diff --git a/test/api/groups.coffee b/test/api/groups.coffee
index 2daa783645..2c2674bbdf 100644
--- a/test/api/groups.coffee
+++ b/test/api/groups.coffee
@@ -11,7 +11,7 @@ describe "Guilds", ->
       registerNewUser ->
         User.findByIdAndUpdate user._id,
           $set:
-            "balance": 10
+            "balance": 40
           , (err, _user) ->
             done()
       , true
@@ -150,6 +150,28 @@ describe "Guilds", ->
           expectCode res, 204
           done()
 
+    it "deletes a group when the last member leaves", (done) ->
+      groupToDeleteAfterLeave = undefined
+      request.post(baseURL + "/groups").send(
+        name: "TestGroupToDeleteAfteLeave"
+        type: "guild"
+        privacy: "private"
+      ).end (res) ->
+        groupToDeleteAfterLeave = res.body
+        async.waterfall [
+          (cb) ->
+            request.post(baseURL + "/groups/" + groupToDeleteAfterLeave._id + "/leave")
+            .end (res) ->
+              expectCode res, 204
+              cb()
+
+          (cb) ->
+            request.post(baseURL + "/groups/" + groupToDeleteAfterLeave._id)
+            .end (res) ->
+              expectCode res, 404
+              cb()
+        ], done
+
   context "removing users groups", ->
     it "allows guild leaders to remove a member (but not themselves)", (done) ->
       guildToRemoveMember = undefined
diff --git a/website/src/controllers/groups.js b/website/src/controllers/groups.js
index 64b45da0e8..774037b8c0 100644
--- a/website/src/controllers/groups.js
+++ b/website/src/controllers/groups.js
@@ -511,8 +511,77 @@ api.leave = function(req, res, next) {
 
   // When removing the user from challenges, should we keep the tasks?
   var keep = (/^remove-all/i).test(req.query.keep) ? 'remove-all' : 'keep-all';
-
-  group.leave(user, keep, function(err){
+  async.parallel([
+    // Remove active quest from user if they're leaving the party
+    function(cb){
+      if (group.type != 'party') return cb(null,{},1);
+      user.party.quest = Group.cleanQuestProgress();
+      user.save(cb);
+    },
+    // Remove user from group challenges
+    function(cb){
+      async.waterfall([
+        // Find relevant challenges
+        function(cb2) {
+          Challenge.find({
+            _id: {$in: user.challenges}, // Challenges I am in
+            group: group._id // that belong to the group I am leaving
+          }, cb2);
+        },
+        // Update each challenge
+        function(challenges, cb2) {
+          Challenge.update(
+            {_id:{$in: _.pluck(challenges, '_id')}},
+            {$pull:{members:user._id}},
+            {multi: true},
+            function(err) {
+             cb2(err, challenges); // pass `challenges` above to cb
+            }
+          );
+        },
+        // Unlink the challenge tasks from user
+        function(challenges, cb2) {
+          async.waterfall(challenges.map(function(chal) {
+            return function(cb3) {
+              var i = user.challenges.indexOf(chal._id)
+              if (~i) user.challenges.splice(i,1);
+              user.unlink({cid:chal._id, keep:keep}, cb3);
+            }
+          }), cb2);
+        }
+      ], cb);
+    },
+    // Update the group
+    function(cb){
+      var update = {$pull:{members:user._id}};
+      if (group.type == 'party' && group.quest.key){
+        update['$unset'] = {};
+        update['$unset']['quest.members.' + user._id] = 1;
+      }
+      // FIXME do we want to remove the group `if group.members.length == 0` ? (well, 1 since the update hasn't gone through yet)
+      if (group.members.length > 1) {
+        var seniorMember = _.find(group.members, function (m) {return m != user._id});
+        // If the leader is leaving (or if the leader previously left, and this wasn't accounted for)
+        var leader = group.leader;
+        if (leader == user._id || !~group.members.indexOf(leader)) {
+          update['$set'] = update['$set'] || {};
+          update['$set'].leader = seniorMember;
+        }
+        leader = group.quest && group.quest.leader;
+        if (leader && (leader == user._id || !~group.members.indexOf(leader))) {
+          update['$set'] = update['$set'] || {};
+          update['$set']['quest.leader'] = seniorMember;
+        }
+        update['$inc'] = {memberCount: -1};
+        Group.update({_id:group._id}, update, cb);
+      } else if (group.members.length === 1) {
+        //We don't delete public groups when they are empty
+        if (group.privacy === 'private' || group.type === 'party') {
+          Group.remove({_id:group._id}, cb);
+        }
+      }
+    }
+  ],function(err){
     if (err) return next(err);
     user = group = keep = null;
     return res.send(204);