diff --git a/_locales/en/messages.json b/_locales/en/messages.json
index e52d15b23..61a5424c6 100644
--- a/_locales/en/messages.json
+++ b/_locales/en/messages.json
@@ -3,6 +3,10 @@
       "message": "Me",
       "description": "The label for yourself when shown in a group member list"
     },
+    "view": {
+      "message": "View",
+      "description": "Used as a label on a button allowing user to see more information"
+    },
     "youLeftTheGroup": {
       "message": "You left the group",
       "description": "Displayed when a user can't send a message because they have left the group"
@@ -105,9 +109,15 @@
         }
       }
     },
-    "retryDescription": {
-      "message": "You can retry sending this message to each of the failed recipients with these buttons:",
-      "description": "Shows on the message details view when it's a message error which can be retried."
+    "identityKeyErrorOnSend": {
+      "message": "Your safety number with $name$ has changed. This could either mean that someone is trying to intercept your communication or that $name$ has simply reinstalled Signal. You may wish to verify your saftey number with this contact.",
+      "description": "Shown when user clicks on a failed recipient in the message detail view after an identity key change",
+      "placeholders": {
+        "name": {
+          "content": "$1",
+          "example": "Bob"
+        }
+      }
     },
     "sendAnyway": {
       "message": "Send Anyway",
diff --git a/background.html b/background.html
index fa26a92ef..17bac7fbd 100644
--- a/background.html
+++ b/background.html
@@ -297,14 +297,6 @@
   <script type='text/x-tmpl-mustache' id='message-detail'>
     <div class='container'>
       <div class='message-container'></div>
-      {{ #allowRetry }}
-        <div class='retries'>
-          <div>{{ retryDescription }}</div>
-          {{ #retryTargets }}
-            <button class='retry gray' data-number='{{ number }}'>{{ title }}</button>
-          {{ /retryTargets }}
-        </div>
-      {{ /allowRetry }}
       <div class='info'>
         <table>
           {{ #errors }}
@@ -330,6 +322,20 @@
       </div>
     </div>
   </script>
+  <script type='text/x-tmpl-mustache' id='identity-key-send-error'>
+    <div class='container'>
+      <div class='explanation'>
+        {{ errorExplanation }}
+      </div>
+      <div class='safety-number'>
+        <button class='show-safety-number grey'>{{ showSafetyNumber }}</button>
+      </div>
+      <div class='actions'>
+        <button class='send-anyway grey'>{{ sendAnyway }}</button>
+        <button class='cancel grey'>{{ cancel }}</button>
+      </div>
+    </div>
+  </script>
   <script type='text/x-tmpl-mustache' id='group-member-list'>
     <div class='container'>
       {{ #summary }} <div class='summary'>{{ summary }}</div>{{ /summary }}
@@ -415,7 +421,15 @@
         <div class='contact-details'>
           {{ #errors }}
               <div class='error-icon-container'>
-                <span class='error-icon'></span>
+                {{ #showErrorButton }}
+                  <button class='error'>
+                    <span class='icon error'></span>
+                    {{ errorButtonLabel }}
+                  </button>
+                {{ /showErrorButton }}
+                {{ ^showErrorButton }}
+                  <span class='error-icon'></span>
+                {{ /showErrorButton }}
               </div>
           {{ /errors }}
           <span class='name' dir='auto'>{{ name }}</span>
@@ -680,8 +694,9 @@
   <script type='text/javascript' src='js/views/confirmation_dialog_view.js'></script>
   <script type='text/javascript' src='js/views/identicon_svg_view.js'></script>
   <script type='text/javascript' src='js/views/settings_view.js'></script>
-  <script type="text/javascript" src="js/views/install_view.js"></script>
-  <script type="text/javascript" src="js/views/banner_view.js"></script>
+  <script type='text/javascript' src='js/views/install_view.js'></script>
+  <script type='text/javascript' src='js/views/banner_view.js'></script>
+  <script type='text/javascript' src='js/views/identity_key_send_error_view.js'></script>
 
