diff --git a/__tests__/SetupStore-test.js b/__tests__/SetupStore-test.js
index e0a393bfb1..de3c2d4dd1 100644
--- a/__tests__/SetupStore-test.js
+++ b/__tests__/SetupStore-test.js
@@ -61,7 +61,9 @@ describe('SetupStore', function () {
 
   describe('init step', function () {
     virtualBox.vmdestroy.mockReturnValue(Promise.resolve());
-    pit('inintializes the boot2docker vm if it does not exist', function () {
+    pit('inintializes the machine vm if it does not exist', function () {
+      util.home.mockReturnValue('home');
+      machine.name.mockReturnValue('name');
       machine.exists.mockReturnValue(Promise.resolve(false));
       machine.create.mockReturnValue(Promise.resolve());
       return setupStore.steps().init.run().then(() => {
diff --git a/package.json b/package.json
index d3214731de..352aa09b10 100644
--- a/package.json
+++ b/package.json
@@ -1,6 +1,6 @@
 {
   "name": "Kitematic",
-  "version": "0.5.2",
+  "version": "0.5.3",
   "author": "Kitematic",
   "description": "Simple Docker Container management for Mac OS X.",
   "homepage": "https://kitematic.com/",
diff --git a/src/ContainerDetails.react.js b/src/ContainerDetails.react.js
index 1063adf9c3..f101b603ba 100644
--- a/src/ContainerDetails.react.js
+++ b/src/ContainerDetails.react.js
@@ -28,7 +28,7 @@ var ContainerDetail = React.createClass({
       <div className="details">
         <ContainerDetailsHeader container={this.props.container}/>
         <ContainerDetailsSubheader container={this.props.container} />
-        <Router.RouteHandler container={this.props.container}/>
+        <Router.RouteHandler container={this.props.container} error={this.props.error}/>
       </div>
     );
   }
diff --git a/src/ContainerHome.react.js b/src/ContainerHome.react.js
index 2d9a4f4091..45edefcf3d 100644
--- a/src/ContainerHome.react.js
+++ b/src/ContainerHome.react.js
@@ -8,7 +8,7 @@ var ContainerHomePreview = require('./ContainerHomePreview.react');
 var ContainerHomeLogs = require('./ContainerHomeLogs.react');
 var ContainerHomeFolders = require('./ContainerHomeFolders.react');
 var ContainerUtil = require('./ContainerUtil');
-var webPorts = require('./Util').webPorts;
+var util = require('./Util');
 
 var resizeWindow = function () {
   $('.left .wrapper').height(window.innerHeight - 240);
@@ -27,6 +27,9 @@ var ContainerHome = React.createClass({
   handleResize: function () {
     resizeWindow();
   },
+  handleErrorClick: function () {
+    util.exec(['open', 'https://github.com/kitematic/kitematic/issues/new']);
+  },
   componentWillReceiveProps: function () {
     this.init();
   },
@@ -52,7 +55,7 @@ var ContainerHome = React.createClass({
     this.setState({
       ports: ports,
       defaultPort: _.find(_.keys(ports), function (port) {
-        return webPorts.indexOf(port) !== -1;
+        return util.webPorts.indexOf(port) !== -1;
       }),
       progress: ContainerStore.progress(this.getParams().name),
       blocked: ContainerStore.blocked(this.getParams().name)
@@ -68,7 +71,14 @@ var ContainerHome = React.createClass({
   },
   render: function () {
     var body;
-    if (this.props.container && this.props.container.State.Downloading) {
+    if (this.props.error) {
+      body = (
+        <div className="details-progress">
+          <h3>There was a problem connecting to the Docker Engine.<br/>Either the VirtualBox VM was removed, is not responding or Docker is not running inside of it. Try restarting Kitematic. If the issue persists, please <a onClick={this.handleErrorClick}>file a ticket on our GitHub repo.</a></h3>
+          <Radial progress={100} error={true} thick={true} transparent={true}/>
+        </div>
+      );
+    } else if (this.props.container && this.props.container.State.Downloading) {
       if (this.state.progress) {
         body = (
           <div className="details-progress">
diff --git a/src/ContainerStore.js b/src/ContainerStore.js
index 25fdce97b3..1a07b76131 100644
--- a/src/ContainerStore.js
+++ b/src/ContainerStore.js
@@ -7,17 +7,20 @@ var docker = require('./Docker');
 var metrics = require('./Metrics');
 var registry = require('./Registry');
 var LogStore = require('./LogStore');
+var bugsnag = require('bugsnag-js');
 
