diff --git a/app/assets/javascripts/admin/components/site-settings-image-uploader.js.es6 b/app/assets/javascripts/admin/components/site-settings-image-uploader.js.es6
new file mode 100644
index 00000000000..4ebb3e8e13e
--- /dev/null
+++ b/app/assets/javascripts/admin/components/site-settings-image-uploader.js.es6
@@ -0,0 +1,6 @@
+import ImageUploader from "discourse/components/image-uploader";
+
+export default ImageUploader.extend({
+  layoutName: "components/image-uploader",
+  uploadUrlParams: "&for_site_setting=true"
+});
diff --git a/app/assets/javascripts/admin/mixins/setting-component.js.es6 b/app/assets/javascripts/admin/mixins/setting-component.js.es6
index 9408bfbceba..1d6184c85e5 100644
--- a/app/assets/javascripts/admin/mixins/setting-component.js.es6
+++ b/app/assets/javascripts/admin/mixins/setting-component.js.es6
@@ -12,7 +12,8 @@ const CUSTOM_TYPES = [
   "category",
   "uploaded_image_list",
   "compact_list",
-  "secret_list"
+  "secret_list",
+  "upload"
 ];
 
 export default Ember.Mixin.create({
diff --git a/app/assets/javascripts/admin/templates/components/site-settings/upload.hbs b/app/assets/javascripts/admin/templates/components/site-settings/upload.hbs
new file mode 100644
index 00000000000..d13892157db
--- /dev/null
+++ b/app/assets/javascripts/admin/templates/components/site-settings/upload.hbs
@@ -0,0 +1,2 @@
+{{site-settings-image-uploader imageUrl=value type="site_setting"}}
+<div class='desc'>{{{unbound setting.description}}}</div>
diff --git a/app/assets/javascripts/discourse.js.es6 b/app/assets/javascripts/discourse.js.es6
index e66abede413..e84865fb6bb 100644
--- a/app/assets/javascripts/discourse.js.es6
+++ b/app/assets/javascripts/discourse.js.es6
@@ -62,7 +62,7 @@ const Discourse = Ember.Application.extend({
   @observes("notifyCount")
   faviconChanged() {
     if (Discourse.User.currentProp("dynamic_favicon")) {
-      let url = Discourse.SiteSettings.favicon_url;
+      let url = Discourse.SiteSettings.site_favicon_url;
       if (/^http/.test(url)) {
         url = Discourse.getURL("/favicon/proxied?" + encodeURIComponent(url));
       }
diff --git a/app/assets/javascripts/discourse/lib/desktop-notifications.js.es6 b/app/assets/javascripts/discourse/lib/desktop-notifications.js.es6
index 33a594360d4..06264d5c199 100644
--- a/app/assets/javascripts/discourse/lib/desktop-notifications.js.es6
+++ b/app/assets/javascripts/discourse/lib/desktop-notifications.js.es6
@@ -70,8 +70,8 @@ function confirmNotification() {
     {
       body: I18n.t("notifications.popup.confirm_body"),
       icon:
-        Discourse.SiteSettings.logo_small_url ||
-        Discourse.SiteSettings.logo_url,
+        Discourse.SiteSettings.site_logo_small_url ||
+        Discourse.SiteSettings.site_logo_url,
       tag: "confirm-subscription"
     }
   );
@@ -150,8 +150,11 @@ function onNotification(data) {
   });
 
   const notificationBody = data.excerpt;
+
   const notificationIcon =
-    Discourse.SiteSettings.logo_small_url || Discourse.SiteSettings.logo_url;
+    Discourse.SiteSettings.site_logo_small_url ||
+    Discourse.SiteSettings.site_logo_url;
+
   const notificationTag =
     "discourse-notification-" +
     Discourse.SiteSettings.title +
diff --git a/app/assets/javascripts/discourse/mixins/upload.js.es6 b/app/assets/javascripts/discourse/mixins/upload.js.es6
index eac1fcff186..4d89f1ab912 100644
--- a/app/assets/javascripts/discourse/mixins/upload.js.es6
+++ b/app/assets/javascripts/discourse/mixins/upload.js.es6
@@ -22,10 +22,13 @@ export default Em.Mixin.create({
       ".json?client_id=" +
       (this.messageBus && this.messageBus.clientId) +
       "&authenticity_token=" +
-      encodeURIComponent(Discourse.Session.currentProp("csrfToken"))
+      encodeURIComponent(Discourse.Session.currentProp("csrfToken")) +
+      this.uploadUrlParams
     );
   },
 
+  uploadUrlParams: "",
+
   uploadOptions() {
     return {};
   },
diff --git a/app/assets/javascripts/discourse/widgets/home-logo.js.es6 b/app/assets/javascripts/discourse/widgets/home-logo.js.es6
index 6a9a0f1aa2c..c0532d14712 100644
--- a/app/assets/javascripts/discourse/widgets/home-logo.js.es6
+++ b/app/assets/javascripts/discourse/widgets/home-logo.js.es6
@@ -20,14 +20,14 @@ export default createWidget("home-logo", {
     const { siteSettings } = this;
     const mobileView = this.site.mobileView;
 
-    const mobileLogoUrl = siteSettings.mobile_logo_url || "";
+    const mobileLogoUrl = siteSettings.site_mobile_logo_url || "";
     const showMobileLogo = mobileView && mobileLogoUrl.length > 0;
 
-    const logoUrl = siteSettings.logo_url || "";
+    const logoUrl = siteSettings.site_logo_url || "";
     const title = siteSettings.title;
 
     if (!mobileView && this.attrs.minimized) {
-      const logoSmallUrl = siteSettings.logo_small_url || "";
+      const logoSmallUrl = siteSettings.site_logo_small_url || "";
       if (logoSmallUrl.length) {
         return h("img#site-logo.logo-small", {
           key: "logo-small",
diff --git a/app/assets/javascripts/wizard/components/image-preview-apple-touch-icon-url.js.es6 b/app/assets/javascripts/wizard/components/image-preview-apple-touch-icon.js.es6
similarity index 100%
rename from app/assets/javascripts/wizard/components/image-preview-apple-touch-icon-url.js.es6
rename to app/assets/javascripts/wizard/components/image-preview-apple-touch-icon.js.es6
diff --git a/app/assets/javascripts/wizard/components/image-preview-favicon-url.js.es6 b/app/assets/javascripts/wizard/components/image-preview-favicon.js.es6
similarity index 100%
rename from app/assets/javascripts/wizard/components/image-preview-favicon-url.js.es6
rename to app/assets/javascripts/wizard/components/image-preview-favicon.js.es6
diff --git a/app/assets/javascripts/wizard/components/image-preview-logo-small-url.js.es6 b/app/assets/javascripts/wizard/components/image-preview-logo-small.js.es6
similarity index 100%
rename from app/assets/javascripts/wizard/components/image-preview-logo-small-url.js.es6
rename to app/assets/javascripts/wizard/components/image-preview-logo-small.js.es6
diff --git a/app/assets/javascripts/wizard/components/image-preview-logo-url.js.es6 b/app/assets/javascripts/wizard/components/image-preview-logo.js.es6
similarity index 100%
rename from app/assets/javascripts/wizard/components/image-preview-logo-url.js.es6
rename to app/assets/javascripts/wizard/components/image-preview-logo.js.es6
diff --git a/app/assets/stylesheets/common/admin/settings.scss b/app/assets/stylesheets/common/admin/settings.scss
index 53921f04e7a..b42348f12d6 100644
--- a/app/assets/stylesheets/common/admin/settings.scss
+++ b/app/assets/stylesheets/common/admin/settings.scss
@@ -37,6 +37,10 @@
           width: 100% !important; // !important overrides hard-coded mobile width of 68px
         }
       }
+      .uploaded-image-preview {
+        background-size: auto;
+        background-repeat: no-repeat;
+      }
     }
     .setting-controls {
       float: left;
diff --git a/app/controllers/admin/site_settings_controller.rb b/app/controllers/admin/site_settings_controller.rb
index 4075f45545b..d12405ff051 100644
--- a/app/controllers/admin/site_settings_controller.rb
+++ b/app/controllers/admin/site_settings_controller.rb
@@ -13,6 +13,11 @@ class Admin::SiteSettingsController < Admin::AdminController
     value = params[id]
     value.strip! if value.is_a?(String)
     raise_access_hidden_setting(id)
+
+    if SiteSetting.type_supervisor.get_type(id) == :upload
+      value = Upload.get_from_url(value) || ''
+    end
+
     SiteSetting.set_and_log(id, value, current_user)
     render body: nil
   end
diff --git a/app/controllers/metadata_controller.rb b/app/controllers/metadata_controller.rb
index 6e157cc5961..07a3ac76327 100644
--- a/app/controllers/metadata_controller.rb
+++ b/app/controllers/metadata_controller.rb
@@ -13,10 +13,14 @@ class MetadataController < ApplicationController
   private
 
   def default_manifest
-    logo = SiteSetting.large_icon_url.presence || SiteSetting.logo_small_url.presence || SiteSetting.apple_touch_icon_url.presence
+    logo = SiteSetting.site_large_icon_url.presence ||
+      SiteSetting.site_logo_small_url.presence ||
+      SiteSetting.site_apple_touch_icon_url.presence
+
     if !logo
-      logo = path('/images/d-logo-sketch-small.png')
+      logo = '/images/d-logo-sketch-small.png'
     end
+
     file_info = get_file_info(logo)
 
     display = Regexp.new(SiteSetting.pwa_display_browser_regex).match(request.user_agent) ? 'browser' : 'standalone'
@@ -30,7 +34,7 @@ class MetadataController < ApplicationController
       theme_color: "##{ColorScheme.hex_for_name('header_background', view_context.scheme_id)}",
       icons: [
         {
-          src: logo,
+          src: UrlHelper.absolute(logo),
           sizes: file_info[:size],
           type: file_info[:type]
         }
diff --git a/app/controllers/site_controller.rb b/app/controllers/site_controller.rb
index 298001e273b..42d1ffe984e 100644
--- a/app/controllers/site_controller.rb
+++ b/app/controllers/site_controller.rb
@@ -37,16 +37,19 @@ class SiteController < ApplicationController
 
   def basic_info
     results = {
-      logo_url: UrlHelper.absolute(SiteSetting.logo_url),
-      logo_small_url: UrlHelper.absolute(SiteSetting.logo_small_url),
-      apple_touch_icon_url: UrlHelper.absolute(SiteSetting.apple_touch_icon_url),
-      favicon_url:  UrlHelper.absolute(SiteSetting.favicon_url),
+      logo_url: UrlHelper.absolute(SiteSetting.site_logo_url),
+      logo_small_url: UrlHelper.absolute(SiteSetting.site_logo_small_url),
+      apple_touch_icon_url: UrlHelper.absolute(SiteSetting.site_apple_touch_icon_url),
+      favicon_url:  UrlHelper.absolute(SiteSetting.site_favicon_url),
       title: SiteSetting.title,
       description: SiteSetting.site_description,
       header_primary_color: ColorScheme.hex_for_name('header_primary') || '333333',
       header_background_color: ColorScheme.hex_for_name('header_background') || 'ffffff'
     }
-    results[:mobile_logo_url] = SiteSetting.mobile_logo_url.presence
+
+    if mobile_logo_url = SiteSetting.site_mobile_logo_url.presence
+      results[:mobile_logo_url] = UrlHelper.absolute(mobile_logo_url)
+    end
 
