diff --git a/background.html b/background.html
index 13e3ddf9..fa3edd17 100644
--- a/background.html
+++ b/background.html
@@ -143,20 +143,25 @@
     <div class='container'>
       <div class='message-container'></div>
       <div class='info'>
+        {{ #hasRetry }}
+          <h3 class='hasRetry clearfix'>
+            <button class='retry'>Resend</button>
+            <span>Failed to send to some recipients.</span>
+          </h3>
+        {{ /hasRetry }}
         <table>
           <tr><td class='label'>Sent</td><td> {{ sent_at }}</td></tr>
           <tr><td class='label'>Received</td><td> {{ received_at }}</td></tr>
-          <tr>
-            <td class='tofrom label'>{{ tofrom }}</td>
-            <td> <div class='contacts'></div> </td>
-          </tr>
           {{ #errors }}
             <tr>
               <td class='label'>Error</td>
               <td> <span class='error-message'>{{message}}</span> </td>
             </tr>
           {{ /errors }}
+            <tr> <td class='tofrom label'>{{tofrom}}</td> </tr>
         </table>
+        <div class='contacts'>
+        </div>
       </div>
     </div>
   </script>
@@ -243,20 +248,17 @@
   </script>
   <script type='text/x-tmpl-mustache' id='contact-detail'>
       <div>
+        {{ #errors }}
+            <span class='error-icon'>
+              <span class='error-message'>{{message}}</span>
+            </span>
+        {{ /errors }}
         {{> avatar }}
-        <span class='name'>{{ name }}</span>
+        <span class='name'>{{ name }}
         {{ #conflict }}
             <button class='conflict'><span>Verify</span></button>
         {{ /conflict }}
-        {{ #retry }}
-          <button class='retry'><span>Retry</span></button>
-          <span class='error-message'>{{message}}</span>
-        {{ /retry }}
-        {{ #errors }}
-            <div>
-              <span class='error-message'>{{message}}</span>
-            </div>
-        {{ /errors }}
+        </span>
       </div>
   </script>
   <script type='text/x-tmpl-mustache' id='key-conflict-dialogue'>
diff --git a/js/views/message_detail_view.js b/js/views/message_detail_view.js
index 20ea6e29..2eeea9bc 100644
--- a/js/views/message_detail_view.js
+++ b/js/views/message_detail_view.js
@@ -10,33 +10,22 @@
         templateName: 'contact-detail',
         initialize: function(options) {
             this.conflict = options.conflict;
-            this.retry = _.find(options.errors, function(e) {
-                return (e.name === 'OutgoingMessageError' ||
-                        e.name === 'SendMessageNetworkError');
-            });
             this.errors = _.reject(options.errors, function(e) {
                 return (e.name === 'IncomingIdentityKeyError' ||
-                        e.name === 'OutgoingIdentityKeyError' ||
-                        e.name === 'OutgoingMessageError' ||
-                        e.name === 'SendMessageNetworkError');
+                        e.name === 'OutgoingIdentityKeyError');
             });
         },
         events: {
-            'click .conflict': 'triggerConflict',
-            'click .retry': 'triggerRetry'
+            'click .conflict': 'triggerConflict'
         },
         triggerConflict: function() {
             this.$el.trigger('conflict', {conflict: this.conflict});
         },
-        triggerRetry: function() {
-            this.$el.trigger('retry', {error: this.retry});
-        },
         render_attributes: function() {
             return {
                 name     : this.model.getTitle(),
                 avatar   : this.model.getAvatar(),
                 conflict : this.conflict,
-                retry    : this.retry,
                 errors   : this.errors
             };
         }
@@ -54,7 +43,7 @@
         events: {
             'click .back': 'goBack',
             'conflict': 'conflictDialogue',
-            'retry': 'retryMessage',
+            'click .retry': 'retryMessage',
         },
         goBack: function() {
             this.trigger('back');
@@ -93,30 +82,43 @@
                 this.render();
             });
         },
-        retryMessage: function(e, data) {
-            this.model.resend(data.error.number);
+        retryMessage: function() {
+            var retrys = _.filter(this.model.get('errors'), function(e) {
+                return (e.name === 'OutgoingMessageError' ||
+                        e.name === 'SendMessageNetworkError');
+            });
+            _.map(retrys, 'number').forEach(function(number) {
+                this.model.resend(number);
+            }.bind(this));
         },
         renderContact: function(contact) {
+            var conflict = this.model.getKeyConflict(contact.id);
             var v = new ContactView({
                 model: contact,
-                conflict: this.model.getKeyConflict(contact.id),
+                conflict: conflict,
                 errors: this.errors[contact.id]
-            }).render().$el.appendTo(this.$('.contacts'));
+            }).render();
+            this.$('.contacts').append(v.el);
         },
         render: function() {
             this.errors = _.groupBy(this.model.get('errors'), 'number');
+            var hasRetry = _.find(this.model.get('errors'), function(e) {
+                return (e.name === 'OutgoingMessageError' ||
+                        e.name === 'SendMessageNetworkError');
+            });
             this.$el.html(Mustache.render(this.template, {
                 sent_at     : moment(this.model.get('sent_at')).toString(),
                 received_at : moment(this.model.get('received_at')).toString(),
                 tofrom      : this.model.isIncoming() ? 'From' : 'To',
-                errors      : this.errors['undefined']
+                errors      : this.errors['undefined'],
+                hasRetry    : hasRetry
             }));
             this.view.render().$el.prependTo(this.$('.message-container'));
 
