diff --git a/cmds/swagger.js b/cmds/swagger.js
index 09e78ab49..52a336d44 100644
--- a/cmds/swagger.js
+++ b/cmds/swagger.js
@@ -80,7 +80,8 @@ exports.run = async function(opts) {
 
     function error(err) {
       try {
-        return Promise.reject(new Error(JSON.parse(err.error).description));
+        const parsedError = JSON.parse(err.error);
+        return Promise.reject(new Error(parsedError.description || parsedError.error));
       } catch (e) {
         return Promise.reject(new Error('There was an error uploading!'));
       }
diff --git a/test/cmds/swagger.test.js b/test/cmds/swagger.test.js
index 2254f7d21..686e0f866 100644
--- a/test/cmds/swagger.test.js
+++ b/test/cmds/swagger.test.js
@@ -66,6 +66,23 @@ describe('rdme swagger', () => {
       .then(() => mock.done());
   });
 
+  it('should properly bubble up validation error if invalid swagger is uploaded', () => {
+    const mock = nock(config.host)
+      .get(`/api/v1/version/${version}`)
+      .basicAuth({ user: key })
+      .reply(200, { version: '1.0.0' })
+      .post('/api/v1/api-specification', body => body.match('form-data; name="spec"'))
+      .delayConnection(1000)
+      .basicAuth({ user: key })
+      .reply(500, {
+        error: 'README VALIDATION ERROR "x-samples-languages" must be of type "Array"',
+      });
+
+    return expect(swagger.run({ spec: './test/fixtures/invalid-swagger.json', key, version }))
+      .rejects.toThrow('README VALIDATION ERROR "x-samples-languages" must be of type "Array"')
+      .then(() => mock.done());
+  });
+
   it('should return a 404 if version flag not found', () => {});
 
   it('should request a version list if version is not found', () => {
diff --git a/test/fixtures/invalid-swagger.json b/test/fixtures/invalid-swagger.json
new file mode 100644
index 000000000..9f5ef7023
--- /dev/null
+++ b/test/fixtures/invalid-swagger.json
@@ -0,0 +1,1036 @@
+{
+  "swagger": "2.0",
+  "info": {
+    "description": "This is a sample server Petstore server.  You can find out more about Swagger at [http://swagger.io](http://swagger.io) or on [irc.freenode.net, #swagger](http://swagger.io/irc/).  For this sample, you can use the api key `special-key` to test the authorization filters.",
+    "version": "1.0.0",
+    "title": "Swagger Petstore",
+    "termsOfService": "http://swagger.io/terms/",
+    "contact": {
+      "email": "apiteam@swagger.io"
+    },
+    "license": {
+      "name": "Apache 2.0",
+      "url": "http://www.apache.org/licenses/LICENSE-2.0.html"
+    }
+  },
+  "host": "petstore.swagger.io",
+  "basePath": "/v2",
+  "tags": [
+    {
+      "name": "pet",
+      "description": "Everything about your Pets",
+      "externalDocs": {
+        "description": "Find out more",
+        "url": "http://swagger.io"
+      }
+    },
+    {
+      "name": "store",
+      "description": "Access to Petstore orders"
+    },
+    {
+      "name": "user",
+      "description": "Operations about user",
+      "externalDocs": {
+        "description": "Find out more about our store",
+        "url": "http://swagger.io"
+      }
+    }
+  ],
+  "schemes": [
+    "http"
+  ],
+  "paths": {
+    "/pet": {
+      "post": {
+        "tags": [
+          "pet"
+        ],
+        "summary": "Add a new pet to the store",
+        "description": "",
+        "operationId": "addPet",
+        "consumes": [
+          "application/json",
+          "application/xml"
+        ],
+        "produces": [
+          "application/xml",
+          "application/json"
+        ],
+        "parameters": [
+          {
+            "in": "body",
+            "name": "body",
+            "description": "Pet object that needs to be added to the store",
+            "required": true,
+            "schema": {
+              "$ref": "#/definitions/Pet"
+            }
+          }
+        ],
+        "responses": {
+          "405": {
+            "description": "Invalid input"
+          }
+        },
+        "security": [
+          {
+            "petstore_auth": [
+              "write:pets",
+              "read:pets"
+            ]
+          }
+        ]
+      },
+      "put": {
+        "tags": [
+          "pet"
+        ],
+        "summary": "Update an existing pet",
+        "description": "",
+        "operationId": "updatePet",
+        "consumes": [
+          "application/json",
+          "application/xml"
+        ],
+        "produces": [
+          "application/xml",
+          "application/json"
+        ],
+        "parameters": [
+          {
+            "in": "body",
+            "name": "body",
+            "description": "Pet object that needs to be added to the store",