     DiscourseHub.stats_fetched_at = Time.zone.now if request.user_agent == "Discourse Hub"
 
diff --git a/app/controllers/static_controller.rb b/app/controllers/static_controller.rb
index 5b444fdc87e..c6252dfb784 100644
--- a/app/controllers/static_controller.rb
+++ b/app/controllers/static_controller.rb
@@ -108,10 +108,10 @@ class StaticController < ApplicationController
     is_asset_path
 
     hijack do
-      data = DistributedMemoizer.memoize(FAVICON + SiteSetting.favicon_url, 60 * 30) do
+      data = DistributedMemoizer.memoize(FAVICON + SiteSetting.site_favicon_url, 60 * 30) do
         begin
           file = FileHelper.download(
-            SiteSetting.favicon_url,
+            UrlHelper.absolute(SiteSetting.site_favicon_url),
             max_file_size: 50.kilobytes,
             tmp_file_name: FAVICON,
             follow_redirect: true
@@ -122,7 +122,7 @@ class StaticController < ApplicationController
           data
         rescue => e
           AdminDashboardData.add_problem_message('dashboard.bad_favicon_url', 1800)
-          Rails.logger.debug("Invalid favicon_url #{SiteSetting.favicon_url}: #{e}\n#{e.backtrace}")
+          Rails.logger.debug("Invalid favicon_url #{SiteSetting.site_favicon_url}: #{e}\n#{e.backtrace}")
           ""
         end
       end
diff --git a/app/controllers/uploads_controller.rb b/app/controllers/uploads_controller.rb
index 922e4767e33..b04b393cc56 100644
--- a/app/controllers/uploads_controller.rb
+++ b/app/controllers/uploads_controller.rb
@@ -21,6 +21,7 @@ class UploadsController < ApplicationController
     file   = params[:file] || params[:files]&.first
     pasted = params[:pasted] == "true"
     for_private_message = params[:for_private_message] == "true"
+    for_site_setting = params[:for_site_setting] == "true"
     is_api = is_api?
     retain_hours = params[:retain_hours].to_i
 
@@ -34,6 +35,7 @@ class UploadsController < ApplicationController
           url: url,
           type: type,
           for_private_message: for_private_message,
+          for_site_setting: for_site_setting,
           pasted: pasted,
           is_api: is_api,
           retain_hours: retain_hours
@@ -93,7 +95,16 @@ class UploadsController < ApplicationController
     serialized ||= (data || {}).as_json
   end
 
-  def self.create_upload(current_user:, file:, url:, type:, for_private_message:, pasted:, is_api:, retain_hours:)
+  def self.create_upload(current_user:,
+                         file:,
+                         url:,
+                         type:,
+                         for_private_message:,
+                         for_site_setting:,
+                         pasted:,
+                         is_api:,
+                         retain_hours:)
+
     if file.nil?
       if url.present? && is_api
         maximum_upload_size = [SiteSetting.max_image_size_kb, SiteSetting.max_attachment_size_kb].max.kilobytes
@@ -114,6 +125,7 @@ class UploadsController < ApplicationController
     opts = {
       type: type,
       for_private_message: for_private_message,
+      for_site_setting: for_site_setting,
       pasted: pasted,
     }
 
diff --git a/app/helpers/application_helper.rb b/app/helpers/application_helper.rb
index 5a6998c6e3f..38893536a11 100644
--- a/app/helpers/application_helper.rb
+++ b/app/helpers/application_helper.rb
@@ -192,11 +192,16 @@ module ApplicationHelper
     opts ||= {}
     opts[:url] ||= "#{Discourse.base_url_no_prefix}#{request.fullpath}"
 
-    if opts[:image].blank? && (SiteSetting.default_opengraph_image_url.present? || SiteSetting.twitter_summary_large_image_url.present?)
-      opts[:twitter_summary_large_image] = SiteSetting.twitter_summary_large_image_url if SiteSetting.twitter_summary_large_image_url.present?
-      opts[:image] = SiteSetting.default_opengraph_image_url.present? ? SiteSetting.default_opengraph_image_url : SiteSetting.twitter_summary_large_image_url
-    elsif opts[:image].blank? && SiteSetting.apple_touch_icon_url.present?
-      opts[:image] = SiteSetting.apple_touch_icon_url
+    twitter_summary_large_image_url =
+      SiteSetting.site_twitter_summary_large_image_url
+
+    opengraph_image_url = SiteSetting.opengraph_image_url
+
+    if opts[:image].blank? && (opengraph_image_url.present? || twitter_summary_large_image_url.present?)
+      opts[:twitter_summary_large_image] = twitter_summary_large_image_url if twitter_summary_large_image_url.present?
+      opts[:image] = opengraph_image_url.present? ? opengraph_image_url : twitter_summary_large_image_url
+    elsif opts[:image].blank? && SiteSetting.site_apple_touch_icon_url.present?
+      opts[:image] = SiteSetting.site_apple_touch_icon_url
     end
 
     # Use the correct scheme for open graph image
@@ -271,7 +276,7 @@ module ApplicationHelper
   end
 
   def application_logo_url
-    @application_logo_url ||= (mobile_view? && SiteSetting.mobile_logo_url).presence || SiteSetting.logo_url
+    @application_logo_url ||= (mobile_view? && SiteSetting.site_mobile_logo_url).presence || SiteSetting.site_logo_url
   end
 
   def login_path
diff --git a/app/helpers/user_notifications_helper.rb b/app/helpers/user_notifications_helper.rb
index fbf647be5c8..5d9c98a1936 100644
--- a/app/helpers/user_notifications_helper.rb
+++ b/app/helpers/user_notifications_helper.rb
@@ -18,13 +18,14 @@ module UserNotificationsHelper
   end
 
   def logo_url
-    logo_url = SiteSetting.digest_logo_url
-    logo_url = SiteSetting.logo_url if logo_url.blank? || logo_url =~ /\.svg$/i
-
+    logo_url = SiteSetting.site_digest_logo_url
+    logo_url = SiteSetting.site_logo_url if logo_url.blank? || logo_url =~ /\.svg$/i
     return nil if logo_url.blank? || logo_url =~ /\.svg$/i
+
     if logo_url !~ /http(s)?\:\/\//
       logo_url = "#{Discourse.base_url}#{logo_url}"
     end
+
     logo_url
   end
 
diff --git a/app/jobs/scheduled/clean_up_uploads.rb b/app/jobs/scheduled/clean_up_uploads.rb
index 9f5aed5e7d4..92ec65d165f 100644
--- a/app/jobs/scheduled/clean_up_uploads.rb
+++ b/app/jobs/scheduled/clean_up_uploads.rb
@@ -46,6 +46,11 @@ module Jobs
 
       result = Upload.where("uploads.retain_hours IS NULL OR uploads.created_at < current_timestamp - interval '1 hour' * uploads.retain_hours")
         .where("uploads.created_at < ?", grace_period.hour.ago)
+        .joins(<<~SQL)
+          LEFT JOIN site_settings ss
+          ON ss.value::integer = uploads.id
+          AND ss.data_type = #{SiteSettings::TypeSupervisor.types[:upload].to_i}
+        SQL
         .joins("LEFT JOIN post_uploads pu ON pu.upload_id = uploads.id")
         .joins("LEFT JOIN users u ON u.uploaded_avatar_id = uploads.id")
         .joins("LEFT JOIN user_avatars ua ON ua.gravatar_upload_id = uploads.id OR ua.custom_upload_id = uploads.id")
@@ -62,6 +67,7 @@ module Jobs
         .where("ce.upload_id IS NULL")
         .where("tf.upload_id IS NULL")
         .where("ue.upload_id IS NULL")
+        .where("ss.value IS NULL")
 
       result = result.where("uploads.url NOT IN (?)", ignore_urls) if ignore_urls.present?
 
diff --git a/app/models/site_setting.rb b/app/models/site_setting.rb
index f5b4e9f9f66..b5ef271ba5d 100644
--- a/app/models/site_setting.rb
+++ b/app/models/site_setting.rb
@@ -168,6 +168,55 @@ class SiteSetting < ActiveRecord::Base
     SiteSetting::Upload
   end
 
+  %i{
+    site_logo_url
+    site_logo_small_url
+    site_mobile_logo_url
+    site_favicon_url
+  }.each { |client_setting| client_settings << client_setting }
+
+  def self.site_logo_url
+    self.logo&.url || self.logo_url
+  end
+
+  def self.site_logo_small_url
+    self.logo_small&.url || self.logo_small_url
+  end
+
+  def self.site_digest_logo_url
+    self.digest_logo&.url || self.digest_logo_url
+  end
+
+  def self.site_mobile_logo_url
+    self.mobile_logo&.url || self.mobile_logo_url
+  end
+
+  def self.site_large_icon_url
+    self.large_icon&.url || self.large_icon_url
+  end
+
+  def self.site_favicon_url
+    self.favicon&.url || self.favicon_url
+  end
+
+  def self.site_apple_touch_icon_url
+    self.apple_touch_icon&.url || self.apple_touch_icon_url
+  end
+
+  def self.opengraph_image_url
+    self.opengraph_image&.url || self.default_opengraph_image_url
+  end
+
+  def self.site_twitter_summary_large_image_url
+    self.twitter_summary_large_image&.url ||
+      self.twitter_summary_large_image_url
+  end
+
+  def self.site_push_notifications_icon_url
+    SiteSetting.push_notifications_icon&.url ||
+      SiteSetting.push_notifications_icon_url
+  end
+
   def self.shared_drafts_enabled?
     c = SiteSetting.shared_drafts_category
     c.present? && c.to_i != SiteSetting.uncategorized_category_id.to_i
diff --git a/app/models/upload.rb b/app/models/upload.rb
index 9e50a49b36d..bf3d4155154 100644
--- a/app/models/upload.rb
+++ b/app/models/upload.rb
@@ -21,6 +21,7 @@ class Upload < ActiveRecord::Base
   attr_accessor :for_theme
   attr_accessor :for_private_message
   attr_accessor :for_export
+  attr_accessor :for_site_setting
 
   validates_presence_of :filesize
   validates_presence_of :original_filename
@@ -33,6 +34,10 @@ class Upload < ActiveRecord::Base
     UserAvatar.where(custom_upload_id: self.id).update_all(custom_upload_id: nil)
   end
 
+  def to_s
+    self.url
+  end
+
   def thumbnail(width = self.thumbnail_width, height = self.thumbnail_height)
     optimized_images.find_by(width: width, height: height)
   end
diff --git a/app/services/push_notification_pusher.rb b/app/services/push_notification_pusher.rb
index 204e3f668be..2e39eb9cac9 100644
--- a/app/services/push_notification_pusher.rb
+++ b/app/services/push_notification_pusher.rb
@@ -65,9 +65,11 @@ class PushNotificationPusher
   protected
 
   def self.get_badge
-    return !SiteSetting.push_notifications_icon_url.blank? ?
-             SiteSetting.push_notifications_icon_url :
-             ActionController::Base.helpers.image_url("push-notifications/discourse.png")
+    if SiteSetting.site_push_notifications_icon_url.present?
+      SiteSetting.site_push_notifications_icon_url
+    else
+      ActionController::Base.helpers.image_url("push-notifications/discourse.png")
+    end
   end
 
   def self.send_notification(user, subscription, message)
diff --git a/app/views/embed/comments.html.erb b/app/views/embed/comments.html.erb
index 25735bfc4a9..59d38298cf7 100644
--- a/app/views/embed/comments.html.erb
+++ b/app/views/embed/comments.html.erb
@@ -40,7 +40,7 @@
 