   <script type='text/javascript' src='js/wall_clock_listener.js'></script>
   <script type='text/javascript' src='js/rotate_signed_prekey_listener.js'></script>
diff --git a/js/models/conversations.js b/js/models/conversations.js
index 9d9e56ab3..ffa667d6f 100644
--- a/js/models/conversations.js
+++ b/js/models/conversations.js
@@ -202,6 +202,14 @@
             }.bind(this)));
         }
     },
+    setTrusted: function() {
+        if (!this.isPrivate()) {
+            throw new Error('You cannot set a group conversation as trusted. ' +
+                            'You must set individual contacts as trusted.');
+        }
+
+        return textsecure.storage.protocol.setApproval(this.id, true);
+    },
     isUntrusted: function() {
         if (this.isPrivate()) {
             return textsecure.storage.protocol.isUntrusted(this.id);
diff --git a/js/views/conversation_view.js b/js/views/conversation_view.js
index daad70db7..f25dc9416 100644
--- a/js/views/conversation_view.js
+++ b/js/views/conversation_view.js
@@ -202,6 +202,13 @@
             }.bind(this)));
         },
 
+
+        markAllAsApproved: function(untrusted) {
+            return Promise.all(untrusted.map(function(contact) {
+                return contact.setApproved();
+            }.bind(this)));
+        },
+
         openSafetyNumberScreens: function(unverified) {
             if (unverified.length === 1) {
                 this.showSafetyNumber(null, unverified.at(0));
@@ -620,7 +627,10 @@
         messageDetail: function(e, data) {
             var view = new Whisper.MessageDetailView({
                 model: data.message,
-                conversation: this.model
+                conversation: this.model,
+                // we pass these in to allow nested panels
+                listenBack: this.listenBack.bind(this),
+                resetPanel: this.resetPanel.bind(this)
             });
             this.listenBack(view);
             view.render();
@@ -749,10 +759,17 @@
             _.defaults(options, {force: false});
 
             this.model.getUntrusted().then(function(contacts) {
-                if (!contacts.length || options.force) {
+
+                if (!contacts.length) {
                     return this.sendMessage(e);
                 }
 