 var _placeholders = {};
 var _containers = {};
 var _progress = {};
 var _muted = {};
 var _blocked = {};
+var _error = null;
 
 var ContainerStore = assign(Object.create(EventEmitter.prototype), {
   CLIENT_CONTAINER_EVENT: 'client_container_event',
   SERVER_CONTAINER_EVENT: 'server_container_event',
   SERVER_PROGRESS_EVENT: 'server_progress_event',
+  SERVER_ERROR_EVENT: 'server_error_event',
   _pullImage: function (repository, tag, callback, progressCallback, blockedCallback) {
     registry.layers(repository, tag, (err, layerSizes) => {
 
@@ -35,6 +38,10 @@ var ContainerStore = assign(Object.create(EventEmitter.prototype), {
 
         var totalBytes = layersToDownload.map(function (s) { return s.size; }).reduce(function (pv, sv) { return pv + sv; }, 0);
         docker.client().pull(repository + ':' + tag, (err, stream) => {
+          if (err) {
+            callback(err);
+            return;
+          }
           stream.setEncoding('utf8');
 
           var layerProgress = layersToDownload.reduce(function (r, layer) {
@@ -50,7 +57,7 @@ var ContainerStore = assign(Object.create(EventEmitter.prototype), {
             var data = JSON.parse(str);
             console.log(data);
 