   <% if @topic_view.topic.posts_count > 0 %>
     <footer class="clearfix">
-      <%= link_to(image_tag(SiteSetting.logo_url, class: 'logo'), Discourse.base_url, target: '_blank') %>
+      <%= link_to(image_tag(SiteSetting.site_logo_url, class: 'logo'), Discourse.base_url, target: '_blank') %>
       <%= link_to(I18n.t('embed.continue'), @topic_view.posts.last.full_url, class: 'button', target: '_blank') %>
       <%- if @posts_left > 0 %>
         <span class='replies'><%= I18n.t('embed.more_replies', count: @posts_left) %></span>
diff --git a/app/views/embed/embed_error.html.erb b/app/views/embed/embed_error.html.erb
index b6b1121b80c..37403f69b1c 100644
--- a/app/views/embed/embed_error.html.erb
+++ b/app/views/embed/embed_error.html.erb
@@ -1,6 +1,6 @@
 <header class='discourse' data-embed-state='error'>
   <h3><%= t 'embed.error' %></h3>
-  <%= link_to(image_tag(SiteSetting.logo_url, class: 'logo'), Discourse.base_url) %>
+  <%= link_to(image_tag(SiteSetting.site_logo_url, class: 'logo'), Discourse.base_url) %>
   <div class='clearfix'></div>
 </header>
 <%- if @show_reason %>
diff --git a/app/views/embed/loading.html.erb b/app/views/embed/loading.html.erb
index ccb68dbdf46..f2ecf83e51d 100644
--- a/app/views/embed/loading.html.erb
+++ b/app/views/embed/loading.html.erb
@@ -1,6 +1,6 @@
 <header class='discourse' data-embed-state='loading'>
   <h3><%= t 'embed.loading' %></h3>
-  <%= link_to(image_tag(SiteSetting.logo_url, class: 'logo'), Discourse.base_url) %>
+  <%= link_to(image_tag(SiteSetting.site_logo_url, class: 'logo'), Discourse.base_url) %>
   <div class='clearfix'></div>
 </header>
 <script>
diff --git a/app/views/layouts/_head.html.erb b/app/views/layouts/_head.html.erb
index 0b3039868ef..898ffd7f4b3 100644
--- a/app/views/layouts/_head.html.erb
+++ b/app/views/layouts/_head.html.erb
@@ -1,13 +1,14 @@
 <meta name="author" content="">
 <meta name="generator" content="Discourse <%= Discourse::VERSION::STRING %> - https://github.com/discourse/discourse version <%= Discourse.git_version %>">
-<%- if SiteSetting.favicon_url.present? %>
-<link rel="icon" type="image/png" href="<%=SiteSetting.favicon_url%>">
+<%- if SiteSetting.site_favicon_url.present? %>
+<link rel="icon" type="image/png" href="<%=SiteSetting.site_favicon_url%>">
 <%- end %>
-<%- if SiteSetting.apple_touch_icon_url.present? %>
-<link rel="apple-touch-icon" type="image/png" href="<%=SiteSetting.apple_touch_icon_url%>">
+<% site_apple_touch_icon_url = SiteSetting.site_apple_touch_icon_url %>
+<%- if site_apple_touch_icon_url.present? %>
+<link rel="apple-touch-icon" type="image/png" href="<%= site_apple_touch_icon_url %>">
 <%- end %>
-<%- if (SiteSetting.apple_touch_icon_url != "/images/default-apple-touch-icon.png") && SiteSetting.apple_touch_icon_url.present? %>
-<link rel="icon" type="image/png" sizes="144x144" href="<%=SiteSetting.apple_touch_icon_url%>">
+<%- if (site_apple_touch_icon_url != "/images/default-apple-touch-icon.png") && site_apple_touch_icon_url.present? %>
+<link rel="icon" type="image/png" sizes="144x144" href="<%= site_apple_touch_icon_url %>">
 <%- end %>
 <meta name="theme-color" content="#<%= ColorScheme.hex_for_name('header_background', scheme_id) %>">
 <% if mobile_view? %>
diff --git a/app/views/layouts/crawler.html.erb b/app/views/layouts/crawler.html.erb
index 914de1f1b0d..f8c4aae8e2e 100644
--- a/app/views/layouts/crawler.html.erb
+++ b/app/views/layouts/crawler.html.erb
@@ -23,8 +23,8 @@
     <%= theme_lookup("header") %>
     <header>
       <a href="<%= path "/" %>">
-        <%- if SiteSetting.logo_url.present? %>
-          <img src="<%=SiteSetting.logo_url%>" alt="<%=SiteSetting.title%>" id="site-logo" style="max-width: 150px;">
+        <%- if SiteSetting.site_logo_url.present? %>
+          <img src="<%=SiteSetting.site_logo_url%>" alt="<%=SiteSetting.title%>" id="site-logo" style="max-width: 150px;">
         <%- else %>
           <h1><%=SiteSetting.title%></h1>
         <% end %>
diff --git a/app/views/metadata/opensearch.xml.erb b/app/views/metadata/opensearch.xml.erb
index 4e237c65e98..5495c3ffc9d 100644
--- a/app/views/metadata/opensearch.xml.erb
+++ b/app/views/metadata/opensearch.xml.erb
@@ -3,10 +3,12 @@
   <ShortName><%= SiteSetting.title %> Search</ShortName>
   <Description>Search for posts on <%= SiteSetting.title %></Description>
   <Tags>discourse forum</Tags>
-  <% if SiteSetting.favicon_url =~ /\.ico$/ -%>
-  <Image height="16" width="16" type="image/vnd.microsoft.icon"><%= UrlHelper.absolute SiteSetting.favicon_url %></Image>
+  <% site_favicon_url = SiteSetting.site_favicon_url %>
+  <% absolute_site_favicon_url = UrlHelper.absolute(site_favicon_url) %>
+  <% if site_favicon_url =~ /\.ico$/ -%>
+    <Image height="16" width="16" type="image/vnd.microsoft.icon"><%= absolute_site_favicon_url %></Image>
   <%- else -%>
-  <Image type="image/png"><%= UrlHelper.absolute SiteSetting.favicon_url %></Image>
+    <Image type="image/png"><%= absolute_site_favicon_url %></Image>
   <%- end %>
   <Url type="application/opensearchdescription+xml" rel="self" template="<%= Discourse.base_url %>/opensearch.xml"/>
   <Url type="text/html" template="<%= Discourse.base_url %>/search?q={searchTerms}"/>
diff --git a/config/locales/server.en.yml b/config/locales/server.en.yml
index c21e5afacab..80db8ed306d 100644
--- a/config/locales/server.en.yml
+++ b/config/locales/server.en.yml
@@ -1146,7 +1146,7 @@ en:
       one: "Email polling has generated an error in the past 24 hours. Look at <a href='%{base_path}/logs' target='_blank'>the logs</a> for more details."
       other: "Email polling has generated %{count} errors in the past 24 hours. Look at <a href='%{base_path}/logs' target='_blank'>the logs</a> for more details."
     missing_mailgun_api_key: "The server is configured to send emails via Mailgun but you haven't provided an API key used to verify the webhook messages."
-    bad_favicon_url: "The favicon is failing to load. Check your favicon_url setting in <a href='%{base_path}/admin/site_settings'>Site Settings</a>."
+    bad_favicon_url: "The favicon is failing to load. Check your favicon setting in <a href='%{base_path}/admin/site_settings'>Site Settings</a>."
     poll_pop3_timeout: "Connection to the POP3 server is timing out. Incoming email could not be retrieved. Please check your <a href='%{base_path}/admin/site_settings/category/email'>POP3 settings</a> and service provider."
     poll_pop3_auth_error: "Connection to the POP3 server is failing with an authentication error. Please check your <a href='%{base_path}/admin/site_settings/category/email'>POP3 settings</a>."
     force_https_warning: "Your website is using SSL. But `<a href='%{base_path}/admin/site_settings/category/all_results?filter=force_https'>force_https</a>` is not yet enabled in your site settings."
@@ -1215,13 +1215,15 @@ en:
     enable_inline_onebox_on_all_domains: "Ignore inline_onebox_domain_whitelist site setting and allow inline onebox on all domains."
     max_oneboxes_per_post: "Maximum number of oneboxes in a post."
 
-    logo_url: "The logo image at the top left of your site, should be a wide rectangle shape. If left blank site title text will be shown. Use <a href='%{base_path}/wizard/steps/logos' target='_blank'>the wizard</a> to update."
-    digest_logo_url: "The alternate logo image used at the top of your site's email summary. Should be a wide rectangle shape. Should not be an SVG image. If left blank `logo_url` will be used."
-    logo_small_url: "The small logo image at the top left of your site, should be a square shape, seen when scrolling down. If left blank a home glyph will be shown. Use <a href='%{base_path}/wizard/steps/logos' target='_blank'>the wizard</a> to update."
-    favicon_url: "A favicon for your site, see <a href='https://en.wikipedia.org/wiki/Favicon' target='_blank'>https://en.wikipedia.org/wiki/Favicon</a>. To work correctly over a CDN it must be a png. Use <a href='%{base_path}/wizard/steps/icons' target='_blank'>the wizard</a> to update."
-    mobile_logo_url: "Custom logo url used on mobile version of your site. If left blank, `logo_url` will be used. eg: https://example.com/uploads/default/logo.png"
-    large_icon_url: "Image used as logo/splash image on Android. Recommended size is 512px by 512px. Use <a href='%{base_path}/wizard/steps/icons' target='_blank'>the wizard</a> to update."
-    apple_touch_icon_url: "Icon used for Apple touch devices. Recommended size is 144px by 144px."
+    logo: "The logo image at the top left of your site, should be a wide rectangle shape. If left blank site title text will be shown."
+    logo_small: "The small logo image at the top left of your site, should be a square shape, seen when scrolling down. If left blank a home glyph will be shown."
+    digest_logo: "The alternate logo image used at the top of your site's email summary. Should be a wide rectangle shape. Should not be an SVG image. If left blank `logo_url` will be used."
+    mobile_logo: "Custom logo url used on mobile version of your site. If left blank, `logo_url` will be used. eg: https://example.com/uploads/default/logo.png"
+    large_icon: "Image used as logo/splash image on Android. Recommended size is 512px by 512px."
+    favicon: "A favicon for your site, see <a href='https://en.wikipedia.org/wiki/Favicon' target='_blank'>https://en.wikipedia.org/wiki/Favicon</a>. To work correctly over a CDN it must be a png."
+    apple_touch_icon: "Icon used for Apple touch devices. Recommended size is 144px by 144px."
+    opengraph_image: "Default opengraph image, used when the page has no other suitable image or site logo."
+    twitter_summary_large_image: "Default Twitter summary card image (should be at least 280px in width, and at least 150px in height)."
 
     notification_email: "The from: email address used when sending all essential system emails. The domain specified here must have SPF, DKIM and reverse PTR records set correctly for email to arrive."
     email_custom_headers: "A pipe-delimited list of custom email headers"
@@ -1454,9 +1456,6 @@ en:
     selectable_avatars_enabled: "Force users to choose an avatar from the list."
     selectable_avatars: "List of avatars users can choose from."
 
