diff --git a/app/assets/javascripts/discourse/components/global-notice.js.es6 b/app/assets/javascripts/discourse/components/global-notice.js.es6
index f61798163fb..13994f28fbf 100644
--- a/app/assets/javascripts/discourse/components/global-notice.js.es6
+++ b/app/assets/javascripts/discourse/components/global-notice.js.es6
@@ -17,6 +17,14 @@ export default Ember.Component.extend(StringBuffer, {
       notices.push([I18n.t("emails_are_disabled"), 'alert-emails-disabled']);
     }
 
+    if (this.currentUser && this.currentUser.get('staff') && this.siteSettings.bootstrap_mode_enabled) {
+      if (this.siteSettings.bootstrap_mode_min_users > 0) {
+        notices.push([I18n.t("bootstrap_mode_enabled", {min_users: this.siteSettings.bootstrap_mode_min_users}), 'alert-bootstrap-mode']);
+      } else {
+        notices.push([I18n.t("bootstrap_mode_disabled"), 'alert-bootstrap-mode']);
+      }
+    }
+
     if (!_.isEmpty(this.siteSettings.global_notice)) {
       notices.push([this.siteSettings.global_notice, 'alert-global-notice']);
     }
diff --git a/app/controllers/admin/site_settings_controller.rb b/app/controllers/admin/site_settings_controller.rb
index b8170147800..30ad7cd4af6 100644
--- a/app/controllers/admin/site_settings_controller.rb
+++ b/app/controllers/admin/site_settings_controller.rb
@@ -10,9 +10,7 @@ class Admin::SiteSettingsController < Admin::AdminController
     value = params[id]
     value.strip! if value.is_a?(String)
     begin
-      prev_value = SiteSetting.send(id)
-      SiteSetting.set(id, value)
-      StaffActionLogger.new(current_user).log_site_setting_change(id, prev_value, value) if SiteSetting.has_setting?(id)
+      SiteSetting.set_and_log(id, value, current_user)
       render nothing: true
     rescue Discourse::InvalidParameters => e
       render json: {errors: [e.message]}, status: 422
diff --git a/app/jobs/regular/enable_bootstrap_mode.rb b/app/jobs/regular/enable_bootstrap_mode.rb
new file mode 100644
index 00000000000..fcbd5b2921f
--- /dev/null
+++ b/app/jobs/regular/enable_bootstrap_mode.rb
@@ -0,0 +1,18 @@
+module Jobs
+  class EnableBootstrapMode < Jobs::Base
+    sidekiq_options queue: 'critical'
+
+    def execute(args)
+      raise Discourse::InvalidParameters.new(:user_id) unless args[:user_id].present?
+      return if SiteSetting.bootstrap_mode_enabled
+
+      user = User.find_by(id: args[:user_id])
+      return unless user.is_singular_admin?
+
+      # let's enable bootstrap mode settings
+      SiteSetting.set_and_log('default_trust_level', TrustLevel[1])
+      SiteSetting.set_and_log('default_email_digest_frequency', 1440)
+      SiteSetting.set_and_log('bootstrap_mode_enabled', true)
+    end
+  end
+end
diff --git a/app/jobs/scheduled/disable_bootstrap_mode.rb b/app/jobs/scheduled/disable_bootstrap_mode.rb
new file mode 100644
index 00000000000..ae1707c37f2
--- /dev/null
+++ b/app/jobs/scheduled/disable_bootstrap_mode.rb
@@ -0,0 +1,16 @@
+module Jobs
+  class DisableBootstrapMode < Jobs::Scheduled
+    every 1.day
+
+    def execute(args)
+      return unless SiteSetting.bootstrap_mode_enabled
+      total_users = User.where.not(id: Discourse::SYSTEM_USER_ID).count
+
+      if SiteSetting.bootstrap_mode_min_users == 0 || total_users > SiteSetting.bootstrap_mode_min_users
+        SiteSetting.set_and_log('default_trust_level', TrustLevel[0])
+        SiteSetting.set_and_log('default_email_digest_frequency', 10080)
+        SiteSetting.set_and_log('bootstrap_mode_enabled', false)
+      end
+    end
+  end
+end
diff --git a/app/models/user.rb b/app/models/user.rb
index db2e267ae0d..8d68c337b07 100644
--- a/app/models/user.rb
+++ b/app/models/user.rb
@@ -845,6 +845,10 @@ class User < ActiveRecord::Base
       custom_fields["master_id"].to_i > 0
   end
 
+  def is_singular_admin?
+    User.where(admin: true).where.not(id: id).where.not(id: Discourse::SYSTEM_USER_ID).blank?
+  end
+
   protected
 
   def badge_grant
diff --git a/config/locales/client.en.yml b/config/locales/client.en.yml
index d58b84c7c22..482b17ee354 100644
--- a/config/locales/client.en.yml
+++ b/config/locales/client.en.yml
@@ -147,6 +147,9 @@ en:
 
     emails_are_disabled: "All outgoing email has been globally disabled by an administrator. No email notifications of any kind will be sent."
 