-            if (data.status === 'Pulling dependent layers') {
+            if (data.status === 'Pulling dependent layers' || data.status.indexOf('already being pulled by another client') !== -1) {
               blockedCallback();
               return;
             }
@@ -153,7 +160,7 @@ var ContainerStore = assign(Object.create(EventEmitter.prototype), {
       }
     }
   },
-  _resumePulling: function () {
+  _resumePulling: function (callback) {
     var downloading = _.filter(_.values(this.containers()), function (container) {
       return container.State.Downloading;
     });
@@ -163,12 +170,20 @@ var ContainerStore = assign(Object.create(EventEmitter.prototype), {
     downloading.forEach(function (container) {
       _progress[container.Name] = 99;
       docker.client().pull(container.Config.Image, function (err, stream) {
+        if (err) {
+          callback(err);
+          return;
+        }
         stream.setEncoding('utf8');
         stream.on('data', function () {});
         stream.on('end', function () {
           delete _placeholders[container.Name];
           localStorage.setItem('store.placeholders', JSON.stringify(_placeholders));
-          self._createContainer(container.Name, {Image: container.Config.Image}, function () {
+          self._createContainer(container.Name, {Image: container.Config.Image}, err => {
+            if (err) {
+              callback(err);
+              return;
+            }
             self.emit(self.SERVER_PROGRESS_EVENT, container.Name);
             self.emit(self.CLIENT_CONTAINER_EVENT, container.Name);
           });
@@ -176,13 +191,17 @@ var ContainerStore = assign(Object.create(EventEmitter.prototype), {
       });
     });
   },
-  _startListeningToEvents: function () {
-    docker.client().getEvents(function (err, stream) {
+  _startListeningToEvents: function (callback) {
+    docker.client().getEvents((err, stream) => {
+      if (err) {
+        callback(err);
+        return;
+      }
       if (stream) {
         stream.setEncoding('utf8');
         stream.on('data', this._dockerEvent.bind(this));
       }
-    }.bind(this));
+    });
   },
   _dockerEvent: function (json) {
     var data = JSON.parse(json);
@@ -200,7 +219,7 @@ var ContainerStore = assign(Object.create(EventEmitter.prototype), {
         this.emit(this.SERVER_CONTAINER_EVENT, data.status);
       }
     } else {
-      this.fetchContainer(data.id, function (err) {
+      this.fetchContainer(data.id, err => {
         if (err) {
           return;
         }
@@ -209,13 +228,16 @@ var ContainerStore = assign(Object.create(EventEmitter.prototype), {
           return;
         }
         this.emit(this.SERVER_CONTAINER_EVENT, container ? container.Name : null, data.status);
-      }.bind(this));
+      });
     }
   },
   init: function (callback) {
     // TODO: Load cached data from db on loading
-    this.fetchAllContainers(function (err) {
+    this.fetchAllContainers(err => {
       if (err) {
+        _error = err;
+        this.emit(this.SERVER_ERROR_EVENT, err);
+        bugsnag.notify(err, 'Container Store failed to init', err);
         callback(err);
         return;
       } else {
@@ -227,12 +249,20 @@ var ContainerStore = assign(Object.create(EventEmitter.prototype), {
         localStorage.setItem('store.placeholders', JSON.stringify(_placeholders));
       }
       this.emit(this.CLIENT_CONTAINER_EVENT);
-      this._resumePulling();
-      this._startListeningToEvents();
-    }.bind(this));
+      this._resumePulling(err => {
+        _error = err;
+        this.emit(this.SERVER_ERROR_EVENT, err);
+        bugsnag.notify(err, 'Container Store failed to resume pulling', err);
+      });
+      this._startListeningToEvents(err => {
+        _error = err;
+        this.emit(this.SERVER_ERROR_EVENT, err);
+        bugsnag.notify(err, 'Container Store failed to listen to events', err);
+      });
+    });
   },
   fetchContainer: function (id, callback) {
-    docker.client().getContainer(id).inspect(function (err, container) {
+    docker.client().getContainer(id).inspect((err, container) => {
       if (err) {
         callback(err);
       } else {
@@ -245,11 +275,10 @@ var ContainerStore = assign(Object.create(EventEmitter.prototype), {
         _containers[container.Name] = container;
         callback(null, container);
       }
-    }.bind(this));
+    });
   },
   fetchAllContainers: function (callback) {
-    var self = this;
-    docker.client().listContainers({all: true}, function (err, containers) {
+    docker.client().listContainers({all: true}, (err, containers) => {
       if (err) {
         callback(err);
         return;
@@ -260,8 +289,8 @@ var ContainerStore = assign(Object.create(EventEmitter.prototype), {
           delete _containers[name];
         }
       });
-      async.each(containers, function (container, callback) {
-        self.fetchContainer(container.Id, function (err) {
+      async.each(containers, (container, callback) => {
+        this.fetchContainer(container.Id, function (err) {
           callback(err);
         });
       }, function (err) {
@@ -289,14 +318,28 @@ var ContainerStore = assign(Object.create(EventEmitter.prototype), {
 
     _muted[containerName] = true;
     _progress[containerName] = 0;
-    this._pullImage(repository, tag, () => {
+    this._pullImage(repository, tag, err => {
+      if (err) {
+        _error = err;
+        this.emit(this.SERVER_ERROR_EVENT, err);
+        bugsnag.notify(err, 'Container Store failed to create container', err);
+        return;
+      }
+      _error = null;
       _blocked[containerName] = false;
       if (!_placeholders[containerName]) {
         return;
       }
       delete _placeholders[containerName];
       localStorage.setItem('store.placeholders', JSON.stringify(_placeholders));
-      this._createContainer(containerName, {Image: imageName}, () => {
+      this._createContainer(containerName, {Image: imageName}, err => {
+        if (err) {
+          console.log(err);
+          _error = err;
+          this.emit(this.SERVER_ERROR_EVENT, err);
+          return;
+        }
+        _error = null;
         metrics.track('Container Finished Creating');
         delete _progress[containerName];
         _muted[containerName] = false;
@@ -321,10 +364,10 @@ var ContainerStore = assign(Object.create(EventEmitter.prototype), {
       LogStore.rename(name, data.name);
     }
     var fullData = assign(_containers[name], data);
-    this._createContainer(name, fullData, function (err) {
+    this._createContainer(name, fullData, function () {
       _muted[name] = false;
       this.emit(this.CLIENT_CONTAINER_EVENT, name);
-      callback(err);
+      callback();
     }.bind(this));
   },
   rename: function (name, newName, callback) {
@@ -417,6 +460,9 @@ var ContainerStore = assign(Object.create(EventEmitter.prototype), {
   },
   blocked: function (name) {
     return !!_blocked[name];
+  },
+  error: function () {
+    return _error;
   }
 });
 