-    default_opengraph_image_url: "Default opengraph image, used when the page has no other suitable image or site logo."
-    twitter_summary_large_image_url: "Default Twitter summary card image (should be at least 280px in width, and at least 150px in height)."
-
     allow_all_attachments_for_group_messages: "Allow all email attachments for group messages."
 
     png_to_jpg_quality: "Quality of the converted JPG file (1 is lowest quality, 99 is best quality, 100 to disable)."
@@ -1850,7 +1849,7 @@ en:
     shared_drafts_category: "Enable the Shared Drafts feature by designating a category for topic drafts. Topics in this category will be suppressed from topic lists for staff users."
 
     push_notifications_prompt: "Display user consent prompt."
-    push_notifications_icon_url: "The badge icon that appears in the notification corner. Recommended size is 96px by 96px."
+    push_notifications_icon: "The badge icon that appears in the notification corner. Recommended size is 96px by 96px."
 
     errors:
       invalid_email: "Invalid email address."
@@ -4067,20 +4066,20 @@ en:
       logos:
         title: "Logos"
         fields:
-          logo_url:
+          logo:
             label: "Primary Logo"
             description: "The logo image at the top left of your site. Use a wide rectangle shape."
-          logo_small_url:
+          logo_small:
             label: "Compact Logo"
             description: "A compact version of your logo, shown at the top left of your site when scrolling down. Use a square shape."
 
       icons:
         title: "Icons"
         fields:
-          favicon_url:
+          favicon:
             label: "Small Icon"
             description: "Icon image used to represent your site in web browsers that looks good at small sizes such as 32px by 32px. Recommended image extensions are PNG or JPG."
-          apple_touch_icon_url:
+          apple_touch_icon:
             label: "Large Icon"
             description: "Icon image used to represent your site on modern devices that looks good at larger sizes. Recommended size is at least 512px by 512px."
 
diff --git a/config/site_settings.yml b/config/site_settings.yml
index 3c5e32d4610..2c134a29282 100644
--- a/config/site_settings.yml
+++ b/config/site_settings.yml
@@ -45,25 +45,67 @@ required:
   site_contact_username:
     default: ''
     type: username
+  logo:
+    default: ''
+    client: true
+    type: upload
   logo_url:
-    client: true
+    hidden: true
     default: '/images/d-logo-sketch.png'
+  logo_small:
+    default: ''
+    client: true
+    type: upload
   logo_small_url:
-    client: true
+    hidden: true
     default: '/images/d-logo-sketch-small.png'
+  digest_logo:
+    default: ''
+    client: true
+    type: upload
   digest_logo_url:
+    hidden: true
     default: ''
+  mobile_logo:
+    default: ''
+    client: true
+    type: upload
   mobile_logo_url:
-    client: true
+    hidden: true
     default: ''
+  large_icon:
+    default: ''
+    client: true
+    type: upload
   large_icon_url:
+    hidden: true
+    default: ''
+  favicon:
     default: ''
-  favicon_url:
     client: true
+    type: upload
+  favicon_url:
+    hidden: true
     default: '/images/default-favicon.ico'
-  apple_touch_icon_url: '/images/default-apple-touch-icon.png'
-  default_opengraph_image_url: ''
-  twitter_summary_large_image_url: ''
+  apple_touch_icon:
+    default: ''
+    client: true
+    type: upload
+  apple_touch_icon_url:
+    hidden: true
+    default: '/images/default-apple-touch-icon.png'
+  opengraph_image:
+    default: ''
+    type: upload
+  default_opengraph_image_url:
+    hidden: true
+    default: ''
+  twitter_summary_large_image:
+    default: ''
+    type: upload
+  twitter_summary_large_image_url:
+    hidden: true
+    default: ''
   exclude_rel_nofollow_domains:
     default: ''
     type: list
@@ -233,7 +275,11 @@ basic:
   push_notifications_prompt:
     default: true
     client: true
+  push_notifications_icon:
+    default: ''
+    type: upload
   push_notifications_icon_url:
+    hidden: true
     default: ''
   vapid_public_key_bytes:
     default: ''
diff --git a/db/post_migrate/20181112013117_migrate_url_site_settings.rb b/db/post_migrate/20181112013117_migrate_url_site_settings.rb
new file mode 100644
index 00000000000..369d46d9afa
--- /dev/null
+++ b/db/post_migrate/20181112013117_migrate_url_site_settings.rb
@@ -0,0 +1,75 @@
+class MigrateUrlSiteSettings < ActiveRecord::Migration[5.2]
+  def up
+    [
+      ['logo_url', 'logo'],
+      ['logo_small_url', 'logo_small'],
+      ['digest_logo_url', 'digest_logo'],
+      ['mobile_logo_url', 'mobile_logo'],
+      ['large_icon_url', 'large_icon'],
+      ['favicon_url', 'favicon'],
+      ['apple_touch_icon_url', 'apple_touch_icon'],
+      ['default_opengraph_image_url', 'opengraph_image'],
+      ['twitter_summary_large_image_url', 'twitter_summary_large_image'],
+      ['push_notifications_icon_url', 'push_notifications_icon'],
+    ].each do |old_setting, new_setting|
+      old_url = DB.query_single(
+        "SELECT value FROM site_settings WHERE name = '#{old_setting}'"
+      ).first
+
+      next if old_url.blank?
+
+      count = 0
+      file = nil
+      sleep_interval = 5
+
+      loop do
+        url = UrlHelper.absolute(old_url)
+
+        begin
+          file = FileHelper.download(
+            url,
+            max_file_size: 20.megabytes,
+            tmp_file_name: 'tmp_site_setting_logo',
+            skip_rate_limit: true,
+            follow_redirect: true
+          )
+        rescue OpenURI::HTTPError => e
+          logger.info(
+            "HTTP error encountered when trying to download file " +
+            "for #{new_setting}.\n#{e.message}"
+          )
+        end
+
+        count += 1
+        break if file || (file.blank? && count >= 3)
+
+        logger.info(
+          "Failed to download upload from #{url} for #{new_setting}. Retrying..."
+        )
+
+        sleep(count * sleep_interval)
+      end
+
+      next if file.blank?
+
+      upload = UploadCreator.new(
+        file,
+        "#{new_setting}",
+        origin: UrlHelper.absolute(old_url),
+        for_site_setting: true
+      ).create_for(Discourse.system_user.id)
+
+      SiteSetting.public_send("#{new_setting}=", upload)
+    end
+  end
+
+  def down
+    raise ActiveRecord::IrreversibleMigration
+  end
+
+  private
+
+  def logger
+    Rails.logger
+  end
+end
diff --git a/lib/site_setting_extension.rb b/lib/site_setting_extension.rb
index b556584a0d7..22cd16adeb5 100644
--- a/lib/site_setting_extension.rb
+++ b/lib/site_setting_extension.rb
@@ -190,7 +190,11 @@ module SiteSettingExtension
   end
 
   def client_settings_json_uncached
-    MultiJson.dump(Hash[*@client_settings.map { |n| [n, self.send(n)] }.flatten])
+    MultiJson.dump(Hash[*@client_settings.map do |name|
+      value = self.public_send(name)
+      value = value.to_s if type_supervisor.get_type(name) == :upload
+      [name, value]
+    end.flatten])
   end
 
   # Retrieve all settings
@@ -212,7 +216,9 @@ module SiteSettingExtension
     defaults.all(default_locale)
       .reject { |s, _| !include_hidden && hidden_settings.include?(s) }
       .map do |s, v|
+
       value = send(s)
+
       opts = {
         setting: s,
         description: description(s),
@@ -312,6 +318,7 @@ module SiteSettingExtension
   def remove_override!(name)
     provider.destroy(name)
     current[name] = defaults.get(name, default_locale)
+    uploads.delete(name)
     clear_cache!
   end
 
@@ -319,6 +326,7 @@ module SiteSettingExtension
     val, type = type_supervisor.to_db_value(name, val)
     provider.save(name, val, type)
     current[name] = type_supervisor.to_rb_value(name, val)
+    uploads.delete(name)
     notify_clients!(name) if client_settings.include? name
     clear_cache!
   end
@@ -410,12 +418,31 @@ module SiteSettingExtension
   def setup_methods(name)
     clean_name = name.to_s.sub("?", "").to_sym
 
-    define_singleton_method clean_name do
-      if (c = current[name]).nil?
-        refresh!
-        current[name]
-      else
-        c
+    if type_supervisor.get_type(name) == :upload
+      define_singleton_method clean_name do
+        upload = uploads[name]
+        return upload if upload
+
+        if (value = current[name]).nil?
+          refresh!
+          value = current[name]
+        end
+
+        value = value.to_i
+
+        if value > 0
+          upload = Upload.find_by(id: value)
+          uploads[name] = upload if upload
+        end
+      end
+    else
+      define_singleton_method clean_name do
+        if (c = current[name]).nil?
+          refresh!
+          current[name]
+        else
+          c
+        end
       end
     end
 
@@ -448,6 +475,11 @@ module SiteSettingExtension
 
   private
 
+  def uploads
+    @uploads ||= {}
+    @uploads[provider.current_site] ||= {}
+  end
+
   def logger
     Rails.logger
   end
diff --git a/lib/site_settings/type_supervisor.rb b/lib/site_settings/type_supervisor.rb
index 32fd7733751..0f4f483faaa 100644
--- a/lib/site_settings/type_supervisor.rb
+++ b/lib/site_settings/type_supervisor.rb
@@ -31,6 +31,7 @@ class SiteSettings::TypeSupervisor
       username: 15,
       category: 16,
       uploaded_image_list: 17,
+      upload: 18,
     )
   end
 
@@ -133,7 +134,7 @@ class SiteSettings::TypeSupervisor
 
   def type_hash(name)
     name = name.to_sym
-    type = self.class.types[@types[name]]
+    type = get_type(name)
 
     result = { type: type.to_s }
 
@@ -150,6 +151,10 @@ class SiteSettings::TypeSupervisor
     result
   end
 
+  def get_type(name)
+    self.class.types[@types[name.to_sym]]
+  end
+
   private
 
   def normalize_input(name, val)
@@ -164,6 +169,8 @@ class SiteSettings::TypeSupervisor
       type = get_data_type(name, val)
     elsif type == self.class.types[:enum]
       val = @defaults_provider[name].is_a?(Integer) ? val.to_i : val.to_s
+    elsif type == self.class.types[:upload] && val.present?
+      val = val.id
     end
 
     [val, type]
diff --git a/lib/site_settings/yaml_loader.rb b/lib/site_settings/yaml_loader.rb
index 82e9d851be4..c9352664dbc 100644
--- a/lib/site_settings/yaml_loader.rb
+++ b/lib/site_settings/yaml_loader.rb
@@ -12,6 +12,7 @@ class SiteSettings::YamlLoader
         if hash.is_a?(Hash)
           # Get default value for the site setting:
           value = hash.delete('default')
+
           if value.is_a?(Hash)
             raise Discourse::Deprecation, "The site setting `#{setting_name}` can no longer be set based on Rails environment. See also `config/environments/<env>.rb`."
           elsif value.nil?
diff --git a/lib/upload_creator.rb b/lib/upload_creator.rb
index 431f4f6b94a..33a6704cd4b 100644
--- a/lib/upload_creator.rb
+++ b/lib/upload_creator.rb
@@ -117,6 +117,7 @@ class UploadCreator
       @upload.for_group_message   = true if @opts[:for_group_message]
       @upload.for_theme           = true if @opts[:for_theme]
       @upload.for_export          = true if @opts[:for_export]
+      @upload.for_site_setting    = true if @opts[:for_site_setting]
 
       return @upload unless @upload.save
 
diff --git a/lib/validators/upload_validator.rb b/lib/validators/upload_validator.rb
index b546ebf1554..d69bd6cb01c 100644
--- a/lib/validators/upload_validator.rb
+++ b/lib/validators/upload_validator.rb
@@ -6,7 +6,7 @@ class Validators::UploadValidator < ActiveModel::Validator
 
   def validate(upload)
     # staff can upload any file in PM
-    if upload.for_private_message && SiteSetting.allow_staff_to_upload_any_file_in_pm
+    if (upload.for_private_message && SiteSetting.allow_staff_to_upload_any_file_in_pm)
       return true if upload.user&.staff?
     end
 
@@ -17,6 +17,13 @@ class Validators::UploadValidator < ActiveModel::Validator
 
     extension = File.extname(upload.original_filename)[1..-1] || ""
 