+            "required": true,
+            "schema": {
+              "$ref": "#/definitions/Pet"
+            }
+          }
+        ],
+        "responses": {
+          "400": {
+            "description": "Invalid ID supplied"
+          },
+          "404": {
+            "description": "Pet not found"
+          },
+          "405": {
+            "description": "Validation exception"
+          }
+        },
+        "security": [
+          {
+            "petstore_auth": [
+              "write:pets",
+              "read:pets"
+            ]
+          }
+        ]
+      }
+    },
+    "/pet/findByStatus": {
+      "get": {
+        "tags": [
+          "pet"
+        ],
+        "summary": "Finds Pets by status",
+        "description": "Multiple status values can be provided with comma separated strings",
+        "operationId": "findPetsByStatus",
+        "produces": [
+          "application/xml",
+          "application/json"
+        ],
+        "parameters": [
+          {
+            "name": "status",
+            "in": "query",
+            "description": "Status values that need to be considered for filter",
+            "required": true,
+            "type": "array",
+            "items": {
+              "type": "string",
+              "enum": [
+                "available",
+                "pending",
+                "sold"
+              ],
+              "default": "available"
+            },
+            "collectionFormat": "multi"
+          }
+        ],
+        "responses": {
+          "200": {
+            "description": "successful operation",
+            "schema": {
+              "type": "array",
+              "items": {
+                "$ref": "#/definitions/Pet"
+              }
+            }
+          },
+          "400": {
+            "description": "Invalid status value"
+          }
+        },
+        "security": [
+          {
+            "petstore_auth": [
+              "write:pets",
+              "read:pets"
+            ]
+          }
+        ]
+      }
+    },
+    "/pet/findByTags": {
+      "get": {
+        "tags": [
+          "pet"
+        ],
+        "summary": "Finds Pets by tags",
+        "description": "Muliple tags can be provided with comma separated strings. Use tag1, tag2, tag3 for testing.",
+        "operationId": "findPetsByTags",
+        "produces": [
+          "application/xml",
+          "application/json"
+        ],
+        "parameters": [
+          {
+            "name": "tags",
+            "in": "query",
+            "description": "Tags to filter by",
+            "required": true,
+            "type": "array",
+            "items": {
+              "type": "string"
+            },
+            "collectionFormat": "multi"
+          }
+        ],
+        "responses": {
+          "200": {
+            "description": "successful operation",
+            "schema": {
+              "type": "array",
+              "items": {
+                "$ref": "#/definitions/Pet"
+              }
+            }
+          },
+          "400": {
+            "description": "Invalid tag value"
+          }
+        },
+        "security": [
+          {
+            "petstore_auth": [
+              "write:pets",
+              "read:pets"
+            ]
+          }
+        ],
+        "deprecated": true
+      }
+    },
+    "/pet/{petId}": {
+      "get": {
+        "tags": [
+          "pet"
+        ],
+        "summary": "Find pet by ID",
+        "description": "Returns a single pet",
+        "operationId": "getPetById",
+        "produces": [
+          "application/xml",
+          "application/json"
+        ],
+        "parameters": [
+          {
+            "name": "petId",
+            "in": "path",
+            "description": "ID of pet to return",
+            "required": true,
+            "type": "integer",
+            "format": "int64"
+          }
+        ],
+        "responses": {
+          "200": {
+            "description": "successful operation",
+            "schema": {
+              "$ref": "#/definitions/Pet"
+            }
+          },
+          "400": {
+            "description": "Invalid ID supplied"
+          },
+          "404": {
+            "description": "Pet not found"
+          }
+        },
+        "security": [
+          {
+            "api_key": []
+          }
+        ]
+      },
+      "post": {
+        "tags": [
+          "pet"
+        ],
+        "summary": "Updates a pet in the store with form data",
+        "description": "",
+        "operationId": "updatePetWithForm",
+        "consumes": [
