diff --git a/Gemfile b/Gemfile
index 8b29154be..95ddcbb4d 100644
--- a/Gemfile
+++ b/Gemfile
@@ -47,6 +47,7 @@ gem 'redcarpet', '~> 3.5'
 gem 'simple_form'
 gem 'tinymce-rails'
 gem 'image_processing', '~> 1.2'
+gem 'puppeteer-ruby'
 gem 'react-rails'
 gem 'webpacker'
 
diff --git a/Gemfile.lock b/Gemfile.lock
index 93db6869f..95bdc765a 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -345,6 +345,10 @@ GEM
       nio4r (~> 2.0)
     pundit (2.1.1)
       activesupport (>= 3.0.0)
+    puppeteer-ruby (0.40.7)
+      concurrent-ruby (~> 1.1.0)
+      mime-types (>= 3.0)
+      websocket-driver (>= 0.6.0)
     racc (1.6.0)
     rack (2.2.3.1)
     rack-mini-profiler (2.3.3)
@@ -556,6 +560,7 @@ DEPENDENCIES
   pry-rescue
   puma
   pundit
+  puppeteer-ruby
   rack-mini-profiler
   rack-timeout (~> 0.5)
   rails (~> 6.1.4)
diff --git a/app/controllers/staff/pages_controller.rb b/app/controllers/staff/pages_controller.rb
index 8a463009d..809e69b2d 100644
--- a/app/controllers/staff/pages_controller.rb
+++ b/app/controllers/staff/pages_controller.rb
@@ -11,6 +11,7 @@ def index
 
   def show
     @body = params[:preview] || @page.unpublished_body || ""
+    @include_tailwind = true
     render template: 'pages/show', layout: "themes/#{current_website.theme}"
   end
 
@@ -39,6 +40,8 @@ def update
   def preview; end
 
   def publish
+    save_tailwind_page_content
+
     @page.update(published_body: @page.unpublished_body,
                  body_published_at: Time.current)
     flash[:success] = "#{@page.name} Page was successfully published."
@@ -67,6 +70,24 @@ def set_page
             end
   end
 
+  def save_tailwind_page_content
+    Puppeteer.launch(args: ['--no-sandbox', '--disable-setuid-sandbox']) do |browser|
+      page = browser.pages.first || browser.new_page
+      page.goto(root_url)
+      cookies.each do |name, value|
+        page.set_cookie(name: name, value: value)
+      end
+      page.goto(event_staff_page_url(current_event, @page), wait_until: 'domcontentloaded')
+      css = page.query_selector_all('style').map do |style|
+        style.evaluate('(el) => el.textContent')
+      end.detect { |text| text.match("tailwindcss") }
+      html = "<style>#{css}</style>"
+
+      content = @page.contents.find_or_initialize_by(name: Page::TAILWIND)
+      content.update!(placement: Website::Content::HEAD, html: html)
+    end
+  end
+
   def build_page
     if template = params[:page] && page_params[:template].presence
       Page.from_template(
diff --git a/app/helpers/page_helper.rb b/app/helpers/page_helper.rb
index bdbf126c3..c6443275b 100644
--- a/app/helpers/page_helper.rb
+++ b/app/helpers/page_helper.rb
@@ -36,4 +36,10 @@ def background_style
   def logo_image(args)
     resize_image_tag(current_website.logo, **args)
   end
+
+  def tailwind_content
+    return false if @include_tailwind
+
+    @page&.tailwind_css&.html_safe
+  end
 end
diff --git a/app/javascript/packs/default_theme.js b/app/javascript/packs/default_theme.js
new file mode 100644
index 000000000..72ef077f8
--- /dev/null
+++ b/app/javascript/packs/default_theme.js
@@ -0,0 +1 @@
+import "controllers"
diff --git a/app/models/page.rb b/app/models/page.rb
index e77807361..f5edd5adc 100644
--- a/app/models/page.rb
+++ b/app/models/page.rb
@@ -4,9 +4,13 @@ class Page < ApplicationRecord
     'home' => { },
   }
 
