Version check gets how many versions behind you are, and shows judgemental faces on the dashboard

app/assets/javascripts/admin/models/version_check.js

@@ -8,8 +8,12 @@
 **/
 Discourse.VersionCheck = Discourse.Model.extend({
   upToDate: function() {
-    return this.get('latest_version') === this.get('installed_version');
-  }.property('latest_version', 'installed_version'),
+    return this.get('missing_versions_count') === 0;
+  }.property('missing_versions_count'),
+
+  behindByOneVersion: function() {
+    return this.get('missing_versions_count') === 1;
+  }.property('missing_versions_count'),
 
   gitLink: function() {
     return "https://github.com/discourse/discourse/tree/" + this.get('installed_sha');

app/assets/javascripts/admin/templates/dashboard.js.handlebars

@@ -14,9 +14,15 @@
       <p class="version-notes">
         {{i18n admin.dashboard.latest_version}}: <span class="version-number">{{ versionCheck.latest_version }}</span>
         {{#if versionCheck.upToDate }}
-          <i class='icon icon-ok update-to-date'></i> {{i18n admin.dashboard.up_to_date}}
+          <span class='icon update-to-date'>☻</span> {{i18n admin.dashboard.up_to_date}}
         {{else}}
-          <i {{bindAttr class=":icon :icon-warning-sign versionCheck.critical_updates:critical-updates-available:updates-available"}}></i>
+          <span {{bindAttr class=":icon versionCheck.critical_updates:critical-updates-available:updates-available"}}>
+            {{#if versionCheck.behindByOneVersion}}
+              ☺
+            {{else}}
+              ☹
+            {{/if}}
+          </span>
           <span class="critical-note">{{i18n admin.dashboard.critical_available}}</span>
           <span class="normal-note">{{i18n admin.dashboard.updates_available}}</span>
           {{i18n admin.dashboard.please_upgrade}}