diff --git a/CHANGELOG b/CHANGELOG
index 2f02b9dc265..090b54f41a4 100644
--- a/CHANGELOG
+++ b/CHANGELOG
@@ -2,6 +2,7 @@ Please view this file on the master branch, on stable branches it's out of date.
 
 v 8.3.0 (unreleased)
   - Fix Error 500 when viewing user's personal projects from admin page (Stan Hu)
+  - Ensure cached application settings are refreshed at startup (Stan Hu)
   - Fix: Assignee selector is empty when 'Unassigned' is selected (Jose Corcuera)
   - Fix 500 error when update group member permission
   - Fix: Raw private snippets access workflow
diff --git a/app/models/application_setting.rb b/app/models/application_setting.rb
index b2d5fe1558f..3df8135acf1 100644
--- a/app/models/application_setting.rb
+++ b/app/models/application_setting.rb
@@ -73,15 +73,23 @@ class ApplicationSetting < ActiveRecord::Base
   end
 
   after_commit do
-    Rails.cache.write('application_setting.last', self)
+    Rails.cache.write(cache_key, self)
   end
 
   def self.current
-    Rails.cache.fetch('application_setting.last') do
+    Rails.cache.fetch(cache_key) do
       ApplicationSetting.last
     end
   end
 
+  def self.expire
+    Rails.cache.delete(cache_key)
+  end
+
+  def self.cache_key
+    'application_setting.last'
+  end
+
   def self.create_from_defaults
     create(
       default_projects_limit: Settings.gitlab['default_projects_limit'],
diff --git a/app/models/ci/application_setting.rb b/app/models/ci/application_setting.rb
index 1307fa0b472..4e512d290ee 100644
--- a/app/models/ci/application_setting.rb
+++ b/app/models/ci/application_setting.rb
@@ -14,11 +14,15 @@ module Ci
     extend Ci::Model
 
     after_commit do
-      Rails.cache.write('ci_application_setting.last', self)
+      Rails.cache.write(cache_key, self)
+    end
+
+    def self.expire
+      Rails.cache.delete(cache_key)
     end
 
     def self.current
-      Rails.cache.fetch('ci_application_setting.last') do
+      Rails.cache.fetch(cache_key) do
         Ci::ApplicationSetting.last
       end
     end
@@ -29,5 +33,9 @@ module Ci
         add_pusher: Settings.gitlab_ci['add_pusher'],
       )
     end
+
+    def self.cache_key
+      'ci_application_setting.last'
+    end
   end
 end
diff --git a/config/initializers/1_settings.rb b/config/initializers/1_settings.rb
index b162b8a83fc..444e91109df 100644
--- a/config/initializers/1_settings.rb
+++ b/config/initializers/1_settings.rb
@@ -293,3 +293,12 @@ if Rails.env.test?
   Settings.gitlab['default_can_create_group'] = true
   Settings.gitlab['default_can_create_team']  = false
 end
+
+# Force a refresh of application settings at startup
+begin
+  ApplicationSetting.expire
+  Ci::ApplicationSetting.expire
+rescue
+  # Gracefully handle when Redis is not available. For example,
+  # omnibus may fail here during assets:precompile.
+end