+  TAILWIND = 'tailwind'.freeze
+
   belongs_to :website
   after_save_commit :purge_website_cache
 
+  has_many :contents, class_name: 'Website::Content', as: :contentable, dependent: :destroy
+
   scope :published, -> { where.not(published_body: nil).where(hide_page: false) }
   scope :in_footer, -> { published.where.not(footer_category: [nil, ""]) }
 
@@ -39,6 +43,10 @@ def unpublished_changes?
     published_body != unpublished_body
   end
 
+  def tailwind_css
+    contents.where(name: TAILWIND).pluck(:html).first
+  end
+
   private
 
   def purge_website_cache
diff --git a/app/models/website.rb b/app/models/website.rb
index e355fc7dd..a5ca3eaa4 100644
--- a/app/models/website.rb
+++ b/app/models/website.rb
@@ -4,7 +4,7 @@ class Website < ApplicationRecord
   belongs_to :event
   has_many :pages, dependent: :destroy
   has_many :fonts, class_name: 'Website::Font', dependent: :destroy
-  has_many :contents, class_name: 'Website::Content', dependent: :destroy
+  has_many :contents, class_name: 'Website::Content', as: :contentable, dependent: :destroy
   has_one :meta_data, class_name: 'Website::MetaData', dependent: :destroy
 
   has_many :session_formats, through: :event
diff --git a/app/models/website/content.rb b/app/models/website/content.rb
index fe61a5df4..ab7551ba6 100644
--- a/app/models/website/content.rb
+++ b/app/models/website/content.rb
@@ -4,9 +4,10 @@ class Website::Content < ApplicationRecord
     FOOTER = "footer",
   ].freeze
 
-  belongs_to :website
+  belongs_to :contentable, polymorphic: true
 
   scope :for, -> (placement) { where(placement: placement) }
+  scope :for_page, -> (slug) { where(name: slug) }
 end
 
 # == Schema Information
diff --git a/app/views/layouts/themes/default.html.haml b/app/views/layouts/themes/default.html.haml
index 95a18ac72..cc7716dfa 100644
--- a/app/views/layouts/themes/default.html.haml
+++ b/app/views/layouts/themes/default.html.haml
@@ -21,11 +21,11 @@
     %meta{property: "twitter:image", content: current_website.meta_image_url}
 
     = stylesheet_link_tag current_website.theme, media: 'all'
-    = javascript_pack_tag "application"
+    = javascript_pack_tag "default_theme"
     :css
       #{current_website.font_faces_css}
       #{current_website.font_root_css}
-    = javascript_pack_tag "tailwind"
+    = tailwind_content || javascript_pack_tag("tailwind")
     = current_website.head_content
 
   %body
@@ -58,4 +58,4 @@
         })
     = current_website.footer_content
 
-    = yield :javascript
\ No newline at end of file
+    = yield :javascript
diff --git a/db/migrate/20220609140626_convert_website_contents_to_polymorphic.rb b/db/migrate/20220609140626_convert_website_contents_to_polymorphic.rb
new file mode 100644
index 000000000..e402ebbf2
--- /dev/null
+++ b/db/migrate/20220609140626_convert_website_contents_to_polymorphic.rb
@@ -0,0 +1,10 @@
+class ConvertWebsiteContentsToPolymorphic < ActiveRecord::Migration[6.1]
+  def change
+    change_table :website_contents, bulk: true do |t|
+      t.rename :website_id, :contentable_id
+      t.string :contentable_type, default: 'Website', null: false
+      t.index [:contentable_id, :contentable_type]
+      t.remove_index :contentable_id
+    end
+  end
+end
diff --git a/db/schema.rb b/db/schema.rb
index 910c0c409..c26da9691 100644
--- a/db/schema.rb
+++ b/db/schema.rb
@@ -10,7 +10,7 @@
 #
 # It's strongly recommended that you check this file into your version control system.
 