+    bootstrap_mode_enabled: "To make launching your new site easier, you are in bootstrap mode. All new users will be granted trust level 1 and have daily email digest updates enabled. This will be automatically turned off when total user count exceeds %{min_users} users."
+    bootstrap_mode_disabled: "Bootstrap mode will be disabled in next 24 hours."
+
     s3:
       regions:
         us_east_1: "US East (N. Virginia)"
diff --git a/config/locales/server.en.yml b/config/locales/server.en.yml
index 55aff601897..4b19733f5ae 100644
--- a/config/locales/server.en.yml
+++ b/config/locales/server.en.yml
@@ -1272,6 +1272,8 @@ en:
 
     delete_drafts_older_than_n_days: Delete drafts older than (n) days.
 
+    bootstrap_mode_min_users: "Minimum number of users required to disable bootstrap mode (set to 0 to disable)"
+
     vacuum_db_days: "Run VACUUM ANALYZE to reclaim DB space after migrations (set to 0 to disable)"
 
     prevent_anons_from_downloading_files: "Prevent anonymous users from downloading attachments. WARNING: this will prevent any non-image site assets posted as attachments from working."
diff --git a/config/site_settings.yml b/config/site_settings.yml
index bc2bb0708b6..ea6fdf53240 100644
--- a/config/site_settings.yml
+++ b/config/site_settings.yml
@@ -1090,6 +1090,17 @@ uncategorized:
     default: -1
     hidden: true
 
+  bootstrap_mode_min_users:
+    default: 50
+    client: true
+    min: 0
+    max: 5000
+
+  bootstrap_mode_enabled:
+    default: false
+    client: true
+    hidden: true
+
   automatically_unpin_topics:
     default: true
     client: true
diff --git a/lib/auth/default_current_user_provider.rb b/lib/auth/default_current_user_provider.rb
index 1e5cec773a3..0bc2bf34e76 100644
--- a/lib/auth/default_current_user_provider.rb
+++ b/lib/auth/default_current_user_provider.rb
@@ -68,6 +68,7 @@ class Auth::DefaultCurrentUserProvider
     end
     cookies.permanent[TOKEN_COOKIE] = { value: user.auth_token, httponly: true }
     make_developer_admin(user)
+    enable_bootstrap_mode(user)
     @env[CURRENT_USER_KEY] = user
   end
 
@@ -81,6 +82,10 @@ class Auth::DefaultCurrentUserProvider
     end
   end
 
+  def enable_bootstrap_mode(user)
+    Jobs.enqueue(:enable_bootstrap_mode, user_id: user.id) if user.admin && user.last_seen_at.nil? && !SiteSetting.bootstrap_mode_enabled && user.is_singular_admin?
+  end
+
   def log_off_user(session, cookies)
     if SiteSetting.log_out_strict && (user = current_user)
       user.auth_token = nil
diff --git a/lib/site_setting_extension.rb b/lib/site_setting_extension.rb
index 90870a46734..4395a8c9075 100644
--- a/lib/site_setting_extension.rb
+++ b/lib/site_setting_extension.rb
@@ -371,6 +371,12 @@ module SiteSettingExtension
     end
   end
 
+  def set_and_log(name, value, user=Discourse.system_user)
+    prev_value = send(name)
+    set(name, value)
+    StaffActionLogger.new(user).log_site_setting_change(name, prev_value, value) if has_setting?(name)
+  end
+
   protected
 
   def clear_cache!
diff --git a/spec/controllers/categories_controller_spec.rb b/spec/controllers/categories_controller_spec.rb
index d9d9240b544..4850d5f36ac 100644
--- a/spec/controllers/categories_controller_spec.rb
+++ b/spec/controllers/categories_controller_spec.rb
@@ -64,7 +64,7 @@ describe CategoriesController do
           expect(category.slug).to eq("hello-cat")
           expect(category.color).to eq("ff0")
           expect(category.auto_close_hours).to eq(72)
-          expect(UserHistory.count).to eq(1)
+          expect(UserHistory.count).to eq(4) # 1 + 3 (bootstrap mode)
         end
       end
     end
@@ -228,7 +228,7 @@ describe CategoriesController do
               "everyone" => CategoryGroup.permission_types[:create_post]
             }
 
