diff --git a/Gemfile b/Gemfile
index b94b5a131..ed351306e 100644
--- a/Gemfile
+++ b/Gemfile
@@ -29,6 +29,9 @@ gem "will_paginate", "~> 3.1.7"
 # gem "ckeditor", "~> 4.3.0" # removed given gh security scan results. still need a replacement.
 gem "image_processing"
 
+# Bundle a callout's attached documents into a single downloadable zip
+gem "rubyzip", require: "zip"
+
 # Visit and event tracking
 gem "ahoy_matey"
 # To give group_by_day and similar methods to ActiveRecord relations
diff --git a/Gemfile.lock b/Gemfile.lock
index 076112146..f90fde0bd 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -824,6 +824,7 @@ DEPENDENCIES
   rails (~> 8.1.0)
   rspec-rails
   rubocop-rails-omakase
+  rubyzip
   search_cop
   selenium-webdriver
   shoulda-matchers
diff --git a/app/controllers/events/callouts_controller.rb b/app/controllers/events/callouts_controller.rb
index 056f94e3d..b9f6140e0 100644
--- a/app/controllers/events/callouts_controller.rb
+++ b/app/controllers/events/callouts_controller.rb
@@ -150,6 +150,7 @@ def handouts
       return redirect_to registration_ticket_path(@event_registration.slug) unless builtin_published?("handouts")
       callout = @event.registration_ticket_callouts.find_by(builtin_key: "handouts")
       @handout_cards = resource_cards_for(callout, icon: "fa-solid fa-file-pdf", return_to: "handouts")
+      @download_all_url = download_all_url_for(callout)
     end
 
     # Registrant-facing page for a single Resource, shown in the shared callout
@@ -178,6 +179,17 @@ def faq
       @faq_content = callout&.description.presence || BuiltinCallouts.faq_html
     end
 
+    # Streams every attached document on a callout as a single zip (the "Download
+    # all" button). Payment is excluded — it manages its own documents — and a
+    # callout with fewer than two files 404s, since the button only shows past one.
+    def download_all
+      callout = @event.registration_ticket_callouts.find_by(builtin_key: params[:builtin_key])
+      resources = callout && callout.builtin_key != "payment" ? downloadable_resources(callout) : []
+      raise ActiveRecord::RecordNotFound if resources.size < 2
+      send_data build_documents_zip(resources),
+        filename: documents_zip_filename(callout), type: "application/zip"
+    end
+
     private
 
     # Whether the event's built-in callout for this key is materialized and
@@ -228,6 +240,7 @@ def set_builtin_content
       @builtin_intro = callout&.description.presence
       callout = nil if action_name == "payment"
       @builtin_resource_cards = resource_cards_for(callout, icon: "fa-solid fa-file-lines", return_to: action_name)
+      @download_all_url = download_all_url_for(callout)
     end
 
     # This registrant's cards for a callout's linked resources (nil callout → none).
@@ -239,6 +252,57 @@ def resource_cards_for(callout, icon:, return_to:)
       callout.decorate.resource_cards(registrant_slug: @event_registration.slug, return_to:, icon:)
     end
 
