diff --git a/public/js/controllers/groupsCtrl.js b/public/js/controllers/groupsCtrl.js
index 7db888ccc3..8edb73809e 100644
--- a/public/js/controllers/groupsCtrl.js
+++ b/public/js/controllers/groupsCtrl.js
@@ -192,8 +192,8 @@ habitrpg.controller("GroupsCtrl", ['$scope', '$rootScope', 'Groups', '$http', 'A
 
   }])
 
-  .controller("GuildsCtrl", ['$scope', 'Groups', 'User', '$rootScope', '$state', '$location',
-    function($scope, Groups, User, $rootScope, $state, $location) {
+  .controller("GuildsCtrl", ['$scope', 'Groups', 'User', '$rootScope', '$state', '$location', '$compile',
+    function($scope, Groups, User, $rootScope, $state, $location, $compile) {
       $scope.groups = {
         guilds: Groups.myGuilds(),
         "public": Groups.publicGuilds()
@@ -238,11 +238,12 @@ habitrpg.controller("GroupsCtrl", ['$scope', '$rootScope', 'Groups', '$http', 'A
         })
       }
 
-      $scope.leave = function(group){
-        if (confirm("Are you sure you want to leave this guild?") !== true) {
-          return;
-        }
-        Groups.Group.leave({gid: group._id}, undefined, function(){
+     $scope.leave = function(keep) {
+         if (keep == 'cancel') {
+             $scope.selectedChal = undefined;
+         } else {
+         var group = $scope.selectedGroup;
+             Groups.Group.leave({gid: group._id, keep:keep}, undefined, function(){
           $scope.groups.guilds.splice(_.indexOf($scope.groups.guilds, group), 1);
           // remove user from group members if guild is public so that he can re-join it immediately
           if(group.privacy == 'public' || !group.privacy){ //public guilds with only some fields fetched
@@ -256,6 +257,23 @@ habitrpg.controller("GroupsCtrl", ['$scope', '$rootScope', 'Groups', '$http', 'A
           $state.go('options.social.guilds');
         });
       }
+         $scope.popoverEl.popover('destroy');
+     }
+
+      $scope.clickLeave = function(group, $event){
+          $scope.selectedGroup = group;
+          $scope.popoverEl = $($event.target);
+          var html = $compile(
+              '<a ng-controller="GroupsCtrl" ng-click="leave(\'remove-all\')">Remove Tasks</a><br/>\n<a ng-click="leave(\'keep-all\')">Keep Tasks</a><br/>\n<a ng-click="leave(\'cancel\')">Cancel</a><br/>'
+          )($scope);
+          $scope.popoverEl.popover('destroy').popover({
+              html: true,
+              placement: 'top',
+              trigger: 'manual',
+              title: 'Leaving group challenges and...',
+              content: html
+          }).popover('show');
+      }
 
       $scope.reject = function(guild){
         var i = _.findIndex(User.user.invitations.guilds, {id:guild.id});
diff --git a/src/controllers/groups.js b/src/controllers/groups.js
index 94a4b6e343..f2d8faa36f 100644
--- a/src/controllers/groups.js
+++ b/src/controllers/groups.js
@@ -6,6 +6,7 @@ var async = require('async');
 var shared = require('habitrpg-shared');
 var User = require('./../models/user').model;
 var Group = require('./../models/group').model;
+var Challenge = require('./../models/challenge').model;
 var api = module.exports;
 
 /*
@@ -283,6 +284,8 @@ api.join = function(req, res) {
 api.leave = function(req, res, next) {
   var user = res.locals.user,
     group = res.locals.group;
+  // When removing the user from challenges, should we keep the tasks?
+  var keep = (/^remove-all/i).test(req.query.keep) ? 'remove-all' : 'keep-all';
   async.parallel([
     // Remove active quest from user if they're leaving the party
     function(cb){
@@ -290,6 +293,36 @@ api.leave = function(req, res, next) {
       user.party.quest = Group.cleanQuestProgress();
       user.save(cb);
     },
+    // Remove user from group challenges
+      function(cb){
+        async.waterfall([
+        // Find relevant challenges
+          function(cb) {
+            Challenge.find({$and:[
+              {_id: {$in: user.challenges}}, // Challenges I am in
+              {group: group._id}, // that belong to the group I am leaving
+            ]}, cb);
+          },
+          function(challenges, cb) {
+            // Update each challenge
+            Challenge.update({_id:{$in: _.pluck(challenges, '_id')}},
+                             {$pull:{members:user._id}},
+                             {multi: true}, function(err) {
+                               if (err) return cb(err);
+                               cb(null, challenges);
+                             });
+          },
+          function(challenges, cb) {
+            // Unlink the challenge tasks from user
+            async.waterfall(challenges.map(function(chal) {
+              return function(cb) {
+                user.unlink({cid:chal._id, keep:keep}, function(err){
+                  if (err) return cb(err);
+                  cb(null);
+                });
+             }}), cb);
+          }], cb);
+      },
     function(cb){
       var update = {$pull:{members:user._id}};
       if (group.type == 'party' && group.quest.key){
diff --git a/views/options/social/group.jade b/views/options/social/group.jade
index b1217e0006..a839e8e09d 100644
--- a/views/options/social/group.jade
+++ b/views/options/social/group.jade
@@ -150,7 +150,7 @@ a.pull-right.gem-wallet(popover-trigger='mouseenter', popover-title='Guild Bank'
             input.btn(type='submit', value='Invite')
 
 
-    a.btn.btn-danger(data-id='{{group.id}}', ng-click='leave(group)') Leave
+    a.btn.btn-danger(data-id='{{group.id}}', ng-click='clickLeave(group, $event)') Leave
 
   .span8
     div.blah-options(ng-show='group._editing')
diff --git a/views/options/social/index.jade b/views/options/social/index.jade
index 51d1742dff..44039bcc61 100644
--- a/views/options/social/index.jade
+++ b/views/options/social/index.jade
@@ -37,7 +37,7 @@ script(type='text/ng-template', id='partials/options.social.guilds.public.html')
           li {{group.memberCount}} member(s)
           li
             // join / leave
-            a.btn.btn-small.btn-danger(ng-show='group._isMember', ng-click='leave(group)')
+            a.btn.btn-small.btn-danger(ng-show='group._isMember', ng-click='clickLeave(group, $event)')
               i.icon-ban-circle
               | Leave
             a.btn.btn-small.btn-success(ng-hide='group._isMember', ng-click='join(group)')