-ActiveRecord::Schema.define(version: 2022_05_23_185412) do
+ActiveRecord::Schema.define(version: 2022_06_09_140626) do
 
   # These are extensions that must be enabled in order to support this database
   enable_extension "plpgsql"
@@ -344,10 +344,11 @@
     t.text "html"
     t.string "placement", default: "head", null: false
     t.string "name"
-    t.bigint "website_id"
+    t.bigint "contentable_id"
     t.datetime "created_at", precision: 6, null: false
     t.datetime "updated_at", precision: 6, null: false
-    t.index ["website_id"], name: "index_website_contents_on_website_id"
+    t.string "contentable_type", default: "Website", null: false
+    t.index ["contentable_id", "contentable_type"], name: "index_website_contents_on_contentable_id_and_contentable_type"
   end
 
   create_table "website_fonts", force: :cascade do |t|
diff --git a/spec/features/website/configuration_spec.rb b/spec/features/website/configuration_spec.rb
index 0b9f10d97..608b2a2e6 100644
--- a/spec/features/website/configuration_spec.rb
+++ b/spec/features/website/configuration_spec.rb
@@ -71,7 +71,7 @@
     website = create(:website, event: event)
     home_page = create(:page, website: website)
 
-    login_as(organizer)
+    signin_as(organizer)
     visit edit_event_staff_website_path(event)
     click_on("Add Content")
     fill_in_codemirror(<<~HTML
@@ -111,7 +111,7 @@
     visit page_path(event, home_page)
     expect(response_headers["Cache-Control"]).to eq("max-age=0, private, s-maxage=0")
 
-    login_as(organizer)
+    signin_as(organizer)
     visit edit_event_staff_website_path(event)
 
     select("automatic", from: "Caching")
@@ -126,7 +126,6 @@
     expect(response_headers["Last-Modified"]).to eq(last_modified)
 
     RSpec::Mocks.space.proxy_for(fastly_service).reset
-    sleep 1
     visit event_staff_pages_path(event)
     click_on("Publish")
     expect(fastly_service).to have_received(:purge_by_key).with(event.slug)
@@ -145,7 +144,6 @@
     last_modified = response_headers["Last-Modified"]
 
     RSpec::Mocks.space.proxy_for(fastly_service).reset
-    sleep 1
     visit event_staff_pages_path(event)
     click_on("Publish")
     expect(fastly_service).not_to have_received(:purge_by_key).with(event.slug)
diff --git a/spec/features/website/page_management_spec.rb b/spec/features/website/page_management_spec.rb
index ac2076510..f65477e0b 100644
--- a/spec/features/website/page_management_spec.rb
+++ b/spec/features/website/page_management_spec.rb
@@ -60,7 +60,7 @@
 
   scenario "Organizer publishes a website page", :js do
     home_page = create(:page, unpublished_body: 'Home Content', published_body: nil)
-    login_as(organizer)
+    signin_as(organizer)
 
     visit page_path(slug: event.slug, page: home_page.slug)
     expect(page).to have_content("Page Not Found")
@@ -91,7 +91,7 @@
   end
 
   scenario "Organizer creates and publishes a splash page from a template", :js do
-    login_as(organizer)
+    signin_as(organizer)
     visit new_event_staff_page_path(event)
     select("splash", from: "template")
 
diff --git a/spec/rails_helper.rb b/spec/rails_helper.rb
index 692c78f28..a43f3ee59 100644
--- a/spec/rails_helper.rb
+++ b/spec/rails_helper.rb
@@ -93,3 +93,4 @@ def save_timestamped_screenshot(page)
 
   page.save_screenshot(screenshot_path)
 end
+Capybara.default_max_wait_time = 3.seconds
diff --git a/spec/support/helpers/session_helpers.rb b/spec/support/helpers/session_helpers.rb
index 98b9250c9..b86a2d578 100644
--- a/spec/support/helpers/session_helpers.rb
+++ b/spec/support/helpers/session_helpers.rb
@@ -22,5 +22,8 @@ def forgot_password(email)
       click_button 'Send me reset password instructions'
     end
 
+    def signin_as(user)
+      signin(user.email, user.password)
+    end
   end
 end