+    if upload.for_site_setting &&
+       upload.user&.staff? &&
+       FileHelper.is_supported_image?(upload.original_filename)
+
+      return true
+    end
+
     if is_authorized?(upload, extension)
       if FileHelper.is_supported_image?(upload.original_filename)
         authorized_image_extension(upload, extension)
diff --git a/lib/wizard/builder.rb b/lib/wizard/builder.rb
index 8c00c2ae1ba..18d198f50c1 100644
--- a/lib/wizard/builder.rb
+++ b/lib/wizard/builder.rb
@@ -144,26 +144,27 @@ class Wizard
       end
 
       @wizard.append_step('logos') do |step|
-        step.add_field(id: 'logo_url', type: 'image', value: SiteSetting.logo_url)
-        step.add_field(id: 'logo_small_url', type: 'image', value: SiteSetting.logo_small_url)
+        step.add_field(id: 'logo', type: 'image', value: SiteSetting.site_logo_url)
+        step.add_field(id: 'logo_small', type: 'image', value: SiteSetting.site_logo_small_url)
 
         step.on_update do |updater|
-          updater.apply_settings(:logo_url, :logo_small_url)
+          updater.apply_settings(:logo, :logo_small)
         end
       end
 
       @wizard.append_step('icons') do |step|
-        step.add_field(id: 'favicon_url', type: 'image', value: SiteSetting.favicon_url)
-        step.add_field(id: 'apple_touch_icon_url', type: 'image', value: SiteSetting.apple_touch_icon_url)
+        step.add_field(id: 'favicon', type: 'image', value: SiteSetting.favicon)
+        step.add_field(id: 'apple_touch_icon', type: 'image', value: SiteSetting.apple_touch_icon)
 
         step.on_update do |updater|
-          updater.apply_settings(:favicon_url)
+          updater.apply_settings(:favicon)
 
-          if updater.fields[:apple_touch_icon_url] != SiteSetting.apple_touch_icon_url
-            upload = Upload.find_by_url(updater.fields[:apple_touch_icon_url])
+          if updater.fields[:apple_touch_icon] != SiteSetting.apple_touch_icon
+            upload = Upload.find_by_url(updater.fields[:apple_touch_icon])
             dimensions = 180 # for apple touch icon
+
             if upload && upload.width > dimensions && upload.height > dimensions
-              updater.update_setting(:large_icon_url, updater.fields[:apple_touch_icon_url])
+              updater.update_setting(:large_icon, upload)
 
               apple_touch_icon_optimized = OptimizedImage.create_for(
                 upload,
@@ -172,13 +173,15 @@ class Wizard
               )
 
               original_file = File.new(Discourse.store.path_for(apple_touch_icon_optimized)) rescue nil
+
               if original_file
                 apple_touch_icon_upload = UploadCreator.new(original_file, upload.original_filename).create_for(@wizard.user.id)
-                updater.update_setting(:apple_touch_icon_url, apple_touch_icon_upload.url)
+                updater.update_setting(:apple_touch_icon, apple_touch_icon_upload)
               end
+
               apple_touch_icon_optimized.destroy! if apple_touch_icon_optimized.present?
             else
-              updater.apply_settings(:apple_touch_icon_url)
+              updater.apply_settings(:apple_touch_icon)
             end
           end
         end
diff --git a/lib/wizard/step_updater.rb b/lib/wizard/step_updater.rb
index 3d8ad87a3d6..5b1c88db7f1 100644
--- a/lib/wizard/step_updater.rb
+++ b/lib/wizard/step_updater.rb
@@ -30,6 +30,11 @@ class Wizard
 
     def update_setting(id, value)
       value.strip! if value.is_a?(String)
+
+      if !value.is_a?(Upload) && SiteSetting.type_supervisor.get_type(id) == :upload
+        value = Upload.get_from_url(value) || ''
+      end
+
       SiteSetting.set_and_log(id, value, @current_user) if SiteSetting.send(id) != value
     end
 
diff --git a/plugins/discourse-narrative-bot/lib/discourse_narrative_bot/certificate_generator.rb b/plugins/discourse-narrative-bot/lib/discourse_narrative_bot/certificate_generator.rb
index 656505dcff7..047e643b002 100644
--- a/plugins/discourse-narrative-bot/lib/discourse_narrative_bot/certificate_generator.rb
+++ b/plugins/discourse-narrative-bot/lib/discourse_narrative_bot/certificate_generator.rb
@@ -568,10 +568,10 @@ module DiscourseNarrativeBot
     end
 
     def logo_group(size, width, height)
-      return unless SiteSetting.logo_small_url.present?
+      return unless SiteSetting.site_logo_small_url.present?
 
       begin
-        uri = URI(SiteSetting.logo_small_url)
+        uri = URI(SiteSetting.site_logo_small_url)
 
         logo_uri =
           if uri.host.blank? || uri.scheme.blank?
diff --git a/plugins/discourse-narrative-bot/spec/lib/certificate_generator_spec.rb b/plugins/discourse-narrative-bot/spec/lib/certificate_generator_spec.rb
index 69f7e5e848d..cc9e37e740b 100644
--- a/plugins/discourse-narrative-bot/spec/lib/certificate_generator_spec.rb
+++ b/plugins/discourse-narrative-bot/spec/lib/certificate_generator_spec.rb
@@ -10,8 +10,9 @@ RSpec.describe DiscourseNarrativeBot::CertificateGenerator do
   end
 
   describe '#logo_group' do
-    describe 'when SiteSetting.logo_small_url is blank' do
+    describe 'when SiteSetting.site_logo_small_url is blank' do
       before do
+        SiteSetting.logo_small = ''
         SiteSetting.logo_small_url = ''
       end
 
diff --git a/spec/components/site_setting_extension_spec.rb b/spec/components/site_setting_extension_spec.rb
index 46e9a71c23b..1b76de978e3 100644
--- a/spec/components/site_setting_extension_spec.rb
+++ b/spec/components/site_setting_extension_spec.rb
@@ -703,4 +703,39 @@ describe SiteSettingExtension do
 
   end
 
+  describe '.client_settings_json_uncached' do
+    it 'should return the right json value' do
+      upload = Fabricate(:upload)
+      settings.setting(:upload_type, upload.id.to_s, type: :upload, client: true)
+      settings.setting(:string_type, 'haha', client: true)
+      settings.refresh!
+
+      expect(settings.client_settings_json_uncached).to eq(
+        %Q|{"default_locale":"en","upload_type":"#{upload.url}","string_type":"haha"}|
+      )
+    end
+  end
+
+  describe '.setup_methods' do
+    describe 'for uploads site settings' do
+      let(:upload) { Fabricate(:upload) }
+      let(:upload2) { Fabricate(:upload) }
+
+      it 'should return the upload record' do
+        settings.setting(:some_upload, upload.id.to_s, type: :upload)
+
+        expect(settings.some_upload).to eq(upload)
+
+        # Ensure that we cache the upload record
+        expect(settings.some_upload.object_id).to eq(
+          settings.some_upload.object_id
+        )
+
+        settings.some_upload = upload2
+
+        expect(settings.some_upload).to eq(upload2)
+      end
+    end
+  end
+
 end
diff --git a/spec/components/site_settings/type_supervisor_spec.rb b/spec/components/site_settings/type_supervisor_spec.rb
index 1683ebf9e89..9aa361c10a6 100644
--- a/spec/components/site_settings/type_supervisor_spec.rb
+++ b/spec/components/site_settings/type_supervisor_spec.rb
@@ -79,6 +79,10 @@ describe SiteSettings::TypeSupervisor do
       it "'uploaded_image_list' should be at 17th position" do
         expect(SiteSettings::TypeSupervisor.types[:uploaded_image_list]).to eq(17)
       end
+
+      it "'upload' should be at the right position" do
+        expect(SiteSettings::TypeSupervisor.types[:upload]).to eq(18)
+      end
     end
   end
 
@@ -151,10 +155,11 @@ describe SiteSettings::TypeSupervisor do
       settings.setting(:type_validator, 5, validator: 'TestSmallThanTenValidator')
       settings.setting(:type_mock_validate_method, 'no_value')
       settings.setting(:type_custom, 'custom', type: 'list')
+      settings.setting(:type_upload, '', type: 'upload')
       settings.refresh!
     end
 
-    describe '.to_db_value' do
+    describe '#to_db_value' do
       let(:true_val) { 't' }
       let(:false_val) { 'f' }
 
@@ -187,6 +192,13 @@ describe SiteSettings::TypeSupervisor do
         expect(settings.type_supervisor.to_db_value(:type_string, 'a')).to eq ['a', SiteSetting.types[:string]]
       end
 
+      it 'returns the upload id' do
+        upload = Fabricate(:upload)
+
+        expect(settings.type_supervisor.to_db_value(:type_upload, upload))
+          .to eq([upload.id, SiteSetting.types[:upload]])
+      end
+
       it 'returns enum value with string default' do
         expect(settings.type_supervisor.to_db_value(:type_enum_default_string, 2)).to eq ['2', SiteSetting.types[:enum]]
         expect(settings.type_supervisor.to_db_value(:type_enum_default_string, '2')).to eq ['2', SiteSetting.types[:enum]]
@@ -224,7 +236,7 @@ describe SiteSettings::TypeSupervisor do
       end
     end
 
-    describe '.to_rb_value' do
+    describe '#to_rb_value' do
       let(:true_val) { 't' }
       let(:false_val) { 'f' }
 
@@ -266,6 +278,16 @@ describe SiteSettings::TypeSupervisor do
         expect(settings.type_supervisor.to_rb_value(:type_string, 2)).to eq '2'
       end
 
+      it 'returns the upload record' do
+        upload = Fabricate(:upload)
+
+        expect(settings.type_supervisor.to_rb_value(:type_upload, ''))
+          .to eq('')
+
+        expect(settings.type_supervisor.to_rb_value(:type_upload, upload.id))
+          .to eq(upload.id)
+      end
+
       it 'returns value with string default' do
         expect(settings.type_supervisor.to_rb_value(:type_enum_default_string, 2)).to eq '2'
         expect(settings.type_supervisor.to_rb_value(:type_enum_default_string, '2')).to eq '2'
@@ -284,6 +306,18 @@ describe SiteSettings::TypeSupervisor do
     end
   end
 