+                if (options.force) {
+                    return this.markAllAsApproved(contacts).then(function() {
+                        this.sendMessage(e);
+                    }.bind(this));
+                }
+
                 this.showSendConfirmationDialog(e, contacts);
             }.bind(this));
         },
diff --git a/js/views/identity_key_send_error_view.js b/js/views/identity_key_send_error_view.js
new file mode 100644
index 000000000..99c5d0666
--- /dev/null
+++ b/js/views/identity_key_send_error_view.js
@@ -0,0 +1,51 @@
+/*
+ * vim: ts=4:sw=4:expandtab
+ */
+(function () {
+    'use strict';
+    window.Whisper = window.Whisper || {};
+
+    Whisper.IdentityKeySendErrorPanelView = Whisper.View.extend({
+        className: 'identity-key-send-error panel',
+        templateName: 'identity-key-send-error',
+        initialize: function(options) {
+            this.listenBack = options.listenBack;
+            this.resetPanel = options.resetPanel;
+
+            this.wasUnverified = this.model.isUnverified();
+            this.listenTo(this.model, 'change', this.render);
+        },
+        events: {
+            'click .show-safety-number': 'showSafetyNumber',
+            'click .send-anyway': 'sendAnyway',
+            'click .cancel': 'cancel'
+        },
+        showSafetyNumber: function() {
+            var view = new Whisper.KeyVerificationPanelView({
+                model: this.model
+            });
+            this.listenBack(view);
+        },
+        sendAnyway: function() {
+            this.resetPanel();
+            this.trigger('send-anyway');
+        },
+        cancel: function() {
+            this.resetPanel();
+        },
+        render_attributes: function() {
+            var send = i18n('sendAnyway');
+            if (this.wasUnverified && !this.model.isUnverified()) {
+                send = i18n('resend');
+            }
+
+            var errorExplanation = i18n('identityKeyErrorOnSend', this.model.getTitle(), this.model.getTitle());
+            return {
+                errorExplanation : errorExplanation,
+                showSafetyNumber : i18n('showSafetyNumber'),
+                sendAnyway       : send,
+                cancel           : i18n('cancel')
+            };
+        }
+    });
+})();
diff --git a/js/views/message_detail_view.js b/js/views/message_detail_view.js
index b9de420da..fccc19f30 100644
--- a/js/views/message_detail_view.js
+++ b/js/views/message_detail_view.js
@@ -9,18 +9,68 @@
         className: 'contact-detail',
         templateName: 'contact-detail',
         initialize: function(options) {
-            this.errors = _.reject(options.errors, function(e) {
-                return (e.name === 'OutgoingIdentityKeyError' ||
-                        e.name === 'OutgoingMessageError' ||
-                        e.name === 'SendMessageNetworkError');
+            this.listenBack = options.listenBack;
+            this.resetPanel = options.resetPanel;
+            this.message = options.message;
+
+            var newIdentity = i18n('newIdentity');
+            this.errors = _.map(options.errors, function(error) {
+                if (error.name === 'OutgoingIdentityKeyError') {
+                    error.message = newIdentity;
+                }
+                return error;
+            });
+            this.outgoingKeyError = _.find(this.errors, function(error) {
+                return error.name === 'OutgoingIdentityKeyError';
             });
+        },
+        events: {
+            'click': 'onClick'
+        },
+        onClick: function() {
+            if (this.outgoingKeyError) {
+                var view = new Whisper.IdentityKeySendErrorPanelView({
+                    model: this.model,
+                    listenBack: this.listenBack,
+                    resetPanel: this.resetPanel
+                });
+
+                this.listenTo(view, 'send-anyway', this.onSendAnyway);
 
+                view.render();
+                this.listenBack(view);
+            }
+            // TODO: is there anything we might want to do here? Pop a confirmation dialog? Ideally it would always have error-specific help.
+        },
+        forceSend: function() {
+            this.model.updateVerified().then(function() {
+                if (this.model.isUnverified()) {
+                    return this.model.setVerifiedDefault();
+                }
+            }.bind(this)).then(function() {
+                return this.model.isUntrusted();
+            }.bind(this)).then(function(untrusted) {
+                if (untrusted) {
+                    return this.model.setTrusted();
+                }
+            }.bind(this)).then(function() {
+                this.message.resend(this.outgoingKeyError.number);
+            }.bind(this));
+        },
+        onSendAnyway: function() {
+            if (this.outgoingKeyError) {
+                this.forceSend();
+            }
         },
         render_attributes: function() {
+            var showButton = Boolean(this.outgoingKeyError);
+
             return {
-                name     : this.model.getTitle(),
-                avatar   : this.model.getAvatar(),
-                errors   : this.errors
+                name             : this.model.getTitle(),
+                avatar           : this.model.getAvatar(),
+                errors           : this.errors,
+                showErrorButton  : showButton,
+                errorButtonLabel : i18n('view')
             };
         }
     });
@@ -29,23 +79,15 @@
         className: 'message-detail panel',
         templateName: 'message-detail',
         initialize: function(options) {
+            this.listenBack = options.listenBack;
+            this.resetPanel = options.resetPanel;
+
             this.view = new Whisper.MessageView({model: this.model});
             this.view.render();
             this.conversation = options.conversation;
 