diff --git a/src/Containers.react.js b/src/Containers.react.js
index eabe21e139..a3f935f4c8 100644
--- a/src/Containers.react.js
+++ b/src/Containers.react.js
@@ -20,11 +20,13 @@ var Containers = React.createClass({
       containers: ContainerStore.containers(),
       sorted: ContainerStore.sorted(),
       updateAvailable: false,
-      currentButtonLabel: ''
+      currentButtonLabel: '',
+      error: ContainerStore.error()
     };
   },
   componentDidMount: function () {
     this.update();
+    ContainerStore.on(ContainerStore.SERVER_ERROR_EVENT, this.updateError);
     ContainerStore.on(ContainerStore.SERVER_CONTAINER_EVENT, this.update);
     ContainerStore.on(ContainerStore.CLIENT_CONTAINER_EVENT, this.updateFromClient);
 
@@ -52,6 +54,11 @@ var Containers = React.createClass({
       this.transitionTo('containers');
     }
   },
+  updateError: function (err) {
+    this.setState({
+      error: err
+    });
+  },
   update: function (name, status) {
     this.setState({
       containers: ContainerStore.containers(),
@@ -175,7 +182,7 @@ var Containers = React.createClass({
               <div className="sidebar-buttons-padding"></div>
             </section>
           </div>
-          <Router.RouteHandler container={container}/>
+          <Router.RouteHandler container={container} error={this.state.error}/>
         </div>
       </div>
     );
diff --git a/src/ImageCard.react.js b/src/ImageCard.react.js
index 7c83fa73be..b132aec25f 100644
--- a/src/ImageCard.react.js
+++ b/src/ImageCard.react.js
@@ -23,10 +23,7 @@ var ImageCard = React.createClass({
   },
   handleClick: function (name) {
     metrics.track('Created Container');
-    ContainerStore.create(name, this.state.chosenTag, function (err) {
-      if (err) {
-        throw err;
-      }
+    ContainerStore.create(name, this.state.chosenTag, function () {
       $(document.body).find('.new-container-item').parent().fadeOut();
     }.bind(this));
   },
diff --git a/src/Main.js b/src/Main.js
index 5a443bcff8..0853f811f5 100644
--- a/src/Main.js
+++ b/src/Main.js
@@ -6,13 +6,13 @@ var fs = require('fs');
 var path = require('path');
 var docker = require('./Docker');
 var router = require('./Router');
-var machine = require('./DockerMachine');
 var ContainerStore = require('./ContainerStore');
 var SetupStore = require('./SetupStore');
 var metrics = require('./Metrics');
 var template = require('./MenuTemplate');
 var util = require('./Util');
 var Menu = remote.require('menu');
+var bugsnag = require('bugsnag-js');
 
 window.addEventListener('resize', function () {
   fs.writeFileSync(path.join(util.supportDir(), 'size'), JSON.stringify({
@@ -38,7 +38,6 @@ if (process.env.NODE_ENV === 'development') {
   head.appendChild(script);
 }
 
-var bugsnag = require('bugsnag-js');
 bugsnag.apiKey = settingsjson.bugsnag;
 bugsnag.autoNotify = true;
 bugsnag.releaseStage = process.env.NODE_ENV === 'development' ? 'development' : 'production';
@@ -81,18 +80,25 @@ setInterval(function () {
 }, 14400000);
 