-          expect(UserHistory.count).to eq(2)
+          expect(UserHistory.count).to eq(5) # 2 + 3 (bootstrap mode)
         end
       end
     end
diff --git a/spec/controllers/uploads_controller_spec.rb b/spec/controllers/uploads_controller_spec.rb
index 4a57897e771..90c3426b17d 100644
--- a/spec/controllers/uploads_controller_spec.rb
+++ b/spec/controllers/uploads_controller_spec.rb
@@ -77,9 +77,8 @@ describe UploadsController do
       end
 
       it 'correctly sets retain_hours for admins' do
-        Jobs.expects(:enqueue).with(:create_thumbnails, anything)
-
         log_in :admin
+        Jobs.expects(:enqueue).with(:create_thumbnails, anything)
 
         message = MessageBus.track_publish do
           xhr :post, :create, file: logo, retain_hours: 100, type: "profile_background"
diff --git a/spec/jobs/disable_bootstrap_mode_spec.rb b/spec/jobs/disable_bootstrap_mode_spec.rb
new file mode 100644
index 00000000000..96f11ceac3f
--- /dev/null
+++ b/spec/jobs/disable_bootstrap_mode_spec.rb
@@ -0,0 +1,33 @@
+require 'rails_helper'
+
+describe Jobs::DisableBootstrapMode do
+
+  context '.execute' do
+    let(:admin) { Fabricate(:admin) }
+
+    before do
+      SiteSetting.bootstrap_mode_enabled = true
+    end
+
+    it 'does not execute if bootstrap mode is already disabled' do
+      SiteSetting.bootstrap_mode_enabled = false
+      StaffActionLogger.any_instance.expects(:log_site_setting_change).never
+      Jobs::DisableBootstrapMode.new.execute(user_id: admin.id)
+    end
+
+    it 'turns off bootstrap mode if bootstrap_mode_min_users is set to 0' do
+      SiteSetting.bootstrap_mode_min_users = 0
+      StaffActionLogger.any_instance.expects(:log_site_setting_change).times(3)
+      Jobs::DisableBootstrapMode.new.execute(user_id: admin.id)
+    end
+
+    it 'successfully turns off bootstrap mode' do
+      SiteSetting.bootstrap_mode_min_users = 5
+      6.times do
+        Fabricate(:user)
+      end
+      StaffActionLogger.any_instance.expects(:log_site_setting_change).times(3)
+      Jobs::DisableBootstrapMode.new.execute(user_id: admin.id)
+    end
+  end
+end
diff --git a/spec/jobs/enable_bootstrap_mode_spec.rb b/spec/jobs/enable_bootstrap_mode_spec.rb
new file mode 100644
index 00000000000..c0441bc5fc4
--- /dev/null
+++ b/spec/jobs/enable_bootstrap_mode_spec.rb
@@ -0,0 +1,33 @@
+require 'rails_helper'
+
+describe Jobs::EnableBootstrapMode do
+
+  context '.execute' do
+    let(:admin) { Fabricate(:admin) }
+
+    before do
+      SiteSetting.bootstrap_mode_enabled = false
+    end
+
+    it 'raises an error when user_id is missing' do
+      expect { Jobs::EnableBootstrapMode.new.execute({}) }.to raise_error(Discourse::InvalidParameters)
+    end
+
+    it 'does not execute if bootstrap mode is already enabled' do
+      SiteSetting.bootstrap_mode_enabled = true
+      StaffActionLogger.any_instance.expects(:log_site_setting_change).never
+      Jobs::EnableBootstrapMode.new.execute(user_id: admin.id)
+    end
+
+    it 'does not turn on bootstrap mode if first admin already exists' do
+      first_admin = Fabricate(:admin)
+      StaffActionLogger.any_instance.expects(:log_site_setting_change).never
+      Jobs::EnableBootstrapMode.new.execute(user_id: admin.id)
+    end
+
+    it 'successfully turns on bootstrap mode' do
+      StaffActionLogger.any_instance.expects(:log_site_setting_change).times(3)
+      Jobs::EnableBootstrapMode.new.execute(user_id: admin.id)
+    end
+  end
+end
diff --git a/spec/models/user_spec.rb b/spec/models/user_spec.rb
index 42575c62f57..92e12e9e71e 100644
--- a/spec/models/user_spec.rb
+++ b/spec/models/user_spec.rb
@@ -330,6 +330,20 @@ describe User do
     end
   end
 
+  describe '.is_singular_admin?' do
+    it 'returns true if user is singular admin' do
+      admin = Fabricate(:admin)
+      expect(admin.is_singular_admin?).to eq(true)
+    end
+
+    it 'returns false if user is not the only admin' do
+      admin = Fabricate(:admin)
+      second_admin = Fabricate(:admin)
+
+      expect(admin.is_singular_admin?).to eq(false)
+    end
+  end
+
   describe 'name heuristics' do
     it 'is able to guess a decent name from an email' do
       expect(User.suggest_name('sam.saffron@gmail.com')).to eq('Sam Saffron')