diff --git a/src/Setup.react.js b/src/Setup.react.js
index c082585886..f97495f33d 100644
--- a/src/Setup.react.js
+++ b/src/Setup.react.js
@@ -84,8 +84,8 @@ var Setup = React.createClass({
         <div className="desc">
           <div className="content">
             <h4>Installation Cancelled</h4>
-            <h1>Couldn&#39;t Install VirtualBox</h1>
-            <p>Kitematic did not receive the administrative privileges required to install VirtualBox &amp; Docker.</p>
+            <h1>Couldn&#39;t Install</h1>
+            <p>Kitematic didn&#39;t receive the administrative privileges required to install or upgrade VirtualBox &amp; Docker.</p>
             <p>Please retry or download &amp; install VirutalBox manually from the <a onClick={this.handleOpenWebsite}>official Oracle website</a>.</p>
             <button className="btn btn-action" onClick={this.handleRetry}>Retry</button>
           </div>
diff --git a/src/SetupStore.js b/src/SetupStore.js
index 2f8deee106..8160f9bbc8 100644
--- a/src/SetupStore.js
+++ b/src/SetupStore.js
@@ -30,8 +30,8 @@ var _steps = [{
   }
 }, {
   name: 'install',
-  title: 'Installing Docker & VirtualBox',
-  message: 'VirtualBox is being installed in the background. We may need you to type in your password to continue.',
+  title: 'Installing VirtualBox & Docker',
+  message: 'VirtualBox & Docker are being installed or upgraded in the background. We may need you to type in your password to continue.',
   totalPercent: 5,
   percent: 0,
   seconds: 5,
@@ -146,7 +146,7 @@ var SetupStore = assign(Object.create(EventEmitter.prototype), {
     required.download = !virtualBox.installed() && (!fs.existsSync(vboxfile) || setupUtil.checksum(vboxfile) !== packagejson['virtualbox-checksum']);
     required.install = !virtualBox.installed() || setupUtil.needsBinaryFix() || setupUtil.compareVersions(yield virtualBox.version(), packagejson['virtualbox-required-version']) < 0;
     required.init = !(yield boot2docker.exists()) || !isoversion || setupUtil.compareVersions(isoversion, boot2docker.version()) < 0;
-    required.start = required.init || (yield boot2docker.status()) !== 'running';
+    required.start = required.install || required.init || (yield boot2docker.status()) !== 'running';
 
     var exists = yield boot2docker.exists();
     if (exists) {
diff --git a/src/SetupUtil.js b/src/SetupUtil.js
index a2597bffd4..381ec30119 100644
--- a/src/SetupUtil.js
+++ b/src/SetupUtil.js
@@ -38,7 +38,7 @@ var SetupUtil = {
     return `https://github.com/kitematic/virtualbox/releases/download/${packagejson['virtualbox-version']}/${packagejson['virtualbox-filename']}`;
   },
   macSudoCmd: function (cmd) {
-    return `${util.escapePath(path.join(util.resourceDir(), 'macsudo'))} -p "Kitematic requires administrative privileges to install VirtualBox." sh -c \"${cmd}\"`;
+    return `${util.escapePath(path.join(util.resourceDir(), 'macsudo'))} -p "Kitematic requires administrative privileges to install." sh -c \"${cmd}\"`;
   },
   simulateProgress: function (estimateSeconds, progress) {
     var times = _.range(0, estimateSeconds * 1000, 200);