+          "application/x-www-form-urlencoded"
+        ],
+        "produces": [
+          "application/xml",
+          "application/json"
+        ],
+        "parameters": [
+          {
+            "name": "petId",
+            "in": "path",
+            "description": "ID of pet that needs to be updated",
+            "required": true,
+            "type": "integer",
+            "format": "int64"
+          },
+          {
+            "name": "name",
+            "in": "formData",
+            "description": "Updated name of the pet",
+            "required": false,
+            "type": "string"
+          },
+          {
+            "name": "status",
+            "in": "formData",
+            "description": "Updated status of the pet",
+            "required": false,
+            "type": "string"
+          }
+        ],
+        "responses": {
+          "405": {
+            "description": "Invalid input"
+          }
+        },
+        "security": [
+          {
+            "petstore_auth": [
+              "write:pets",
+              "read:pets"
+            ]
+          }
+        ]
+      },
+      "delete": {
+        "tags": [
+          "pet"
+        ],
+        "summary": "Deletes a pet",
+        "description": "",
+        "operationId": "deletePet",
+        "produces": [
+          "application/xml",
+          "application/json"
+        ],
+        "parameters": [
+          {
+            "name": "api_key",
+            "in": "header",
+            "required": false,
+            "type": "string"
+          },
+          {
+            "name": "petId",
+            "in": "path",
+            "description": "Pet id to delete",
+            "required": true,
+            "type": "integer",
+            "format": "int64"
+          }
+        ],
+        "responses": {
+          "400": {
+            "description": "Invalid ID supplied"
+          },
+          "404": {
+            "description": "Pet not found"
+          }
+        },
+        "security": [
+          {
+            "petstore_auth": [
+              "write:pets",
+              "read:pets"
+            ]
+          }
+        ]
+      }
+    },
+    "/pet/{petId}/uploadImage": {
+      "post": {
+        "tags": [
+          "pet"
+        ],
+        "summary": "uploads an image",
+        "description": "",
+        "operationId": "uploadFile",
+        "consumes": [
+          "multipart/form-data"
+        ],
+        "produces": [
+          "application/json"
+        ],
+        "parameters": [
+          {
+            "name": "petId",
+            "in": "path",
+            "description": "ID of pet to update",
+            "required": true,
+            "type": "integer",
+            "format": "int64"
+          },
+          {
+            "name": "additionalMetadata",
+            "in": "formData",
+            "description": "Additional data to pass to server",
+            "required": false,
+            "type": "string"
+          },
+          {
+            "name": "file",
+            "in": "formData",
+            "description": "file to upload",
+            "required": false,
+            "type": "file"
+          }
+        ],
+        "responses": {
+          "200": {
+            "description": "successful operation",
+            "schema": {
+              "$ref": "#/definitions/ApiResponse"
+            }
+          }
+        },
+        "security": [
+          {
+            "petstore_auth": [
+              "write:pets",
+              "read:pets"
+            ]
+          }
+        ]
+      }
+    },
+    "/store/inventory": {
+      "get": {
+        "tags": [
+          "store"
+        ],
+        "summary": "Returns pet inventories by status",
+        "description": "Returns a map of status codes to quantities",
+        "operationId": "getInventory",
+        "produces": [
+          "application/json"
+        ],
+        "parameters": [],
+        "responses": {
+          "200": {
+            "description": "successful operation",
+            "schema": {
+              "type": "object",
+              "additionalProperties": {
+                "type": "integer",
+                "format": "int32"
+              }
+            }
+          }
+        },
+        "security": [
+          {
+            "api_key": []
+          }
+        ]
+      }
+    },
+    "/store/order": {
+      "post": {
+        "tags": [
+          "store"
+        ],
+        "summary": "Place an order for a pet",
+        "description": "",
+        "operationId": "placeOrder",
+        "produces": [
+          "application/xml",
