new dog in the systems",
+        "tags": ["pet"],
+        "requestBody": {
+          "content": {
+            "application/json": {
+              "schema": { "$ref": "#/components/schemas/Dog" }
+            }
+          }
+        },
+        "responses": {
+          "200": {
+            "description": "Return a 200 status to indicate that the data was received successfully"
+          }
+        }
+      }
+    }
+  }
+}
diff --git a/examples/extensions/x-webhooks-multiple.js b/examples/extensions/x-webhooks-multiple.js
new file mode 100644
index 00000000..eacf9b33
--- /dev/null
+++ b/examples/extensions/x-webhooks-multiple.js
@@ -0,0 +1,41 @@
+/* istanbul ignore file */
+
+/**
+ * Example of cat
+ *
+ * @swagger
+ * x-webhooks:
+ *  newCat:
+ *    post:
+ *      description: Information about a new cat in the systems
+ *      tags:
+ *        - pet
+ *      requestBody:
+ *        content:
+ *          application/json:
+ *            schema:
+ *              $ref: "#/components/schemas/Cat"
+ *      responses:
+ *        "200":
+ *          description: Return a 200 status to indicate that the data was received successfully
+ */
+
+/**
+ * Example of dog
+ *
+ * @swagger
+ * x-webhooks:
+ *  newDog:
+ *    post:
+ *      description: Information about a new dog in the systems
+ *      tags:
+ *        - pet
+ *      requestBody:
+ *        content:
+ *          application/json:
+ *            schema:
+ *              $ref: "#/components/schemas/Dog"
+ *      responses:
+ *        "200":
+ *          description: Return a 200 status to indicate that the data was received successfully
+ */
diff --git a/examples/extensions/reference-specification.json b/examples/extensions/x-webhooks-single-reference-specification.json
similarity index 100%
rename from examples/extensions/reference-specification.json
rename to examples/extensions/x-webhooks-single-reference-specification.json
diff --git a/examples/extensions/example.js b/examples/extensions/x-webhooks-single.js
similarity index 100%
rename from examples/extensions/example.js
rename to examples/extensions/x-webhooks-single.js
diff --git a/src/specification.js b/src/specification.js
index bf0dedb1..9eaf1172 100644
--- a/src/specification.js
+++ b/src/specification.js
@@ -128,7 +128,10 @@ function organize(swaggerObject, annotation, property) {
   // Root property on purpose.
   // @see https://github.com/OAI/OpenAPI-Specification/blob/master/proposals/002_Webhooks.md#proposed-solution
   if (property === 'x-webhooks') {
-    swaggerObject[property] = annotation[property];
+    swaggerObject[property] = mergeDeep(
+      swaggerObject[property],
+      annotation[property]
+    );
   }
 
   // Other extensions can be in varying places depending on different vendors and opinions.