 router.run(Handler => React.render(<Handler/>, document.body));
-SetupStore.run().then(machine.info).then(machine => {
+SetupStore.setup().then(machine => {
+  console.log('setup complete');
+  console.log(machine);
   docker.setup(machine.url, machine.name);
   Menu.setApplicationMenu(Menu.buildFromTemplate(template()));
+  ContainerStore.on(ContainerStore.SERVER_ERROR_EVENT, (err) => {
+    bugsnag.notify(err);
+  });
   ContainerStore.init(function (err) {
     if (err) {
+      console.log(err);
       bugsnag.notify(err);
     }
     router.transitionTo('containers');
   });
 }).catch(err => {
   metrics.track('Setup Failed', {
-    step: SetupStore.step(),
+    step: 'catch',
+    message: err.message
   });
   bugsnag.notify(err);
   console.log(err);
diff --git a/src/Radial.react.js b/src/Radial.react.js
index d54cac6b3b..cc826167cd 100644
--- a/src/Radial.react.js
+++ b/src/Radial.react.js
@@ -3,7 +3,7 @@ var React = require('react/addons');
 var Radial = React.createClass({
   render: function () {
     var percentage;
-    if ((this.props.progress !== null && this.props.progress !== undefined) && !this.props.spin) {
+    if ((this.props.progress !== null && this.props.progress !== undefined) && !this.props.spin && !this.props.error) {
       percentage = (
         <div className="percentage"></div>
       );
diff --git a/src/Setup.react.js b/src/Setup.react.js
index da7264785f..c684dffffa 100644
--- a/src/Setup.react.js
+++ b/src/Setup.react.js
@@ -6,13 +6,15 @@ var RetinaImage = require('react-retina-image');
 var Header = require('./Header.react');
 var Util = require('./Util');
 var metrics = require('./Metrics');
+var machine = require('./DockerMachine');
 
 var Setup = React.createClass({
   mixins: [ Router.Navigation ],
   getInitialState: function () {
     return {
       progress: 0,
-      name: ''
+      name: '',
+      retrying: false
     };
   },
   componentWillMount: function () {
@@ -28,10 +30,26 @@ var Setup = React.createClass({
     SetupStore.removeListener(SetupStore.STEP_EVENT, this.update);
     SetupStore.removeListener(SetupStore.ERROR_EVENT, this.update);
   },
-  handleRetry: function () {
-    metrics.track('Setup Retried');
+  handleCancelRetry: function () {
+    metrics.track('Setup Retried', {
+      from: 'cancel'
+    });
     SetupStore.retry();
   },
+  handleErrorRetry: function () {
+    this.setState({
+      retrying: true
+    });
+    metrics.track('Setup Retried', {
+      from: 'error'
+    });
+    machine.stop().finally(() => {
+      this.setState({
+        retrying: false
+      });
+      SetupStore.retry();
+    });
+  },
   handleOpenWebsite: function () {
     Util.exec(['open', 'https://www.virtualbox.org/wiki/Downloads']);
   },
@@ -110,21 +128,21 @@ var Setup = React.createClass({
             <h1>We&#39;re Sorry!</h1>
             <p>There seems to have been an unexpected error with Kitematic:</p>
             <p className="error">{this.state.error}<br />{this.state.error.message}</p>
+            <p><button className="btn btn-action" disabled={this.state.retrying} onClick={this.handleErrorRetry}>Retry Setup</button></p>
           </div>
         </div>
       </div>
     );
   },
   render: function () {
-    if (!SetupStore.step()) {
-      return false;
-    }
     if (this.state.cancelled) {
       return this.renderCancelled();
     } else if (this.state.error) {
       return this.renderError();
-    } else {
+    } else if (SetupStore.step()) {
       return this.renderStep();
+    } else {
+      return false;
     }
   }
 });
diff --git a/src/SetupStore.js b/src/SetupStore.js
index 11478e593d..b2b04cd7f6 100644
--- a/src/SetupStore.js
+++ b/src/SetupStore.js
@@ -10,6 +10,7 @@ var util = require('./Util');
 var assign = require('object-assign');
 var metrics = require('./Metrics');
 var bugsnag = require('bugsnag-js');
+var rimraf = require('rimraf');
 
