diff --git a/dashboard/src/js/client.js b/dashboard/src/js/client.js
index d249552b1..85ee280c1 100644
--- a/dashboard/src/js/client.js
+++ b/dashboard/src/js/client.js
@@ -982,6 +982,15 @@ angular.module('Application').service('Client', ['$http', '$interval', '$timeout
         });
     };
 
+    Client.prototype.ackAppChecklistItem = function (appId, key, acknowledged, callback) {
+        put('/api/v1/apps/' + appId + '/checklist/' + key, { done: acknowledged }, null, function (error, data, status) {
+            if (error) return callback(error);
+            if (status !== 202) return callback(new ClientError(status, data));
+
+            callback(null);
+        });
+    };
+
     Client.prototype.updateApp = function (id, manifest, options, callback) {
         var data =  {
             appStoreId: manifest.id + '@' + manifest.version,
diff --git a/dashboard/src/views/app.html b/dashboard/src/views/app.html
index feea398b5..6a24028b3 100644
--- a/dashboard/src/views/app.html
+++ b/dashboard/src/views/app.html
@@ -742,14 +742,14 @@
           <a href="" class="pull-right" ng-click="info.showDoneChecklist = false" ng-show="info.showDoneChecklist">Hide Checklist</a>
         </p>
 
-        <div ng-repeat="item in app.checklist">
+        <div ng-repeat="(key, item) in app.checklist">
           <div class="checklist-item" ng-hide="item.acknowledged">
             {{ item.message }}
-            <button class="btn btn-xs btn-default btn-outline" ng-click="info.checklistAck(item)"><i class="fas fa-check"></i></button>
+            <button class="btn btn-xs btn-default" ng-click="info.checklistAck(item, key)">Done</button>
           </div>
         </div>
 
-        <div ng-repeat="item in app.checklist" ng-show="info.showDoneChecklist">
+        <div ng-repeat="(key, item) in app.checklist" ng-show="info.showDoneChecklist">
           <div class="checklist-item checklist-item-acknowledged" ng-show="item.acknowledged">
             {{ item.message }}
           </div>
diff --git a/dashboard/src/views/app.js b/dashboard/src/views/app.js
index 703bbc924..a7e7f1fcd 100644
--- a/dashboard/src/views/app.js
+++ b/dashboard/src/views/app.js
@@ -182,11 +182,12 @@ angular.module('Application').controller('AppController', ['$scope', '$location'
             $scope.info.notes.busy = false;
         },
 
-        checklistAck(item) {
+        checklistAck(item, key) {
             item.acknowledged = true;
+            // item.acknowledged = !item.acknowledged;
 
-            Client.configureApp($scope.app.id, 'checklist', { checklist: $scope.app.checklist }, function (error) {
-                if (error) return console.error('Failed to save checklist.', error);
+            Client.ackAppChecklistItem($scope.app.id, key, item.acknowledged, function (error) {
+                if (error) return console.error('Failed to ack checklist item.', error);
                 $scope.info.hasOldChecklist = true;
             });
         }
diff --git a/src/apps.js b/src/apps.js
index 3e641e969..2b62d4384 100644
--- a/src/apps.js
+++ b/src/apps.js
@@ -32,7 +32,7 @@ exports = module.exports = {
     setIcon,
     setTags,
     setNotes,
-    setChecklist,
+    setChecklistItem,
     setMemoryLimit,
     setCpuQuota,
     setMounts,
@@ -1550,11 +1550,22 @@ async function setNotes(app, notes, auditSource) {
     await eventlog.add(eventlog.ACTION_APP_CONFIGURE, auditSource, { appId: app.id, app, notes });
 }
 
-async function setChecklist(app, checklist, auditSource) {
+async function setChecklistItem(app, checklistItemKey, acknowledged, auditSource) {
     assert.strictEqual(typeof app, 'object');
-    assert.strictEqual(typeof checklist, 'object');
+    assert.strictEqual(typeof checklistItemKey, 'string');
+    assert.strictEqual(typeof acknowledged, 'boolean');
     assert.strictEqual(typeof auditSource, 'object');
 