+          "application/json"
+        ],
+        "parameters": [
+          {
+            "in": "body",
+            "name": "body",
+            "description": "order placed for purchasing the pet",
+            "required": true,
+            "schema": {
+              "$ref": "#/definitions/Order"
+            }
+          }
+        ],
+        "responses": {
+          "200": {
+            "description": "successful operation",
+            "schema": {
+              "$ref": "#/definitions/Order"
+            }
+          },
+          "400": {
+            "description": "Invalid Order"
+          }
+        }
+      }
+    },
+    "/store/order/{orderId}": {
+      "get": {
+        "tags": [
+          "store"
+        ],
+        "summary": "Find purchase order by ID",
+        "description": "For valid response try integer IDs with value >= 1 and <= 10. Other values will generated exceptions",
+        "operationId": "getOrderById",
+        "produces": [
+          "application/xml",
+          "application/json"
+        ],
+        "parameters": [
+          {
+            "name": "orderId",
+            "in": "path",
+            "description": "ID of pet that needs to be fetched",
+            "required": true,
+            "type": "integer",
+            "maximum": 10.0,
+            "minimum": 1.0,
+            "format": "int64"
+          }
+        ],
+        "responses": {
+          "200": {
+            "description": "successful operation",
+            "schema": {
+              "$ref": "#/definitions/Order"
+            }
+          },
+          "400": {
+            "description": "Invalid ID supplied"
+          },
+          "404": {
+            "description": "Order not found"
+          }
+        }
+      },
+      "delete": {
+        "tags": [
+          "store"
+        ],
+        "summary": "Delete purchase order by ID",
+        "description": "For valid response try integer IDs with positive integer value. Negative or non-integer values will generate API errors",
+        "operationId": "deleteOrder",
+        "produces": [
+          "application/xml",
+          "application/json"
+        ],
+        "parameters": [
+          {
+            "name": "orderId",
+            "in": "path",
+            "description": "ID of the order that needs to be deleted",
+            "required": true,
+            "type": "integer",
+            "minimum": 1.0,
+            "format": "int64"
+          }
+        ],
+        "responses": {
+          "400": {
+            "description": "Invalid ID supplied"
+          },
+          "404": {
+            "description": "Order not found"
+          }
+        }
+      }
+    },
+    "/user": {
+      "post": {
+        "tags": [
+          "user"
+        ],
+        "summary": "Create user",
+        "description": "This can only be done by the logged in user.",
+        "operationId": "createUser",
+        "produces": [
+          "application/xml",
+          "application/json"
+        ],
+        "parameters": [
+          {
+            "in": "body",
+            "name": "body",
+            "description": "Created user object",
+            "required": true,
+            "schema": {
+              "$ref": "#/definitions/User"
+            }
+          }
+        ],
+        "responses": {
+          "default": {
+            "description": "successful operation"
+          }
+        }
+      }
+    },
+    "/user/createWithArray": {
+      "post": {
+        "tags": [
+          "user"
+        ],
+        "summary": "Creates list of users with given input array",
+        "description": "",
+        "operationId": "createUsersWithArrayInput",
+        "produces": [
+          "application/xml",
+          "application/json"
+        ],
+        "parameters": [
+          {
+            "in": "body",
+            "name": "body",
+            "description": "List of user object",
+            "required": true,
+            "schema": {
+              "type": "array",
+              "items": {
+                "$ref": "#/definitions/User"
+              }
+            }
+          }
+        ],
+        "responses": {
+          "default": {
+            "description": "successful operation"
+          }
+        }
+      }
+    },
+    "/user/createWithList": {
+      "post": {
+        "tags": [
+          "user"
+        ],
+        "summary": "Creates list of users with given input array",
+        "description": "",
+        "operationId": "createUsersWithListInput",
+        "produces": [
+          "application/xml",
+          "application/json"
+        ],
+        "parameters": [