+  describe '#get_type' do
+    before do
+      settings.setting(:type_null, nil)
+      settings.setting(:type_upload, '', type: :upload)
+    end
+
+    it 'should return the right type that has been registered' do
+      expect(settings.type_supervisor.get_type(:type_null)).to eq(:null)
+      expect(settings.type_supervisor.get_type(:type_upload)).to eq(:upload)
+    end
+  end
+
   describe '.type_hash' do
     class TestEnumClass2
       def self.valid_value?(v)
diff --git a/spec/components/validators/upload_validator_spec.rb b/spec/components/validators/upload_validator_spec.rb
index 28d899c66b9..8e9a952ee51 100644
--- a/spec/components/validators/upload_validator_spec.rb
+++ b/spec/components/validators/upload_validator_spec.rb
@@ -53,5 +53,42 @@ describe Validators::UploadValidator do
         end
       end
     end
+
+    describe 'upload for site settings' do
+      let(:user) { Fabricate(:admin) }
+
+      let(:upload) do
+        Fabricate.build(:upload,
+          user: user,
+          original_filename: 'test.ico',
+          for_site_setting: true
+        )
+      end
+
+      before do
+        SiteSetting.authorized_extensions = 'png'
+      end
+
+      describe 'for admin user' do
+        it 'should allow the upload' do
+          expect(subject.validate(upload)).to eq(true)
+        end
+
+        describe 'when filename is invalid' do
+          it 'should not allow the upload' do
+            upload.original_filename = 'test.txt'
+            expect(subject.validate(upload)).to eq(nil)
+          end
+        end
+      end
+
+      describe 'for normal user' do
+        let(:user) { Fabricate(:user) }
+
+        it 'should not allow the upload' do
+          expect(subject.validate(upload)).to eq(nil)
+        end
+      end
+    end
   end
 end
diff --git a/spec/components/wizard/step_updater_spec.rb b/spec/components/wizard/step_updater_spec.rb
index 54b4535c487..b8687e9c396 100644
--- a/spec/components/wizard/step_updater_spec.rb
+++ b/spec/components/wizard/step_updater_spec.rb
@@ -214,38 +214,49 @@ describe Wizard::StepUpdater do
 
   context "logos step" do
     it "updates the fields correctly" do
-      updater = wizard.create_updater('logos',
-                                      logo_url: '/uploads/logo.png',
-                                      logo_small_url: '/uploads/logo-small.png')
+      upload = Fabricate(:upload)
+      upload2 = Fabricate(:upload)
+
+      updater = wizard.create_updater(
+        'logos',
+        logo: upload.url,
+        logo_small: upload2.url
+      )
+
       updater.update
 
       expect(updater).to be_success
       expect(wizard.completed_steps?('logos')).to eq(true)
-      expect(SiteSetting.logo_url).to eq('/uploads/logo.png')
-      expect(SiteSetting.logo_small_url).to eq('/uploads/logo-small.png')
+      expect(SiteSetting.logo).to eq(upload)
+      expect(SiteSetting.logo_small).to eq(upload2)
     end
   end
 
   context "icons step" do
     it "updates the fields correctly" do
+      upload = Fabricate(:upload)
+      upload2 = Fabricate(:upload)
+
       updater = wizard.create_updater('icons',
-                                      favicon_url: "/uploads/favicon.png",
-                                      apple_touch_icon_url: "/uploads/apple.png")
+        favicon: upload.url,
+        apple_touch_icon: upload2.url
+      )
+
       updater.update
 
       expect(updater).to be_success
       expect(wizard.completed_steps?('icons')).to eq(true)
-      expect(SiteSetting.favicon_url).to eq('/uploads/favicon.png')
-      expect(SiteSetting.apple_touch_icon_url).to eq('/uploads/apple.png')
+      expect(SiteSetting.favicon).to eq(upload)
+      expect(SiteSetting.apple_touch_icon).to eq(upload2)
     end
 
-    it "updates large_icon_url if the uploaded icon size is greater than 180x180" do
+    it "updates large_icon if the uploaded icon size is greater than 180x180" do
       upload = Fabricate(:upload, width: 512, height: 512)
-      updater = wizard.create_updater('icons', apple_touch_icon_url: upload.url)
+      updater = wizard.create_updater('icons', apple_touch_icon: upload.url)
       updater.update
 
       expect(updater).to be_success
-      expect(SiteSetting.large_icon_url).to eq(upload.url)
+      expect(SiteSetting.large_icon).to eq(upload)
     end
   end
 
diff --git a/spec/db/post_migrate/migrate_url_site_settings_spec.rb b/spec/db/post_migrate/migrate_url_site_settings_spec.rb
new file mode 100644
index 00000000000..8b931c67e0b
--- /dev/null
+++ b/spec/db/post_migrate/migrate_url_site_settings_spec.rb
@@ -0,0 +1,76 @@
+require 'rails_helper'
+require_relative '../../../db/post_migrate/20181112013117_migrate_url_site_settings'
+
+RSpec.describe MigrateUrlSiteSettings do
+  before do
+    SiteSetting.authorized_extensions = ''
+  end
+
+  it 'should migrate to the new upload site settings correctly' do
+    [
+      %w{logo_url /test.png},
+      %w{logo_small_url https://test.discourse.awesome/test.png},
+      %w{favicon_url http://test.discourse.awesome/some.ico},
+      %w{digest_logo_url /test.png},
+      %w{mobile_logo_url /test.png},
+      %w{large_icon_url /test.png},
+      %w{apple_touch_icon_url /test.png},
+      %w{default_opengraph_image_url /test.png},
+      %w{twitter_summary_large_image_url //omg.aws.somestack/test.png},
+      %w{push_notifications_icon_url //omg.aws.somestack/test.png}
+    ].each do |name, value|
+
+      SiteSetting.create!(
+        name: name,
+        value: value,
+        data_type: SiteSettings::TypeSupervisor.types[:string]
+      )
+    end
+
+    %w{
+      http://test.localhost/test.png
+      https://omg.aws.somestack/test.png
+    }.each do |url|
+      stub_request(:get, url).to_return(
+        status: 200, body: file_from_fixtures("smallest.png").read
+      )
+    end
+
+    stub_request(:get, "https://test.discourse.awesome/test.png")
+      .to_return(status: 200, body: file_from_fixtures("downsized.png").read)
+
+    stub_request(:get, "http://test.discourse.awesome/some.ico")
+      .to_return(status: 200, body: file_from_fixtures("smallest.ico").read)
+
+    begin
+      STDOUT.stubs(:write)
+      expect { MigrateUrlSiteSettings.new.up }.to change { Upload.count }.by(3)
+    ensure
+      STDOUT.unstub(:write)
+    end
+
+    upload = Upload.find_by(original_filename: "logo.png")
+    upload2 = Upload.find_by(original_filename: "logo_small.png")
+    upload3 = Upload.find_by(original_filename: "favicon.ico")
+
+    expect(SiteSetting.logo_small).to eq(upload2)
+    expect(SiteSetting.logo_small.is_a?(Upload)).to eq(true)
+
+    expect(SiteSetting.favicon).to eq(upload3)
+    expect(SiteSetting.favicon.is_a?(Upload)).to eq(true)
+
+    %i{
+      logo
+      digest_logo
+      mobile_logo
+      large_icon
+      apple_touch_icon
+      opengraph_image
+      twitter_summary_large_image
+      push_notifications_icon
+    }.each do |setting|
+      expect(SiteSetting.public_send(setting)).to eq(upload)
+      expect(SiteSetting.public_send(setting).is_a?(Upload)).to eq(true)
+    end
+  end
+end
diff --git a/spec/fixtures/images/smallest.ico b/spec/fixtures/images/smallest.ico
new file mode 100644
index 00000000000..d4edd507993
Binary files /dev/null and b/spec/fixtures/images/smallest.ico differ
diff --git a/spec/jobs/clean_up_uploads_spec.rb b/spec/jobs/clean_up_uploads_spec.rb
index e73d199d352..b8957b683ba 100644
--- a/spec/jobs/clean_up_uploads_spec.rb
+++ b/spec/jobs/clean_up_uploads_spec.rb
@@ -44,7 +44,54 @@ describe Jobs::CleanUpUploads do
     end
   end
 
-  it "does not clean up uploads in site settings" do
+  it 'does not clean up upload site settings' do
+    begin
+      original_provider = SiteSetting.provider
+      SiteSetting.provider = SiteSettings::DbProvider.new(SiteSetting)
+
+      logo_upload = fabricate_upload
+      logo_small_upload = fabricate_upload
+      digest_logo_upload = fabricate_upload
+      mobile_logo_upload = fabricate_upload
+      large_icon_upload = fabricate_upload
+      opengraph_image_upload = fabricate_upload
+      twitter_summary_large_image_upload = fabricate_upload
+      favicon_upload = fabricate_upload
+      apple_touch_icon_upload = fabricate_upload
+
+      SiteSetting.logo = logo_upload
+      SiteSetting.logo_small = logo_small_upload
+      SiteSetting.digest_logo = digest_logo_upload
+      SiteSetting.mobile_logo = mobile_logo_upload
+      SiteSetting.large_icon = large_icon_upload
+      SiteSetting.opengraph_image = opengraph_image_upload
+
+      SiteSetting.twitter_summary_large_image =
+        twitter_summary_large_image_upload
+
+      SiteSetting.favicon = favicon_upload
+      SiteSetting.apple_touch_icon = apple_touch_icon_upload
+
+      Jobs::CleanUpUploads.new.execute(nil)
+
+      [
+        logo_upload,
+        logo_small_upload,
+        digest_logo_upload,
+        mobile_logo_upload,
+        large_icon_upload,
+        opengraph_image_upload,
+        twitter_summary_large_image_upload,
+        favicon_upload,
+        apple_touch_icon_upload
+      ].each { |record| expect(Upload.exists?(id: record.id)).to eq(true) }
+    ensure
+      SiteSetting.delete_all
+      SiteSetting.provider = original_provider
+    end
+  end
+
+  it "does not clean up uploads with URLs used in site settings" do
     logo_upload = fabricate_upload
     logo_small_upload = fabricate_upload
     digest_logo_upload = fabricate_upload
diff --git a/spec/lib/upload_creator_spec.rb b/spec/lib/upload_creator_spec.rb
index 5b0831355d6..43cd261766c 100644
--- a/spec/lib/upload_creator_spec.rb
+++ b/spec/lib/upload_creator_spec.rb
@@ -37,6 +37,26 @@ RSpec.describe UploadCreator do
       end
     end
 
+    describe 'when image is not authorized' do
+      describe 'when image is for site setting' do
+        let(:filename) { 'logo.png' }
+        let(:file) { file_from_fixtures(filename) }
+
+        before do
+          SiteSetting.authorized_extensions = 'jpg'
+        end
+
+        it 'should create the right upload' do
+          upload = UploadCreator.new(file, filename,
+            for_site_setting: true
+          ).create_for(Discourse.system_user.id)
+
+          expect(upload.persisted?).to eq(true)
+          expect(upload.original_filename).to eq(filename)
+        end
+      end
+    end
+
     describe 'when image has the wrong extension' do
       let(:filename) { "png_as.bin" }
       let(:file) { file_from_fixtures(filename) }
diff --git a/spec/models/upload_spec.rb b/spec/models/upload_spec.rb
index 70b7760a385..f3b88c01984 100644
--- a/spec/models/upload_spec.rb
+++ b/spec/models/upload_spec.rb
@@ -222,4 +222,10 @@ describe Upload do
     end
   end
 
+  describe '#to_s' do
+    it 'should return the right value' do
+      expect(upload.to_s).to eq(upload.url)
+    end
+  end
+
 end
diff --git a/spec/requests/admin/site_settings_controller_spec.rb b/spec/requests/admin/site_settings_controller_spec.rb
index fd17c3dc392..98c4586c3b9 100644
--- a/spec/requests/admin/site_settings_controller_spec.rb
+++ b/spec/requests/admin/site_settings_controller_spec.rb
@@ -31,6 +31,7 @@ describe Admin::SiteSettingsController do
     describe '#update' do
       before do
         SiteSetting.setting(:test_setting, "default")
+        SiteSetting.setting(:test_upload, "", type: :upload)
         SiteSetting.refresh!
       end
 
@@ -50,6 +51,33 @@ describe Admin::SiteSettingsController do
         expect(SiteSetting.test_setting).to eq('')
       end
 
+      it 'allows upload site settings to be updated' do
+        upload = Fabricate(:upload)
+
+        put "/admin/site_settings/test_upload.json", params: {
+          test_upload: upload.url
+        }
+
+        expect(response.status).to eq(200)
+        expect(SiteSetting.test_upload).to eq(upload)
+
+        user_history = UserHistory.last
+
+        expect(user_history.action).to eq(
+          UserHistory.actions[:change_site_setting]
+        )
+
+        expect(user_history.previous_value).to eq(nil)
+        expect(user_history.new_value).to eq(upload.url)
+
+        put "/admin/site_settings/test_upload.json", params: {
+          test_upload: nil
+        }
+
+        expect(response.status).to eq(200)
+        expect(SiteSetting.test_upload).to eq(nil)
+      end
+
       it 'logs the change' do
         SiteSetting.test_setting = 'previous'
 
diff --git a/spec/requests/metadata_controller_spec.rb b/spec/requests/metadata_controller_spec.rb
index 323d06cfe4c..2047b13277f 100644
--- a/spec/requests/metadata_controller_spec.rb
+++ b/spec/requests/metadata_controller_spec.rb
@@ -1,11 +1,13 @@
 require 'rails_helper'
 