+    if (!app.checklist[checklistItemKey]) throw new BoxError(BoxError.NOT_FOUND, 'no such checklist item');
+
+    // nothing changed
+    if (app.checklist[checklistItemKey].acknowledged === acknowledged) return;
+
+    const checklist = app.checklist;
+    checklist[checklistItemKey].acknowledged = acknowledged;
+    checklist[checklistItemKey].changedAt = Date.now();
+    checklist[checklistItemKey].changedBy = auditSource.username;
+
     await update(app.id, { checklist });
     await eventlog.add(eventlog.ACTION_APP_CONFIGURE, auditSource, { appId: app.id, app, checklist });
 }
diff --git a/src/apptask.js b/src/apptask.js
index 4f3edee65..f040d0fef 100644
--- a/src/apptask.js
+++ b/src/apptask.js
@@ -255,7 +255,10 @@ async function updateChecklist(app, newChecks) {
         const item = {
             acknowledged: false,
             sso: newChecks[k].sso,
-            message: newChecks[k].message
+            appVersion: app.version,
+            message: newChecks[k].message,
+            changedAt: 0,
+            changedBy: null, // username from audit log
         };
 
         if (typeof item.sso === 'undefined') checklist[k] = item;
diff --git a/src/routes/apps.js b/src/routes/apps.js
index d002f2102..c44359594 100644
--- a/src/routes/apps.js
+++ b/src/routes/apps.js
@@ -24,7 +24,6 @@ exports = module.exports = {
     setLabel,
     setTags,
     setNotes,
-    setChecklist,
     setIcon,
     setTurn,
     setRedis,
@@ -43,6 +42,8 @@ exports = module.exports = {
     setMounts,
     setUpstreamUri,
 
+    setChecklistItem,
+
     stop,
     start,
     restart,
@@ -271,16 +272,16 @@ async function setNotes(req, res, next) {
     next(new HttpSuccess(200, {}));
 }
 
-async function setChecklist(req, res, next) {
+async function setChecklistItem(req, res, next) {
     assert.strictEqual(typeof req.body, 'object');
     assert.strictEqual(typeof req.app, 'object');
 
-    if (typeof req.body.checklist !== 'object') return next(new HttpError(400, 'checklist must be an object'));
+    if (typeof req.body.done !== 'boolean') return next(new HttpError(400, 'done must be a boolean'));
 
-    const [error] = await safe(apps.setChecklist(req.app, req.body.checklist, AuditSource.fromRequest(req)));
+    const [error] = await safe(apps.setChecklistItem(req.app, req.params.key, req.body.done, AuditSource.fromRequest(req)));
     if (error) return next(BoxError.toHttpError(error));
 
-    next(new HttpSuccess(200, {}));
+    next(new HttpSuccess(202, {}));
 }
 
 async function setIcon(req, res, next) {
diff --git a/src/server.js b/src/server.js
index 34838b30a..be0998f1a 100644
--- a/src/server.js
+++ b/src/server.js
@@ -247,7 +247,6 @@ async function initializeExpressSync() {
     router.post('/api/v1/apps/:id/configure/tags',               json, token, routes.apps.load, authorizeOperator, routes.apps.setTags);
     router.post('/api/v1/apps/:id/configure/icon',               json, token, routes.apps.load, authorizeOperator, routes.apps.setIcon);
     router.post('/api/v1/apps/:id/configure/notes',              json, token, routes.apps.load, authorizeOperator, routes.apps.setNotes);
-    router.post('/api/v1/apps/:id/configure/checklist',          json, token, routes.apps.load, authorizeOperator, routes.apps.setChecklist);
     router.post('/api/v1/apps/:id/configure/memory_limit',       json, token, routes.apps.load, authorizeOperator, routes.apps.setMemoryLimit);
     router.post('/api/v1/apps/:id/configure/cpu_quota',          json, token, routes.apps.load, authorizeOperator, routes.apps.setCpuQuota);
     router.post('/api/v1/apps/:id/configure/automatic_backup',   json, token, routes.apps.load, authorizeOperator, routes.apps.setAutomaticBackup);
@@ -275,6 +274,7 @@ async function initializeExpressSync() {
     router.get ('/api/v1/apps/:id/backups',                            token, routes.apps.load, authorizeOperator, routes.apps.listBackups);
     router.post('/api/v1/apps/:id/backups/:backupId',            json, token, routes.apps.load, authorizeOperator, routes.apps.updateBackup);
     router.get ('/api/v1/apps/:id/backups/:backupId/download',         token, routes.apps.load, authorizeOperator, routes.apps.downloadBackup);
+    router.put ('/api/v1/apps/:id/checklist/:key',               json, token, routes.apps.load, authorizeOperator, routes.apps.setChecklistItem);
     router.post('/api/v1/apps/:id/start',                        json, token, routes.apps.load, authorizeOperator, routes.apps.start);
     router.post('/api/v1/apps/:id/stop',                         json, token, routes.apps.load, authorizeOperator, routes.apps.stop);
     router.post('/api/v1/apps/:id/restart',                      json, token, routes.apps.load, authorizeOperator, routes.apps.restart);