 var _currentStep = null;
 var _error = null;
@@ -59,26 +60,25 @@ var _steps = [{
   message: 'To run Docker containers on your computer, Kitematic is starting a Linux virutal machine. This may take a minute...',
   totalPercent: 60,
   percent: 0,
-  seconds: 52,
+  seconds: 53,
   run: Promise.coroutine(function* (progressCallback) {
     setupUtil.simulateProgress(this.seconds, progressCallback);
     yield virtualBox.vmdestroy('kitematic-vm');
     var exists = yield machine.exists();
-    if (!exists) {
-      yield machine.create();
-      return;
-    } else if ((yield machine.state()) === 'Error') {
+    if (!exists || (yield machine.state()) === 'Error') {
       try {
         yield machine.rm();
-      } catch (err) {}
-      yield machine.create();
+        yield machine.create();
+      } catch (err) {
+        rimraf.sync(path.join(util.home(), '.docker', 'machine', 'machines', machine.name()));
+        yield machine.create();
+      }
       return;
     }
 
     var isoversion = machine.isoversion();
     var packagejson = util.packagejson();
     if (!isoversion || setupUtil.compareVersions(isoversion, packagejson['docker-version']) < 0) {
-      console.log('upgrading');
       yield machine.stop();
       yield machine.upgrade();
     }
@@ -113,15 +113,21 @@ var SetupStore = assign(Object.create(EventEmitter.prototype), {
   error: function () {
     return _error;
   },
+  setError: function (error) {
+    _error = error;
+    this.emit(this.ERROR_EVENT);
+  },
   cancelled: function () {
     return _cancelled;
   },
   retry: function () {
     _error = null;
     _cancelled = false;
-    _retryPromise.resolve();
+    if (_retryPromise) {
+      _retryPromise.resolve();
+    }
   },
-  wait: function () {
+  pause: function () {
     _retryPromise = Promise.defer();
     return _retryPromise.promise;
   },
@@ -141,7 +147,7 @@ var SetupStore = assign(Object.create(EventEmitter.prototype), {
     if (isoversion && setupUtil.compareVersions(isoversion, packagejson['docker-version']) < 0) {
       this.steps().init.seconds = 33;
     } else if (exists && (yield machine.state()) !== 'Error') {
-      this.steps().init.seconds = 13;
+      this.steps().init.seconds = 23;
     }
 
     _requiredSteps = _steps.filter(function (step) {
@@ -196,12 +202,29 @@ var SetupStore = assign(Object.create(EventEmitter.prototype), {
             _cancelled = true;
             this.emit(this.STEP_EVENT);
           }
-          yield this.wait();
+          yield this.pause();
         }
       }
     }
-    metrics.track('Finished Setup');
     _currentStep = null;
+    return yield machine.info();
+  }),
+  setup: Promise.coroutine(function * () {
+    while (true) {
+      var info = yield this.run();
+      if (!info.url) {
+        metrics.track('Setup Failed', {
+          step: 'done',
+          message: 'Machine URL not set'
+        });
+        bugsnag.notify('SetupError', 'Machine url was not set', machine);
+        SetupStore.setError('Could not reach the Docker Engine inside the VirtualBox VM');
+        yield this.pause();
+      } else {
+        metrics.track('Finished Setup');
+        return info;
+      }
+    }
   })
 });
 
diff --git a/src/Util.js b/src/Util.js
index 949ac410c5..baa565bfca 100644
--- a/src/Util.js
+++ b/src/Util.js
@@ -9,7 +9,7 @@ module.exports = {
     return new Promise((resolve, reject) => {
       exec(args, options, (stderr, stdout, code) => {
         if (code) {
-          reject(stderr);
+          reject(stderr || args.join(' ').replace(this.home(), '') + 'returned non zero exit code');
         }
         resolve(stdout);
       });
diff --git a/styles/right-panel.less b/styles/right-panel.less
index 3afe086760..2d5af45524 100644
--- a/styles/right-panel.less
+++ b/styles/right-panel.less
@@ -122,7 +122,7 @@
   .details-progress {
     margin: 20% auto 0;
     text-align: center;
-    width: 300px;
+    width: 400px;
     h2 {
       margin-bottom: 20px;
     }
diff --git a/util/reset b/util/reset
index 56eb096e45..8e97b804bf 100755
--- a/util/reset
+++ b/util/reset
@@ -8,4 +8,5 @@ pkill VBox
 rm -rf ~/Library/Application\ Support/Kitematic/
 rm -rf ~/.docker
 rm -rf ~/Library/VirtualBox/
+rm -rf ~/Kitematic
 $DIR/VirtualBox_Uninstall.tool