+          {
+            "in": "body",
+            "name": "body",
+            "description": "List of user object",
+            "required": true,
+            "schema": {
+              "type": "array",
+              "items": {
+                "$ref": "#/definitions/User"
+              }
+            }
+          }
+        ],
+        "responses": {
+          "default": {
+            "description": "successful operation"
+          }
+        }
+      }
+    },
+    "/user/login": {
+      "get": {
+        "tags": [
+          "user"
+        ],
+        "summary": "Logs user into the system",
+        "description": "",
+        "operationId": "loginUser",
+        "produces": [
+          "application/xml",
+          "application/json"
+        ],
+        "parameters": [
+          {
+            "name": "username",
+            "in": "query",
+            "description": "The user name for login",
+            "required": true,
+            "type": "string"
+          },
+          {
+            "name": "password",
+            "in": "query",
+            "description": "The password for login in clear text",
+            "required": true,
+            "type": "string"
+          }
+        ],
+        "responses": {
+          "200": {
+            "description": "successful operation",
+            "schema": {
+              "type": "string"
+            },
+            "headers": {
+              "X-Rate-Limit": {
+                "type": "integer",
+                "format": "int32",
+                "description": "calls per hour allowed by the user"
+              },
+              "X-Expires-After": {
+                "type": "string",
+                "format": "date-time",
+                "description": "date in UTC when token expires"
+              }
+            }
+          },
+          "400": {
+            "description": "Invalid username/password supplied"
+          }
+        }
+      }
+    },
+    "/user/logout": {
+      "get": {
+        "tags": [
+          "user"
+        ],
+        "summary": "Logs out current logged in user session",
+        "description": "",
+        "operationId": "logoutUser",
+        "produces": [
+          "application/xml",
+          "application/json"
+        ],
+        "parameters": [],
+        "responses": {
+          "default": {
+            "description": "successful operation"
+          }
+        }
+      }
+    },
+    "/user/{username}": {
+      "get": {
+        "tags": [
+          "user"
+        ],
+        "summary": "Get user by user name",
+        "description": "",
+        "operationId": "getUserByName",
+        "produces": [
+          "application/xml",
+          "application/json"
+        ],
+        "parameters": [
+          {
+            "name": "username",
+            "in": "path",
+            "description": "The name that needs to be fetched. Use user1 for testing. ",
+            "required": true,
+            "type": "string"
+          }
+        ],
+        "responses": {
+          "200": {
+            "description": "successful operation",
+            "schema": {
+              "$ref": "#/definitions/User"
+            }
+          },
+          "400": {
+            "description": "Invalid username supplied"
+          },
+          "404": {
+            "description": "User not found"
+          }
+        }
+      },
+      "put": {
+        "tags": [
+          "user"
+        ],
+        "summary": "Updated user",
+        "description": "This can only be done by the logged in user.",
+        "operationId": "updateUser",
+        "produces": [
+          "application/xml",
+          "application/json"
+        ],
+        "parameters": [
+          {
+            "name": "username",
+            "in": "path",
+            "description": "name that need to be updated",
+            "required": true,
+            "type": "string"
+          },
+          {
+            "in": "body",
+            "name": "body",
+            "description": "Updated user object",
+            "required": true,
+            "schema": {
+              "$ref": "#/definitions/User"
+            }
+          }
+        ],
+        "responses": {
+          "400": {
+            "description": "Invalid user supplied"
+          },
+          "404": {
+            "description": "User not found"
+          }
+        }
+      },
+      "delete": {
+        "tags": [
+          "user"
+        ],
+        "summary": "Delete user",
+        "description": "This can only be done by the logged in user.",
+        "operationId": "deleteUser",
+        "produces": [
