diff --git a/js/models/conversations.js b/js/models/conversations.js
index 406f3d451..0fb49dc15 100644
--- a/js/models/conversations.js
+++ b/js/models/conversations.js
@@ -42,28 +42,40 @@
       if (missing.length) { return "Conversation must have " + missing; }
     },
 
-    sendMessage: function(message, attachments) {
+    sendMessage: function(body, attachments) {
         var now = Date.now();
-        this.messageCollection.add({
-            body           : message,
+        var message = this.messageCollection.add({
+            body           : body,
             conversationId : this.id,
             type           : 'outgoing',
             attachments    : attachments,
             sent_at        : now,
             received_at    : now
-        }).save();
+        });
+        message.save();
 
         this.save({
             unreadCount : 0,
             active_at   : now
         });
 
+        var sendFunc;
         if (this.get('type') == 'private') {
-          return textsecure.messaging.sendMessageToNumber(this.get('id'), message, attachments);
+            sendFunc = textsecure.messaging.sendMessageToNumber;
         }
         else {
-          return textsecure.messaging.sendMessageToGroup(this.get('groupId'), message, attachments);
+            sendFunc = textsecure.messaging.sendMessageToGroup;
         }
+        sendFunc(this.get('id'), body, attachments).catch(function(e) {
+            if (e.name === 'OutgoingIdentityKeyError') {
+                e.args.push(message.id);
+                message.save({ errors : [e] }).then(function() {
+                    extension.trigger('message', message); // notify frontend listeners
+                });
+            } else {
+                throw e;
+            }
+        });
     },
 
     receiveMessage: function(decrypted) {
diff --git a/js/sendmessage.js b/js/sendmessage.js
index 9db62f6d2..519b643e6 100644
--- a/js/sendmessage.js
+++ b/js/sendmessage.js
@@ -114,12 +114,25 @@ window.textsecure.messaging = function() {
 		return Promise.all(promises);
 	}
 
-	var tryMessageAgain = function(number, encodedMessage, callback) {
-		//TODO: Wipe identity key!
-		refreshGroups(number).then(function() {
-			var message = textsecure.protobuf.PushMessageContent.decode(encodedMessage);
-			textsecure.sendMessageProto([number], message, callback);
-		});
+	var tryMessageAgain = function(number, encodedMessage, message_id) {
+        var message = new Whisper.MessageCollection().add({id: message_id});
+        message.fetch().then(function() {
+            textsecure.storage.removeEncrypted("devices" + number);
+            refreshGroups(number).then(function() {
+                var proto = textsecure.protobuf.PushMessageContent.decode(encodedMessage, 'binary');
+                sendMessageProto([number], proto, function(res) {
+                    if (res.failure.length > 0) {
+                        message.set('errors', []);
+                    }
+                    else {
+                        message.set('errors', res.failures);
+                    }
+                    message.save().then(function(){
+                        extension.trigger('message', message); // notify frontend listeners
+                    });
+                });
+            });
+        });
 	};
 	textsecure.replay.registerFunction(tryMessageAgain, textsecure.replay.Type.SEND_MESSAGE);
 
@@ -175,7 +188,7 @@ window.textsecure.messaging = function() {
 							if (error.message !== "Identity key changed")
 								registerError(number, "Failed to reload device keys", error);
 							else {
-                                error = new textsecure.OutgoingIdentityKeyError(encodedNumber, message.encode());
+                                error = new textsecure.OutgoingIdentityKeyError(number, getString(message.encode()));
 								registerError(number, "Identity key changed", error);
 							}
 						});