diff --git a/frontend/app_constants/HTTP_STATUS.js b/frontend/app_constants/HTTP_STATUS.js
index 5d5ce0532e..e891bc0e42 100644
--- a/frontend/app_constants/HTTP_STATUS.js
+++ b/frontend/app_constants/HTTP_STATUS.js
@@ -1,3 +1,4 @@
 export default {
+  INTERNAL_ERROR: /^50[0-5]$/,
   UNAUTHENTICATED: 401,
 };
diff --git a/frontend/redux/middlewares/redirect/index.js b/frontend/redux/middlewares/redirect/index.js
new file mode 100644
index 0000000000..7e620dcd58
--- /dev/null
+++ b/frontend/redux/middlewares/redirect/index.js
@@ -0,0 +1,24 @@
+/* eslint-disable no-unused-vars */
+import { get } from 'lodash';
+import { push } from 'react-router-redux';
+
+import APP_CONSTANTS from 'app_constants';
+
+const { HTTP_STATUS, PATHS } = APP_CONSTANTS;
+
+const redirectMiddleware = store => next => (action) => {
+  const { type, payload } = action;
+
+  if (type.endsWith('FAILURE')) {
+    const httpStatus = get(payload, 'errors.http_status');
+
+    if (HTTP_STATUS.INTERNAL_ERROR.test(httpStatus)) {
+      store.dispatch(push(PATHS.KOLIDE_500));
+    }
+  }
+
+  return next(action);
+};
+
+export default redirectMiddleware;
+
diff --git a/frontend/redux/middlewares/redirect/redirect.tests.js b/frontend/redux/middlewares/redirect/redirect.tests.js
new file mode 100644
index 0000000000..8a6148aac4
--- /dev/null
+++ b/frontend/redux/middlewares/redirect/redirect.tests.js
@@ -0,0 +1,34 @@
+import expect from 'expect';
+
+import { reduxMockStore } from 'test/helpers';
+
+const errorAction = {
+  type: 'users_LOAD_FAILURE',
+  payload: {
+    errors: {
+      http_status: 500,
+      base: 'Something went wrong',
+    },
+  },
+};
+const errorActionThunk = (dispatch) => {
+  dispatch(errorAction);
+
+  return Promise.reject();
+};
+
+describe('redirect - middleware', () => {
+  it('redirect to /500 when a 500 error message is dispatched', () => {
+    const mockStore = reduxMockStore();
+    const expectedRedirectAction = {
+      type: '@@router/CALL_HISTORY_METHOD',
+      payload: {
+        args: ['/500'],
+        method: 'push',
+      },
+    };
+
+    mockStore.dispatch(errorActionThunk);
+    expect(mockStore.getActions()).toInclude(expectedRedirectAction);
+  });
+});
diff --git a/frontend/redux/store.js b/frontend/redux/store.js
index ed9a1f3c30..766b5fa145 100644
--- a/frontend/redux/store.js
+++ b/frontend/redux/store.js
@@ -5,6 +5,7 @@ import { routerMiddleware } from 'react-router-redux';
 import thunkMiddleware from 'redux-thunk';
 
 import authMiddleware from './middlewares/auth';
+import redirectMiddleware from './middlewares/redirect';
 import reducers from './reducers';
 
 const initialState = {};
@@ -13,6 +14,7 @@ const appliedMiddleware = applyMiddleware(
   thunkMiddleware,
   routerMiddleware(browserHistory),
   authMiddleware,
+  redirectMiddleware,
   loadingBarMiddleware({
     promiseTypeSuffixes: ['REQUEST', 'SUCCESS', 'FAILURE'],
   }),
diff --git a/frontend/router/paths.js b/frontend/router/paths.js
index b5d8f7e875..9623cf7210 100644
--- a/frontend/router/paths.js
+++ b/frontend/router/paths.js
@@ -7,6 +7,7 @@ export default {
   },
   FORGOT_PASSWORD: '/login/forgot',
   HOME: '/',
+  KOLIDE_500: '/500',
   LOGIN: '/login',
   LOGOUT: '/logout',
   MANAGE_HOSTS: '/hosts/manage',
diff --git a/frontend/test/helpers.jsx b/frontend/test/helpers.jsx
index ec6ef2b4cd..db71f8e5c4 100644
--- a/frontend/test/helpers.jsx
+++ b/frontend/test/helpers.jsx
@@ -6,13 +6,14 @@ import { Provider } from 'react-redux';
 import thunk from 'redux-thunk';
 
 import authMiddleware from 'redux/middlewares/auth';
+import redirectMiddleware from 'redux/middlewares/redirect';
 
 export const fillInFormInput = (inputComponent, value) => {
   return inputComponent.simulate('change', { target: { value } });
 };
 
 export const reduxMockStore = (store = {}) => {
-  const middlewares = [thunk, authMiddleware];
+  const middlewares = [thunk, authMiddleware, redirectMiddleware];
   const mockStore = configureStore(middlewares);
 
   return mockStore(store);