+    # The zip endpoint for a callout's attached documents, or nil when the button
+    # shouldn't show. Backs the "Download all" button the shared callout chrome
+    # renders whenever a page has more than one downloadable resource (handouts and
+    # any built-in callout with attachments — Payment passes a nil callout here, so
+    # its own invoice/receipt/W-9 documents are excluded). Hidden in the sample
+    # preview, whose sentinel slug wouldn't resolve at the zip endpoint.
+    def download_all_url_for(callout)
+      return if callout.nil? || sample_preview?
+      return unless downloadable_resources(callout).many?
+      registration_download_all_path(@event_registration.slug, callout.builtin_key)
+    end
+
+    # A callout's linked resources that carry an attached file, in display order.
+    def downloadable_resources(callout)
+      callout.registration_ticket_callout_resources.ordered
+             .includes(resource: { downloadable_asset: :file_attachment })
+             .filter_map(&:resource)
+             .select { |resource| resource.downloadable_asset&.file&.attached? }
+    end
+
+    # Builds an in-memory zip of the resources' files, named by resource title and
+    # de-duped so two documents sharing a title don't collide inside the archive.
+    def build_documents_zip(resources)
+      used = Set.new
+      Zip::OutputStream.write_buffer do |zip|
+        resources.each do |resource|
+          file = resource.downloadable_asset.file
+          zip.put_next_entry(unique_entry_name(resource, file, used))
+          zip.write(file.download)
+        end
+      end.string
+    end
+
+    def unique_entry_name(resource, file, used)
+      base = resource.title.to_s.strip.gsub(%r{[/\\]}, "-").presence || "document"
+      ext = File.extname(file.filename.to_s)
+      name = "#{base}#{ext}"
+      index = 1
+      while used.include?(name.downcase)
+        index += 1
+        name = "#{base} (#{index})#{ext}"
+      end
+      used << name.downcase
+      name
+    end
+
+    def documents_zip_filename(callout)
+      base = callout.title.presence || callout.builtin_key.humanize
+      "#{base.parameterize}-documents.zip"
+    end
+
     # The join row for @resource on the callout the registrant arrived from
     # (via return_to / callout_id), so the resource page can show that callout's
     # editable page content under the title.
diff --git a/app/views/events/callouts/_callout_page.html.erb b/app/views/events/callouts/_callout_page.html.erb
index 983defbb5..272dde551 100644
--- a/app/views/events/callouts/_callout_page.html.erb
+++ b/app/views/events/callouts/_callout_page.html.erb
@@ -30,6 +30,13 @@
           <h1 class="text-xl font-semibold tracking-wide leading-tight"><%= title %></h1>
           <p class="text-sm text-blue-200"><%= @event.title %></p>
         </div>
+        <%# Download every attached document on this page as one zip. The controller
+            sets @download_all_url only when there's more than one downloadable
+            resource — a single document is grabbed from its own card — and never for
+            Payment, which manages its own invoice/receipt/W-9 documents. %>
+        <% if @download_all_url %>
+          <div class="shrink-0"><%= render "events/callouts/download_all_button", url: @download_all_url %></div>
+        <% end %>
       </div>
       <div class="absolute inset-x-0 bottom-0 h-1 bg-gradient-to-r from-accent via-amber-400 to-accent"></div>
     </div>
diff --git a/app/views/events/callouts/_download_all_button.html.erb b/app/views/events/callouts/_download_all_button.html.erb
new file mode 100644
index 000000000..794f83b58
--- /dev/null
+++ b/app/views/events/callouts/_download_all_button.html.erb
@@ -0,0 +1,7 @@
+<%# "Download all" header action for a callout page: a plain link to the callout's
+    documents.zip endpoint (see CalloutsController#download_all), which bundles every
+    attached document into one archive. url is the zip path. %>
+<%= link_to url, class: "inline-flex items-center gap-2 rounded-lg bg-white/15 px-3 py-1.5 text-sm font-medium text-white ring-1 ring-inset ring-white/30 hover:bg-white/25 transition-colors" do %>
+  <i class="fa-solid fa-download"></i>
+  <span class="hidden sm:inline">Download all</span>
+<% end %>
diff --git a/config/routes.rb b/config/routes.rb
index f1641c215..d55bbf514 100644
--- a/config/routes.rb
+++ b/config/routes.rb
@@ -91,6 +91,7 @@
   get "registration/:slug/handouts", to: "events/callouts#handouts", as: :registration_handouts
   get "registration/:slug/resource/:resource_id", to: "events/callouts#resource", as: :registration_resource
   get "registration/:slug/videoconference", to: "events/callouts#videoconference", as: :registration_videoconference
+  get "registration/:slug/:builtin_key/documents.zip", to: "events/callouts#download_all", as: :registration_download_all
   post "registration/:slug/resend_confirmation", to: "events/registrations#resend_confirmation", as: :registration_resend_confirmation
   post "registration/:slug/cancel", to: "events/registrations#cancel", as: :registration_cancel
   post "registration/:slug/reactivate", to: "events/registrations#reactivate", as: :registration_reactivate
diff --git a/spec/requests/events/callouts_spec.rb b/spec/requests/events/callouts_spec.rb
index ba6818a9f..e744e8933 100644
--- a/spec/requests/events/callouts_spec.rb
+++ b/spec/requests/events/callouts_spec.rb
@@ -91,6 +91,96 @@
     end
   end
 