 RSpec.describe MetadataController do
+  let(:upload) { Fabricate(:upload) }
+
   describe 'manifest.webmanifest' do
     it 'returns the right output' do
       title = 'MyApp'
       SiteSetting.title = title
-      SiteSetting.large_icon_url = "http://big.square/png"
+      SiteSetting.large_icon = upload
 
       get "/manifest.webmanifest"
       expect(response.status).to eq(200)
@@ -13,19 +15,28 @@ RSpec.describe MetadataController do
       manifest = JSON.parse(response.body)
 
       expect(manifest["name"]).to eq(title)
-      expect(manifest["icons"].first["src"]).to eq("http://big.square/png")
+
+      expect(manifest["icons"].first["src"]).to eq(
+        UrlHelper.absolute(upload.url)
+      )
     end
 
     it 'can guess mime types' do
-      SiteSetting.large_icon_url = "http://big.square/ico.jpg"
+      upload = Fabricate(:upload,
+        original_filename: 'test.jpg',
+        extension: 'jpg'
+      )
+
+      SiteSetting.large_icon = upload
       get "/manifest.webmanifest"
+
       expect(response.status).to eq(200)
       manifest = JSON.parse(response.body)
       expect(manifest["icons"].first["type"]).to eq("image/jpeg")
     end
 
     it 'defaults to png' do
-      SiteSetting.large_icon_url = "http://big.square/noidea.bogus"
+      SiteSetting.large_icon = upload
       get "/manifest.webmanifest"
       expect(response.status).to eq(200)
       manifest = JSON.parse(response.body)
@@ -57,15 +68,15 @@ RSpec.describe MetadataController do
   describe 'opensearch.xml' do
     it 'returns the right output' do
       title = 'MyApp'
-      favicon_path = '/uploads/something/23432.png'
       SiteSetting.title = title
-      SiteSetting.favicon_url = favicon_path
+      SiteSetting.favicon = upload
       get "/opensearch.xml"
+
       expect(response.status).to eq(200)
       expect(response.body).to include(title)
       expect(response.body).to include("/search?q={searchTerms}")
       expect(response.body).to include('image/png')
-      expect(response.body).to include(favicon_path)
+      expect(response.body).to include(UrlHelper.absolute(upload.url))
       expect(response.content_type).to eq('application/xml')
     end
   end
diff --git a/spec/requests/site_controller_spec.rb b/spec/requests/site_controller_spec.rb
index 9cbf0461fa6..5483ea72f56 100644
--- a/spec/requests/site_controller_spec.rb
+++ b/spec/requests/site_controller_spec.rb
@@ -1,33 +1,36 @@
 require 'rails_helper'
 
 describe SiteController do
-  describe '.basic_info' do
+  describe '#basic_info' do
     it 'is visible always even for sites requiring login' do
-      SiteSetting.login_required = true
+      upload = Fabricate(:upload)
 
+      SiteSetting.login_required = true
       SiteSetting.title = "Hammer Time"
       SiteSetting.site_description = "A time for Hammer"
-      SiteSetting.logo_url = "/uploads/logo.png"
-      SiteSetting.logo_small_url = "http://boom.com/uploads/logo_small.png"
-      SiteSetting.apple_touch_icon_url = "https://boom.com/apple/logo.png"
-      SiteSetting.mobile_logo_url = "https://a.a/a.png"
+      SiteSetting.logo = upload
+      SiteSetting.logo_small = upload
+      SiteSetting.apple_touch_icon = upload
+      SiteSetting.mobile_logo = upload
       Theme.clear_default!
 
       get "/site/basic-info.json"
       json = JSON.parse(response.body)
 
+      expected_url = UrlHelper.absolute(upload.url)
+
       expect(json["title"]).to eq("Hammer Time")
       expect(json["description"]).to eq("A time for Hammer")
-      expect(json["logo_url"]).to eq("http://test.localhost/uploads/logo.png")
-      expect(json["apple_touch_icon_url"]).to eq("https://boom.com/apple/logo.png")
-      expect(json["logo_small_url"]).to eq("http://boom.com/uploads/logo_small.png")
-      expect(json["mobile_logo_url"]).to eq("https://a.a/a.png")
+      expect(json["logo_url"]).to eq(expected_url)
+      expect(json["apple_touch_icon_url"]).to eq(expected_url)
+      expect(json["logo_small_url"]).to eq(expected_url)
+      expect(json["mobile_logo_url"]).to eq(expected_url)
       expect(json["header_primary_color"]).to eq("333333")
       expect(json["header_background_color"]).to eq("ffffff")
     end
   end
 
-  describe '.statistics' do
+  describe '#statistics' do
     it 'is visible for sites requiring login' do
       SiteSetting.login_required = true
       SiteSetting.share_anonymized_statistics = true
diff --git a/spec/requests/static_controller_spec.rb b/spec/requests/static_controller_spec.rb
index 8da03358d93..df12d0d6d2b 100644
--- a/spec/requests/static_controller_spec.rb
+++ b/spec/requests/static_controller_spec.rb
@@ -1,19 +1,22 @@
 require 'rails_helper'
 
 describe StaticController do
+  let(:upload) { Fabricate(:upload) }
 
   context '#favicon' do
     let(:png) { Base64.decode64("R0lGODlhAQABALMAAAAAAIAAAACAAICAAAAAgIAAgACAgMDAwICAgP8AAAD/AP//AAAA//8A/wD//wBiZCH5BAEAAA8ALAAAAAABAAEAAAQC8EUAOw==") }
 
     before { FinalDestination.stubs(:lookup_ip).returns("1.2.3.4") }
 
+    after do
+      $redis.flushall
+    end
+
     it 'returns the default favicon for a missing download' do
-      url = "https://fav.icon/#{SecureRandom.hex}.png"
-
+      url = UrlHelper.absolute(upload.url)
+      SiteSetting.favicon = upload
       stub_request(:get, url).to_return(status: 404)
 
-      SiteSetting.favicon_url = url
-
       get '/favicon/proxied'
 
       favicon = File.read(Rails.root + "public/images/default-favicon.png")
@@ -24,12 +27,10 @@ describe StaticController do
     end
 
     it 'can proxy a favicon correctly' do
-      url = "https://fav.icon/#{SecureRandom.hex}.png"
-
+      url = UrlHelper.absolute(upload.url)
+      SiteSetting.favicon = upload
       stub_request(:get, url).to_return(status: 200, body: png)
 
-      SiteSetting.favicon_url = url
-
       get '/favicon/proxied'
 
       expect(response.status).to eq(200)
diff --git a/spec/requests/uploads_controller_spec.rb b/spec/requests/uploads_controller_spec.rb
index 542365cd60f..f6e76930e3e 100644
--- a/spec/requests/uploads_controller_spec.rb
+++ b/spec/requests/uploads_controller_spec.rb
@@ -124,7 +124,26 @@ describe UploadsController do
 
         expect(response.status).to eq(200)
         id = JSON.parse(response.body)["id"]
-        expect(id).to be_present
+        expect(Upload.last.id).to eq(id)
+      end
+
+      it 'allows staff to upload supported images for site settings' do
+        SiteSetting.authorized_extensions = ''
+        user.update!(admin: true)
+
+        post "/uploads.json", params: {
+          file: logo,
+          type: "site_setting",
+          for_site_setting: "true",
+        }
+
+        expect(response.status).to eq(200)
+        id = JSON.parse(response.body)["id"]
+
+        upload = Upload.last
+
+        expect(upload.id).to eq(id)
+        expect(upload.original_filename).to eq('logo.png')
       end
 
       it 'respects `authorized_extensions_for_staff` setting when staff upload file' do
diff --git a/test/javascripts/acceptance/admin-site-settings-test.js.es6 b/test/javascripts/acceptance/admin-site-settings-test.js.es6
index 18c79d2869b..a4bb84f0c03 100644
--- a/test/javascripts/acceptance/admin-site-settings-test.js.es6
+++ b/test/javascripts/acceptance/admin-site-settings-test.js.es6
@@ -10,6 +10,17 @@ acceptance("Admin - Site Settings", {
   }
 });
 