             this.listenTo(this.model, 'change', this.render);
         },
-        events: {
-            'click button.retry': 'onRetry'
-        },
-        onRetry: function(e) {
-            var number = _.find(e.target.attributes, function(attribute) {
-                return attribute.name === 'data-number';
-            });
-            if (number) {
-                this.model.resend(number.value);
-            }
-        },
         getContact: function(number) {
             var c = ConversationController.get(number);
             return {
@@ -53,15 +95,6 @@
                 title: c ? c.getTitle() : number
             };
         },
-        buildRetryTargetList: function() {
-            var targets = _.filter(this.model.get('errors'), function(e) {
-                return e.number && e.name === 'OutgoingIdentityKeyError';
-            });
-
-            return _.map(targets, function(e) {
-                return this.getContact(e.number);
-            }.bind(this));
-        },
         contacts: function() {
             if (this.model.isIncoming()) {
                 var number = this.model.get('source');
@@ -71,25 +104,25 @@
             }
         },
         renderContact: function(contact) {
-            var grouped = _.groupBy(this.model.get('errors'), 'number');
-
             var view = new ContactView({
                 model: contact,
-                errors: grouped[contact.id]
+                errors: this.grouped[contact.id],
+                listenBack: this.listenBack,
+                resetPanel: this.resetPanel,
+                message: this.model
             }).render();
             this.$('.contacts').append(view.el);
         },
         render: function() {
-            var retryTargets = this.buildRetryTargetList();
-            var allowRetry = retryTargets.length > 0;
+            var errorsWithoutNumber = _.reject(this.model.get('errors'), function(error) {
+                return Boolean(error.number);
+            });
 
             this.$el.html(Mustache.render(_.result(this, 'template', ''), {
                 sent_at         : moment(this.model.get('sent_at')).format('LLLL'),
                 received_at     : this.model.isIncoming() ? moment(this.model.get('received_at')).format('LLLL') : null,
                 tofrom          : this.model.isIncoming() ? i18n('from') : i18n('to'),
-                errors          : this.model.get('errors'),
-                allowRetry      : allowRetry,
-                retryTargets    : retryTargets,
+                errors          : errorsWithoutNumber,
                 title           : i18n('messageDetail'),
                 sent            : i18n('sent'),
                 received        : i18n('received'),
@@ -98,14 +131,21 @@
             }));
             this.view.$el.prependTo(this.$('.message-container'));
 
+            this.grouped = _.groupBy(this.model.get('errors'), 'number');
             if (this.model.isOutgoing()) {
-                this.conversation.contactCollection.reject(function(c) {
+                var contacts = this.conversation.contactCollection.reject(function(c) {
                     return c.isMe();
-                }).forEach(this.renderContact.bind(this));
+                });
+
+                _.sortBy(contacts, function(c) {
+                    var prefix = this.grouped[c.id] ? '0' : '1';
+                    // this prefix ensures that contacts with errors are listed first;
+                    //   otherwise it's alphabetical
+                    return prefix + c.getTitle();
+                }.bind(this)).forEach(this.renderContact.bind(this));
             } else {
-                this.renderContact(
-                    this.conversation.contactCollection.get(this.model.get('source'))
-                );
+                var c = this.conversation.contactCollection.get(this.model.get('source'));
+                this.renderContact(c);
             }
         }
     });
diff --git a/stylesheets/_conversation.scss b/stylesheets/_conversation.scss
index 96526899a..4bc0593ac 100644
--- a/stylesheets/_conversation.scss
+++ b/stylesheets/_conversation.scss
@@ -39,7 +39,7 @@
 
     .container {
       padding-top: 20px;
-      max-width: 950px;
+      max-width: 750px;
       margin: 0 auto;
       padding: 20px;
     }
@@ -77,10 +77,6 @@
 }
 
 .key-verification {
-  .container {
-    max-width: 750px;
-  }
-
   label {
     display: block;
     margin: 10px 0;
@@ -150,6 +146,24 @@
   }
 }
 
+.identity-key-send-error {
+  button {
+    margin-top: 0px;
+    margin-bottom: 0px;
+  }
+  .explanation {
+    margin-top: 20px;
+  }
+  .safety-number {
+    margin-top: 30px;
+    text-align: center;
+  }
+  .actions {
+    margin-top: 30px;
+    text-align: center;
+  }
+}
+
 .message-detail {
   background-color: #eee;
 