+  # A single "Download all" header button bundles every attached document on the
+  # page into one zip. It appears on any callout page with more than one
+  # downloadable resource, except Payment (which manages its own W-9/invoice).
+  describe "the Download all button and its zip endpoint" do
+    def attach_resource_to(callout, title)
+      resource = create(:resource, title:)
+      create(:registration_ticket_callout_resource, registration_ticket_callout: callout, resource:)
+      create(:downloadable_asset, owner: resource)
+      resource
+    end
+
+    describe "button visibility on the callout page" do
+      let(:callout) { create(:registration_ticket_callout, event:, builtin_key: "handouts", hidden: false) }
+
+      it "links to the documents zip when there's more than one attached resource" do
+        attach_resource_to(callout, "Aha Moments")
+        attach_resource_to(callout, "AWBW Training Workshop Worksheets")
+
+        get registration_handouts_path(registration.slug)
+
+        expect(response.body).to include(registration_download_all_path(registration.slug, "handouts"))
+      end
+
+      it "is omitted when only one resource carries an attached file" do
+        attach_resource_to(callout, "Aha Moments")
+
+        get registration_handouts_path(registration.slug)
+
+        expect(response.body).not_to include("documents.zip")
+      end
+
+      it "is omitted when no linked resource carries an attached file" do
+        resource = create(:resource, title: "Aha Moments")
+        create(:registration_ticket_callout_resource, registration_ticket_callout: callout, resource:)
+
+        get registration_handouts_path(registration.slug)
+
+        expect(response.body).not_to include("documents.zip")
+      end
+
+      it "never shows on the payment page, even with downloadable documents linked" do
+        paid = create(:event, cost_cents: 10_000)
+        paid_reg = create(:event_registration, event: paid)
+        payment = create(:registration_ticket_callout, event: paid, builtin_key: "payment")
+        attach_resource_to(payment, "W-9")
+        attach_resource_to(payment, "Terms")
+
+        get registration_payment_path(paid_reg.slug)
+
+        expect(response.body).not_to include("documents.zip")
+      end
+    end
+
+    describe "GET /registration/:slug/:builtin_key/documents.zip" do
+      let(:callout) { create(:registration_ticket_callout, event:, builtin_key: "handouts", hidden: false) }
+
+      it "streams a zip of every attached document, named by resource title" do
+        attach_resource_to(callout, "Aha Moments")
+        attach_resource_to(callout, "Workshop Worksheets")
+
+        get registration_download_all_path(registration.slug, "handouts")
+
+        expect(response).to have_http_status(:success)
+        expect(response.media_type).to eq("application/zip")
+        entries = Zip::File.open_buffer(response.body).map(&:name)
+        expect(entries).to contain_exactly("Aha Moments.pdf", "Workshop Worksheets.pdf")
+      end
+
+      it "404s when fewer than two documents are attached" do
+        attach_resource_to(callout, "Only One")
+
+        get registration_download_all_path(registration.slug, "handouts")
+
+        expect(response).to have_http_status(:not_found)
+      end
+
+      it "404s for the payment callout" do
+        paid = create(:event, cost_cents: 10_000)
+        paid_reg = create(:event_registration, event: paid)
+        payment = create(:registration_ticket_callout, event: paid, builtin_key: "payment")
+        attach_resource_to(payment, "W-9")
+        attach_resource_to(payment, "Terms")
+
+        get registration_download_all_path(paid_reg.slug, "payment")
+
+        expect(response).to have_http_status(:not_found)
+      end
+    end
+  end
+
   describe "GET /registration/:slug/payment" do
     let(:event) { create(:event, cost_cents: 10_000) }