             if (this.model.isOutgoing()) {
                 this.conversation.contactCollection.reject(function(c) {
                     return c.id === textsecure.storage.user.getNumber();
-                }).each(this.renderContact.bind(this));
+                }).forEach(this.renderContact.bind(this));
             } else {
                 this.renderContact(
                     this.conversation.contactCollection.get(this.model.get('source'))
diff --git a/stylesheets/_conversation.scss b/stylesheets/_conversation.scss
index 58ba0515..4e3dda47 100644
--- a/stylesheets/_conversation.scss
+++ b/stylesheets/_conversation.scss
@@ -54,39 +54,96 @@
     padding: 1em;
 
     .label {
-      text-align: right;
       font-weight: bold;
       padding-right: 1em;
       vertical-align: top;
     }
+
+    button {
+      border: none;
+      border-radius: 5px;
+      color: white;
+      padding: 0.5em;
+      font-weight: bold;
+      background: $blue;
+
+      span {
+        vertical-align: middle;
+      }
+
+      &:before {
+        content: '';
+        display: inline-block;
+        vertical-align: middle;
+        width: 18px;
+        height: 18px;
+        background: url('/images/refresh.png') no-repeat center center;
+        background-size: 100%;
+      }
+    }
   }
 
-  .contact-detail button {
-    border: none;
-    border-radius: 5px;
-    color: white;
-    padding: 0.5em;
-    font-weight: bold;
-    background: $blue;
+  .contact-detail {
+    margin-bottom: 5px;
+    padding: 0 36px;
+  }
+
+  h3 {
+    font-size: 1em;
+    padding: 5px;
+
+    button {
+      float: right;
+    }
+  }
+
+  .error-icon {
+    display: inline-block;
+    width: 18px;
+    height: 18px;
+    background: url('/images/error_red.png') no-repeat center center;
+    vertical-align: middle;
+    position: relative;
+    margin: 9px;
+    float: right;
+
+    .error-message {
+      display: none;
+      position: absolute;
+      background: black;
+      color: white;
+      border-radius: 10px;
+      padding: 0.5em;
+      font-weight: normal;
+      bottom: calc(100% + 16px);
+      left: 50%;
+      margin-left: -130px;
+      width: 180px;
+      z-index: 10;
+
+      &:before {
+        left: -10px;
+        display: block;
+        content: '';
+        position: absolute;
+        bottom: -23px;
+        left: calc(50% - 6px + 40px);
+        border: 6px solid transparent;
+        border-top: 18px solid #000000;
+      }
+    }
+
+    &:hover .error-message { display: block; }
+  }
+
+  button.conflict {
+    float: right;
+    background: #d00;
 