+          "application/xml",
+          "application/json"
+        ],
+        "parameters": [
+          {
+            "name": "username",
+            "in": "path",
+            "description": "The name that needs to be deleted",
+            "required": true,
+            "type": "string"
+          }
+        ],
+        "responses": {
+          "400": {
+            "description": "Invalid username supplied"
+          },
+          "404": {
+            "description": "User not found"
+          }
+        }
+      }
+    }
+  },
+  "securityDefinitions": {
+    "petstore_auth": {
+      "type": "oauth2",
+      "authorizationUrl": "http://petstore.swagger.io/oauth/dialog",
+      "flow": "implicit",
+      "scopes": {
+        "write:pets": "modify pets in your account",
+        "read:pets": "read your pets"
+      }
+    },
+    "api_key": {
+      "type": "apiKey",
+      "name": "api_key",
+      "in": "header"
+    }
+  },
+  "definitions": {
+    "Order": {
+      "type": "object",
+      "properties": {
+        "id": {
+          "type": "integer",
+          "format": "int64"
+        },
+        "petId": {
+          "type": "integer",
+          "format": "int64"
+        },
+        "quantity": {
+          "type": "integer",
+          "format": "int32"
+        },
+        "shipDate": {
+          "type": "string",
+          "format": "date-time"
+        },
+        "status": {
+          "type": "string",
+          "description": "Order Status",
+          "enum": [
+            "placed",
+            "approved",
+            "delivered"
+          ]
+        },
+        "complete": {
+          "type": "boolean",
+          "default": false
+        }
+      },
+      "xml": {
+        "name": "Order"
+      }
+    },
+    "Category": {
+      "type": "object",
+      "properties": {
+        "id": {
+          "type": "integer",
+          "format": "int64"
+        },
+        "name": {
+          "type": "string"
+        }
+      },
+      "xml": {
+        "name": "Category"
+      }
+    },
+    "User": {
+      "type": "object",
+      "properties": {
+        "id": {
+          "type": "integer",
+          "format": "int64"
+        },
+        "username": {
+          "type": "string"
+        },
+        "firstName": {
+          "type": "string"
+        },
+        "lastName": {
+          "type": "string"
+        },
+        "email": {
+          "type": "string"
+        },
+        "password": {
+          "type": "string"
+        },
+        "phone": {
+          "type": "string"
+        },
+        "userStatus": {
+          "type": "integer",
+          "format": "int32",
+          "description": "User Status"
+        }
+      },
+      "xml": {
+        "name": "User"
+      }
+    },
+    "Tag": {
+      "type": "object",
+      "properties": {
+        "id": {
+          "type": "integer",
+          "format": "int64"
+        },
+        "name": {
+          "type": "string"
+        }
+      },
+      "xml": {
+        "name": "Tag"
+      }
+    },
+    "Pet": {
+      "type": "object",
+      "required": [
+        "name",
+        "photoUrls"
+      ],
+      "properties": {
+        "id": {
+          "type": "integer",
+          "format": "int64"
+        },
+        "category": {
+          "$ref": "#/definitions/Category"
+        },
+        "name": {
+          "type": "string",
+          "example": "doggie"
+        },
+        "photoUrls": {
+          "type": "array",
+          "xml": {
+            "name": "photoUrl",
+            "wrapped": true
+          },
+          "items": {
+            "type": "string"
+          }
+        },
+        "tags": {
+          "type": "array",
+          "xml": {
+            "name": "tag",
+            "wrapped": true
+          },
+          "items": {
+            "$ref": "#/definitions/Tag"
+          }
+        },
+        "status": {
+          "type": "string",
+          "description": "pet status in the store",
+          "enum": [
+            "available",
+            "pending",
+            "sold"
+          ]
+        }
+      },
+      "xml": {
+        "name": "Pet"
+      }
+    },
+    "ApiResponse": {
+      "type": "object",
+      "properties": {
+        "code": {
+          "type": "integer",
+          "format": "int32"
+        },
+        "type": {
+          "type": "string"
+        },
+        "message": {
+          "type": "string"
+        }
+      }
+    }
+  },
+  "externalDocs": {
+    "description": "Find out more about Swagger",
+    "url": "http://swagger.io"
+  },
+  "x-samples-languages": "some invalid value"
+}