+QUnit.test("upload site setting", async assert => {
+  await visit("/admin/site_settings");
+
+  assert.ok(
+    exists(".row.setting.upload .image-uploader"),
+    "image uploader is present"
+  );
+
+  assert.ok(exists(".row.setting.upload .undo"), "undo button is present");
+});
+
 QUnit.test("changing value updates dirty state", async assert => {
   await visit("/admin/site_settings");
   await fillIn("#setting-filter", "title");
diff --git a/test/javascripts/fixtures/site_settings.js.es6 b/test/javascripts/fixtures/site_settings.js.es6
index 7d7afed3ea9..cf48b6c10be 100644
--- a/test/javascripts/fixtures/site_settings.js.es6
+++ b/test/javascripts/fixtures/site_settings.js.es6
@@ -33,6 +33,16 @@ export default {
         secret: false,
         type: "username"
       },
+      {
+        setting: "logo",
+        description: "Some logo",
+        default: "",
+        value: "/some/image",
+        category: "required",
+        preview: null,
+        secret: false,
+        type: "upload"
+      },
       {
         setting: "top_menu",
         description:
diff --git a/test/javascripts/helpers/site-settings.js b/test/javascripts/helpers/site-settings.js
index fd4a29b8b34..3065d01a68c 100644
--- a/test/javascripts/helpers/site-settings.js
+++ b/test/javascripts/helpers/site-settings.js
@@ -1,95 +1,103 @@
 /*jshint maxlen:10000000 */
 Discourse.SiteSettingsOriginal = {
-  "title":"Discourse Meta",
-  "logo_url":"/assets/logo.png",
-  "logo_small_url":"/assets/logo-single.png",
-  "mobile_logo_url":"",
-  "favicon_url":"//meta.discourse.org/uploads/default/2499/79d53726406d87af.ico",
-  "allow_user_locale":false,
-  "suggested_topics":7,
-  "ga_universal_tracking_code":"",
-  "ga_universal_domain_name":"auto",
-  "top_menu":"latest|new|unread|categories|top",
-  "post_menu":"like-count|like|share|flag|edit|bookmark|delete|admin|reply",
-  "post_menu_hidden_items":"flag|edit|delete|admin",
-  "share_links":"twitter|facebook|google+|email",
-  "category_colors":"BF1E2E|F1592A|F7941D|9EB83B|3AB54A|12A89D|25AAE2|0E76BD|652D90|92278F|ED207B|8C6238|231F20|27AA5B|B3B5B4|E45735",
-  "enable_mobile_theme":true,
-  "relative_date_duration":14,
-  "fixed_category_positions":false,
-  "enable_badges":true,
-  "invite_only":false,
-  "login_required":false,
-  "must_approve_users":false,
-  "enable_local_logins":true,
-  "allow_new_registrations":true,
-  "enable_google_logins":true,
-  "enable_google_oauth2_logins":false,
-  "enable_yahoo_logins":true,
-  "enable_twitter_logins":true,
-  "enable_facebook_logins":true,
-  "enable_github_logins":true,
-  "enable_sso":false,
-  "min_username_length":3,
-  "max_username_length":20,
-  "min_password_length":8,
-  "enable_names":true,
-  "invites_shown":30,
-  "delete_user_max_post_age":60,
-  "delete_all_posts_max":15,
-  "min_post_length":20,
-  "min_personal_message_post_length":10,
-  "max_post_length":32000,
-  "min_topic_title_length":15,
-  "max_topic_title_length":255,
-  "min_personal_message_title_length":2,
-  "allow_uncategorized_topics":true,
-  "min_title_similar_length":10,
-  "edit_history_visible_to_public":true,
-  "delete_removed_posts_after":24,
-  "traditional_markdown_linebreaks":false,
-  "suppress_reply_directly_below":true,
-  "suppress_reply_directly_above":true,
-  "newuser_max_images":0,
-  "newuser_max_attachments":0,
-  "display_name_on_posts":true,
-  "short_progress_text_threshold":10000,
-  "default_code_lang":"auto",
-  "autohighlight_all_code":false,
-  "email_in":false,
-  "authorized_extensions":".jpg|.jpeg|.png|.gif|.svg|.txt|.ico|.yml",
-  "authorized_extensions_for_staff": "",
-  "max_image_width":690,
-  "max_image_height":500,
-  "allow_profile_backgrounds":true,
-  "allow_uploaded_avatars":true,
-  "allow_animated_avatars":false,
-  "tl1_requires_read_posts":30,
-  "enable_long_polling":true,
-  "polling_interval":3000,
-  "anon_polling_interval":30000,
-  "flush_timings_secs":5,
-  "enable_user_directory":true,
-  "tos_url":"",
-  "privacy_policy_url":"",
-  "tos_accept_required":false,
-  "faq_url":"",
-  "allow_restore":false,
-  "maximum_backups":5,
-  "version_checks":true,
-  "suppress_uncategorized_badge":true,
-  "min_search_term_length":3,
-  "topic_views_heat_low":1000,
-  "topic_views_heat_medium":2000,
-  "topic_views_heat_high":5000,
-  "global_notice":"",
-  "show_create_topics_notice":true,
-  "available_locales":"cs|da|de|en|es|fr|he|id|it|ja|ko|nb_NO|nl|pl_PL|pt|pt_BR|ru|sv|uk|zh_CN|zh_TW",
-  "highlighted_languages":"apache|bash|cs|cpp|css|coffeescript|diff|xml|http|ini|json|java|javascript|makefile|markdown|nginx|objectivec|ruby|perl|php|python|sql|handlebars",
-  "enable_emoji":true,
-  "emoji_set":"emoji_one",
-  "desktop_category_page_style":"categories_and_latest_topics",
-  "enable_mentions":true,
-  "enable_personal_messages": true
+  title: "Discourse Meta",
+  site_logo_url: "/assets/logo.png",
+  site_logo_small_url: "/assets/logo-single.png",
+  site_mobile_logo_url: "",
+  site_favicon_url:
+    "//meta.discourse.org/uploads/default/2499/79d53726406d87af.ico",
+  allow_user_locale: false,
+  suggested_topics: 7,
+  ga_universal_tracking_code: "",
+  ga_universal_domain_name: "auto",
+  top_menu: "latest|new|unread|categories|top",
+  post_menu: "like-count|like|share|flag|edit|bookmark|delete|admin|reply",
+  post_menu_hidden_items: "flag|edit|delete|admin",
+  share_links: "twitter|facebook|google+|email",
+  category_colors:
+    "BF1E2E|F1592A|F7941D|9EB83B|3AB54A|12A89D|25AAE2|0E76BD|652D90|92278F|ED207B|8C6238|231F20|27AA5B|B3B5B4|E45735",
+  enable_mobile_theme: true,
+  relative_date_duration: 14,
+  fixed_category_positions: false,
+  enable_badges: true,
+  invite_only: false,
+  login_required: false,
+  must_approve_users: false,
+  enable_local_logins: true,
+  allow_new_registrations: true,
+  enable_google_logins: true,
+  enable_google_oauth2_logins: false,
+  enable_yahoo_logins: true,
+  enable_twitter_logins: true,
+  enable_facebook_logins: true,
+  enable_github_logins: true,
+  enable_sso: false,
+  min_username_length: 3,
+  max_username_length: 20,
+  min_password_length: 8,
+  enable_names: true,
+  invites_shown: 30,
+  delete_user_max_post_age: 60,
+  delete_all_posts_max: 15,
+  min_post_length: 20,
+  min_personal_message_post_length: 10,
+  max_post_length: 32000,
+  min_topic_title_length: 15,
+  max_topic_title_length: 255,
+  min_personal_message_title_length: 2,
+  allow_uncategorized_topics: true,
+  min_title_similar_length: 10,
+  edit_history_visible_to_public: true,
+  delete_removed_posts_after: 24,
+  traditional_markdown_linebreaks: false,
+  suppress_reply_directly_below: true,
+  suppress_reply_directly_above: true,
+  newuser_max_images: 0,
+  newuser_max_attachments: 0,
+  display_name_on_posts: true,
+  short_progress_text_threshold: 10000,
+  default_code_lang: "auto",
+  autohighlight_all_code: false,
+  email_in: false,
+  authorized_extensions: ".jpg|.jpeg|.png|.gif|.svg|.txt|.ico|.yml",
+  authorized_extensions_for_staff: "",
+  max_image_width: 690,
+  max_image_height: 500,
+  allow_profile_backgrounds: true,
+  allow_uploaded_avatars: true,
+  allow_animated_avatars: false,
+  tl1_requires_read_posts: 30,
+  enable_long_polling: true,
+  polling_interval: 3000,
+  anon_polling_interval: 30000,
+  flush_timings_secs: 5,
+  enable_user_directory: true,
+  tos_url: "",
+  privacy_policy_url: "",
+  tos_accept_required: false,
+  faq_url: "",
+  allow_restore: false,
+  maximum_backups: 5,
+  version_checks: true,
+  suppress_uncategorized_badge: true,
+  min_search_term_length: 3,
+  topic_views_heat_low: 1000,
+  topic_views_heat_medium: 2000,
+  topic_views_heat_high: 5000,
+  global_notice: "",
+  show_create_topics_notice: true,
+  available_locales:
+    "cs|da|de|en|es|fr|he|id|it|ja|ko|nb_NO|nl|pl_PL|pt|pt_BR|ru|sv|uk|zh_CN|zh_TW",
+  highlighted_languages:
+    "apache|bash|cs|cpp|css|coffeescript|diff|xml|http|ini|json|java|javascript|makefile|markdown|nginx|objectivec|ruby|perl|php|python|sql|handlebars",
+  enable_emoji: true,
+  emoji_set: "emoji_one",
+  desktop_category_page_style: "categories_and_latest_topics",
+  enable_mentions: true,
+  enable_personal_messages: true
 };
-Discourse.SiteSettings = jQuery.extend(true, {}, Discourse.SiteSettingsOriginal);
+Discourse.SiteSettings = jQuery.extend(
+  true,
+  {},
+  Discourse.SiteSettingsOriginal
+);
diff --git a/test/javascripts/widgets/home-logo-test.js.es6 b/test/javascripts/widgets/home-logo-test.js.es6
index 9911a3345ce..4a6fb874d3c 100644
--- a/test/javascripts/widgets/home-logo-test.js.es6
+++ b/test/javascripts/widgets/home-logo-test.js.es6
@@ -10,8 +10,8 @@ const title = "Cool Forum";
 widgetTest("basics", {
   template: '{{mount-widget widget="home-logo" args=args}}',
   beforeEach() {
-    this.siteSettings.logo_url = bigLogo;
-    this.siteSettings.logo_small_url = smallLogo;
+    this.siteSettings.site_logo_url = bigLogo;
+    this.siteSettings.site_logo_small_url = smallLogo;
     this.siteSettings.title = title;
     this.set("args", { minimized: false });
   },
@@ -28,8 +28,8 @@ widgetTest("basics", {
 widgetTest("basics - minimized", {
   template: '{{mount-widget widget="home-logo" args=args}}',
   beforeEach() {
-    this.siteSettings.logo_url = bigLogo;
-    this.siteSettings.logo_small_url = smallLogo;
+    this.siteSettings.site_logo_url = bigLogo;
+    this.siteSettings.site_logo_small_url = smallLogo;
     this.siteSettings.title = title;
     this.set("args", { minimized: true });
   },
@@ -44,8 +44,8 @@ widgetTest("basics - minimized", {
 widgetTest("no logo", {
   template: '{{mount-widget widget="home-logo" args=args}}',
   beforeEach() {
-    this.siteSettings.logo_url = "";
-    this.siteSettings.logo_small_url = "";
+    this.siteSettings.site_logo_url = "";
+    this.siteSettings.site_logo_small_url = "";
     this.siteSettings.title = title;
     this.set("args", { minimized: false });
   },
@@ -59,8 +59,8 @@ widgetTest("no logo", {
 widgetTest("no logo - minimized", {
   template: '{{mount-widget widget="home-logo" args=args}}',
   beforeEach() {
-    this.siteSettings.logo_url = "";
-    this.siteSettings.logo_small_url = "";
+    this.siteSettings.site_logo_url = "";
+    this.siteSettings.site_logo_small_url = "";
     this.siteSettings.title = title;
     this.set("args", { minimized: true });
   },
@@ -73,8 +73,8 @@ widgetTest("no logo - minimized", {
 widgetTest("mobile logo", {
   template: '{{mount-widget widget="home-logo" args=args}}',
   beforeEach() {
-    this.siteSettings.mobile_logo_url = mobileLogo;
-    this.siteSettings.logo_small_url = smallLogo;
+    this.siteSettings.site_mobile_logo_url = mobileLogo;
+    this.siteSettings.site_logo_small_url = smallLogo;
     this.site.mobileView = true;
   },
 
@@ -87,7 +87,7 @@ widgetTest("mobile logo", {
 widgetTest("mobile without logo", {
   template: '{{mount-widget widget="home-logo" args=args}}',
   beforeEach() {
-    this.siteSettings.logo_url = bigLogo;
+    this.siteSettings.site_logo_url = bigLogo;
     this.site.mobileView = true;
   },
 
@@ -101,8 +101,8 @@ widgetTest("basics, subfolder", {
   template: '{{mount-widget widget="home-logo" args=args}}',
   beforeEach() {
     Discourse.BaseUri = "/forum";
-    this.siteSettings.logo_url = bigLogo;
-    this.siteSettings.logo_small_url = smallLogo;
+    this.siteSettings.site_logo_url = bigLogo;
+    this.siteSettings.site_logo_small_url = smallLogo;
     this.siteSettings.title = title;
     this.set("args", { minimized: false });
   },
@@ -118,8 +118,8 @@ widgetTest("basics, subfolder - minimized", {
   template: '{{mount-widget widget="home-logo" args=args}}',
   beforeEach() {
     Discourse.BaseUri = "/forum";
-    this.siteSettings.logo_url = bigLogo;
-    this.siteSettings.logo_small_url = smallLogo;
+    this.siteSettings.site_logo_url = bigLogo;
+    this.siteSettings.site_logo_small_url = smallLogo;
     this.siteSettings.title = title;
     this.set("args", { minimized: true });
   },
@@ -135,8 +135,8 @@ widgetTest("mobile logo, subfolder", {
   template: '{{mount-widget widget="home-logo" args=args}}',
   beforeEach() {
     Discourse.BaseUri = "/forum";
-    this.siteSettings.mobile_logo_url = mobileLogo;
-    this.siteSettings.logo_small_url = smallLogo;
+    this.siteSettings.site_mobile_logo_url = mobileLogo;
+    this.siteSettings.site_logo_small_url = smallLogo;
     this.site.mobileView = true;
   },