     span {
-      vertical-align: middle;
       padding-left: 5px;
     }
 
-    &:before {
-      content: '';
-      display: inline-block;
-      vertical-align: middle;
-      width: 18px;
-      height: 18px;
-      background: url('/images/refresh.png') no-repeat center center;
-      background-size: 100%;
-    }
-  }
-  .conflict {
-    background: #d00;
-
     &:before {
       background: url('/images/error.png') no-repeat center center;
     }
diff --git a/stylesheets/manifest.css b/stylesheets/manifest.css
index 8234fc8a..b7b0d4b4 100644
--- a/stylesheets/manifest.css
+++ b/stylesheets/manifest.css
@@ -546,31 +546,73 @@ input.search {
   .message-detail .info {
     padding: 1em; }
     .message-detail .info .label {
-      text-align: right;
       font-weight: bold;
       padding-right: 1em;
       vertical-align: top; }
-  .message-detail .contact-detail button {
-    border: none;
-    border-radius: 5px;
-    color: white;
-    padding: 0.5em;
-    font-weight: bold;
-    background: #2090ea; }
-    .message-detail .contact-detail button span {
-      vertical-align: middle;
-      padding-left: 5px; }
-    .message-detail .contact-detail button:before {
-      content: '';
-      display: inline-block;
-      vertical-align: middle;
-      width: 18px;
-      height: 18px;
-      background: url("/images/refresh.png") no-repeat center center;
-      background-size: 100%; }
-  .message-detail .conflict {
+    .message-detail .info button {
+      border: none;
+      border-radius: 5px;
+      color: white;
+      padding: 0.5em;
+      font-weight: bold;
+      background: #2090ea; }
+      .message-detail .info button span {
+        vertical-align: middle; }
+      .message-detail .info button:before {
+        content: '';
+        display: inline-block;
+        vertical-align: middle;
+        width: 18px;
+        height: 18px;
+        background: url("/images/refresh.png") no-repeat center center;
+        background-size: 100%; }
+  .message-detail .contact-detail {
+    margin-bottom: 5px;
+    padding: 0 36px; }
+  .message-detail h3 {
+    font-size: 1em;
+    padding: 5px; }
+    .message-detail h3 button {
+      float: right; }
+  .message-detail .error-icon {
+    display: inline-block;
+    width: 18px;
+    height: 18px;
+    background: url("/images/error_red.png") no-repeat center center;
+    vertical-align: middle;
+    position: relative;
+    margin: 9px;
+    float: right; }
+    .message-detail .error-icon .error-message {
+      display: none;
+      position: absolute;
+      background: black;
+      color: white;
+      border-radius: 10px;
+      padding: 0.5em;
+      font-weight: normal;
+      bottom: calc(100% + 16px);
+      left: 50%;
+      margin-left: -130px;
+      width: 180px;
+      z-index: 10; }
+      .message-detail .error-icon .error-message:before {
+        left: -10px;
+        display: block;
+        content: '';
+        position: absolute;
+        bottom: -23px;
+        left: calc(50% - 6px + 40px);
+        border: 6px solid transparent;
+        border-top: 18px solid #000000; }
+    .message-detail .error-icon:hover .error-message {
+      display: block; }
+  .message-detail button.conflict {
+    float: right;
     background: #d00; }
-    .message-detail .conflict:before {
+    .message-detail button.conflict span {
+      padding-left: 5px; }
+    .message-detail button.conflict:before {
       background: url("/images/error.png") no-repeat center center; }
 
 .group-update {