@@ -198,6 +212,20 @@
       float: right;
     }
 
+    button.error {
+      background-color: red;
+      color: white;
+
+      span.icon.error {
+        display: inline-block;
+        width: 1.25em;
+        height: 1.25em;
+        position: relative;
+        vertical-align: middle;
+        @include color-svg('/images/warning.svg', white);
+      }
+    }
+
     .error-message {
       margin: 6px 0 0;
       font-size: $font-size-small;
diff --git a/stylesheets/manifest.css b/stylesheets/manifest.css
index ca684fa11..45842eb7c 100644
--- a/stylesheets/manifest.css
+++ b/stylesheets/manifest.css
@@ -1057,7 +1057,7 @@ input.search {
     overflow-y: scroll; }
     .conversation .panel .container {
       padding-top: 20px;
-      max-width: 950px;
+      max-width: 750px;
       margin: 0 auto;
       padding: 20px; }
   .conversation .main.panel {
@@ -1083,8 +1083,6 @@ input.search {
 .discussion-container {
   background-color: #eee; }
 
-.key-verification .container {
-  max-width: 750px; }
 .key-verification label {
   display: block;
   margin: 10px 0;
@@ -1139,6 +1137,18 @@ input.search {
   padding: 10px;
   margin: 0; }
 
+.identity-key-send-error button {
+  margin-top: 0px;
+  margin-bottom: 0px; }
+.identity-key-send-error .explanation {
+  margin-top: 20px; }
+.identity-key-send-error .safety-number {
+  margin-top: 30px;
+  text-align: center; }
+.identity-key-send-error .actions {
+  margin-top: 30px;
+  text-align: center; }
+
 .message-detail {
   background-color: #eee; }
   .message-detail .message-container {
@@ -1168,6 +1178,18 @@ input.search {
     margin-bottom: 5px; }
     .message-detail .contacts .contact-detail .error-icon-container {
       float: right; }
+    .message-detail .contacts .contact-detail button.error {
+      background-color: red;
+      color: white; }
+      .message-detail .contacts .contact-detail button.error span.icon.error {
+        display: inline-block;
+        width: 1.25em;
+        height: 1.25em;
+        position: relative;
+        vertical-align: middle;
+        -webkit-mask: url("/images/warning.svg") no-repeat center;
+        -webkit-mask-size: 100%;
+        background-color: white; }
     .message-detail .contacts .contact-detail .error-message {
       margin: 6px 0 0;
       font-size: 0.92857em;
diff --git a/test/index.html b/test/index.html
index 17b9f724b..676bd198d 100644
--- a/test/index.html
+++ b/test/index.html
@@ -316,6 +316,20 @@
       </div>
     </div>
   </script>
+  <script type='text/x-tmpl-mustache' id='identity-key-send-error'>
+    <div class='container'>
+      <div class='explanation'>
+        {{ errorExplanation }}
+      </div>
+      <div class='safety-number'>
+        <button class='show-safety-number grey'>{{ showSafetyNumber }}</button>
+      </div>
+      <div class='actions'>
+        <button class='send-anyway grey'>{{ sendAnyway }}</button>
+        <button class='cancel grey'>{{ cancel }}</button>
+      </div>
+    </div>
+  </script>
   <script type='text/x-tmpl-mustache' id='group-member-list'>
     <div class='container'>
       {{ #summary }} <div class='summary'>{{ summary }}</div>{{ /summary }}
@@ -588,6 +602,7 @@
   <script type='text/javascript' src='../js/views/last_seen_indicator_view.js' data-cover></script>
   <script type='text/javascript' src='../js/views/scroll_down_button_view.js' data-cover></script>
   <script type='text/javascript' src='../js/views/banner_view.js' data-cover></script>
+  <script type="text/javascript" src='../js/views/identity_key_send_error_view.js' data-cover></script>
 
   <script type="text/javascript" src="views/whisper_view_test.js"></script>
   <script type="text/javascript" src="views/group_update_view_test.js"></script>