diff --git a/test/api/v3/unit/models/group.test.js b/test/api/v3/unit/models/group.test.js
index b11f8dc9a4..d198c4690f 100644
--- a/test/api/v3/unit/models/group.test.js
+++ b/test/api/v3/unit/models/group.test.js
@@ -1061,8 +1061,45 @@ describe('Group Model', () => {
           [nonParticipatingMember._id]: false,
           [undecidedMember._id]: null,
         };
+      });
 
-        sandbox.spy(User, 'update');
+      describe('user update retry failures', () => {
+        let successfulMock = {
+          exec: () => {
+            return Promise.resolve({raw: 'sucess'});
+          },
+        };
+        let failedMock = {
+          exec: () => {
+            return Promise.reject(new Error('error'));
+          },
+        };
+
+        it('doesn\'t retry successful operations', async () => {
+          sandbox.stub(User, 'update').returns(successfulMock);
+
+          await party.finishQuest(quest);
+
+          expect(User.update).to.be.calledTwice;
+        });
+
+        it('stops retrying when a successful update has occurred', async () => {
+          let updateStub = sandbox.stub(User, 'update');
+          updateStub.onCall(0).returns(failedMock);
+          updateStub.returns(successfulMock);
+
+          await party.finishQuest(quest);
+
+          expect(User.update).to.be.calledThrice;
+        });
+
+        it('retries failed updates at most five times per user', async () => {
+          sandbox.stub(User, 'update').returns(failedMock);
+
+          await expect(party.finishQuest(quest)).to.eventually.be.rejected;
+
+          expect(User.update.callCount).to.eql(10);
+        });
       });
 
       it('gives out achievements', async () => {
@@ -1171,13 +1208,15 @@ describe('Group Model', () => {
 
       context('Party quests', () => {
         it('updates participating members with rewards', async () => {
+          sandbox.spy(User, 'update');
           await party.finishQuest(quest);
 
-          expect(User.update).to.be.calledOnce;
+          expect(User.update).to.be.calledTwice;
           expect(User.update).to.be.calledWithMatch({
-            _id: {
-              $in: [questLeader._id, participatingMember._id],
-            },
+            _id: questLeader._id,
+          });
+          expect(User.update).to.be.calledWithMatch({
+            _id: participatingMember._id,
           });
         });
 
@@ -1204,6 +1243,7 @@ describe('Group Model', () => {
         });
 
         it('updates all users with rewards', async () => {
+          sandbox.spy(User, 'update');
           await party.finishQuest(tavernQuest);
 
           expect(User.update).to.be.calledOnce;
diff --git a/website/server/models/group.js b/website/server/models/group.js
index d04d3c9506..e310d1a21d 100644
--- a/website/server/models/group.js
+++ b/website/server/models/group.js
@@ -38,6 +38,7 @@ const LARGE_GROUP_COUNT_MESSAGE_CUTOFF = shared.constants.LARGE_GROUP_COUNT_MESS
 
 const CRON_SAFE_MODE = nconf.get('CRON_SAFE_MODE') === 'true';
 const CRON_SEMI_SAFE_MODE = nconf.get('CRON_SEMI_SAFE_MODE') === 'true';
+const MAX_UPDATE_RETRIES = 5;
 
 export let schema = new Schema({
   name: {type: String, required: true},
@@ -577,6 +578,19 @@ schema.statics.cleanGroupQuest = function cleanGroupQuest () {
   };
 };
 
+async function _updateUserWithRetries (userId, updates, numTry = 1) {
+  return await User.update({_id: userId}, updates).exec()
+    .then((raw) => {
+      return raw;
+    }).catch((err) => {
+      if (numTry < MAX_UPDATE_RETRIES) {
+        return _updateUserWithRetries(userId, updates, ++numTry);
+      } else {
+        throw err;
+      }
+    });
+}
+
 // Participants: Grant rewards & achievements, finish quest.
 // Changes the group object update members
 schema.methods.finishQuest = async function finishQuest (quest) {
@@ -623,11 +637,19 @@ schema.methods.finishQuest = async function finishQuest (quest) {
     }
   });
 
-  let q = this._id === TAVERN_ID ? {} : {_id: {$in: this.getParticipatingQuestMembers()}};
+  let participants = this._id === TAVERN_ID ? {} : this.getParticipatingQuestMembers();
   this.quest = {};
   this.markModified('quest');
 
-  return await User.update(q, updates, {multi: true}).exec();
+  if (this._id === TAVERN_ID) {
+    return await User.update({}, updates, {multi: true}).exec();
+  }
+
+  let promises = participants.map(userId => {
+    return _updateUserWithRetries(userId, updates);
+  });
+
+  return Bluebird.all(promises);
 };
 
 function _isOnQuest (user, progress, group) {