diff --git a/Gemfile b/Gemfile
index c0bb815f2d36..314c64783da5 100644
--- a/Gemfile
+++ b/Gemfile
@@ -188,7 +188,7 @@ gem 'aws-sdk-core', '~> 3.107'
 # File upload via fog + screenshots on travis
 gem 'aws-sdk-s3', '~> 1.91'
 
-gem 'openproject-token', '~> 3.0.1'
+gem 'openproject-token', '~> 4.0'
 
 gem 'plaintext', '~> 0.3.2'
 
diff --git a/Gemfile.lock b/Gemfile.lock
index 0d29092bf932..eda38d29683a 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -686,7 +686,7 @@ GEM
       activesupport (>= 5.0.0)
       openproject-octicons (>= 19.7.0)
       view_component (>= 3.1, < 4.0)
-    openproject-token (3.0.1)
+    openproject-token (4.0.0)
       activemodel
     os (1.1.4)
     ox (2.14.17)
@@ -1127,7 +1127,7 @@ DEPENDENCIES
   openproject-reporting!
   openproject-storages!
   openproject-team_planner!
-  openproject-token (~> 3.0.1)
+  openproject-token (~> 4.0)
   openproject-two_factor_authentication!
   openproject-webhooks!
   openproject-xls_export!
diff --git a/app/components/work_packages/share/modal_upsale_component.html.erb b/app/components/work_packages/share/modal_upsale_component.html.erb
new file mode 100644
index 000000000000..2d5f3269a0d7
--- /dev/null
+++ b/app/components/work_packages/share/modal_upsale_component.html.erb
@@ -0,0 +1,17 @@
+<%=
+  component_wrapper(tag: 'turbo-frame') do
+    render Primer::Beta::Blankslate.new(border: true) do |component|
+      component.with_visual_icon(icon: :'op-enterprise-addons', classes: 'upsale-colored')
+      component.with_heading(tag: :h2, classes: 'upsale-colored').with_content(I18n.t(:label_enterprise_addon))
+      component.with_description { I18n.t('mail.sharing.work_packages.enterprise_text') }
+
+      href = "#{OpenProject::Static::Links.links[:upsale][:href]}/?utm_source=unknown&utm_medium=community-edition&utm_campaign=work-package-sharing-modal"
+      component.with_secondary_action(href:) do
+        flex_layout(justify_content: :center) do |flex|
+          flex.with_column(mr: 1) { I18n.t("admin.enterprise.enterprise_link") }
+          flex.with_column { render(Primer::Beta::Octicon.new(icon: :'link-external')) }
+        end
+      end
+    end
+  end
+%>
diff --git a/app/components/work_packages/share/modal_upsale_component.rb b/app/components/work_packages/share/modal_upsale_component.rb
new file mode 100644
index 000000000000..498494814fd4
--- /dev/null
+++ b/app/components/work_packages/share/modal_upsale_component.rb
@@ -0,0 +1,41 @@
+#-- copyright
+# OpenProject is an open source project management software.
+# Copyright (C) 2012-2023 the OpenProject GmbH
+#
+# This program is free software; you can redistribute it and/or
+# modify it under the terms of the GNU General Public License version 3.
+#
+# OpenProject is a fork of ChiliProject, which is a fork of Redmine. The copyright follows:
+# Copyright (C) 2006-2013 Jean-Philippe Lang
+# Copyright (C) 2010-2013 the ChiliProject Team
+#
+# This program is free software; you can redistribute it and/or
+# modify it under the terms of the GNU General Public License
+# as published by the Free Software Foundation; either version 2
+# of the License, or (at your option) any later version.
+#
+# This program is distributed in the hope that it will be useful,
+# but WITHOUT ANY WARRANTY; without even the implied warranty of
+# MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+# GNU General Public License for more details.
+#
+# You should have received a copy of the GNU General Public License
+# along with this program; if not, write to the Free Software
+# Foundation, Inc., 51 Franklin Street, Fifth Floor, Boston, MA  02110-1301, USA.
+#
+# See COPYRIGHT and LICENSE files for more details.
+#++
+
+module WorkPackages
+  module Share
+    class ModalUpsaleComponent < ApplicationComponent
+      include ApplicationHelper
+      include OpTurbo::Streamable
+      include OpPrimer::ComponentHelpers
+
+      def self.wrapper_key
+        "work_package_share_list"
+      end
+    end
+  end
+end
diff --git a/app/controllers/work_packages/shares_controller.rb b/app/controllers/work_packages/shares_controller.rb
index 9b54db9928d9..3b399d3e4088 100644
--- a/app/controllers/work_packages/shares_controller.rb
+++ b/app/controllers/work_packages/shares_controller.rb
@@ -34,6 +34,7 @@ class WorkPackages::SharesController < ApplicationController
   before_action :find_share, only: %i[destroy update]
   before_action :find_project
   before_action :authorize
+  before_action :enterprise_check, only: %i[index]
 
   def index
     query = load_query
@@ -52,10 +53,10 @@ def create
 
     find_or_create_users(send_notification: false) do |member_params|
       service_call = WorkPackageMembers::CreateOrUpdateService
-                      .new(user: current_user)
-                      .call(entity: @work_package,
-                            user_id: member_params[:user_id],
-                            role_ids: find_role_ids(params[:member][:role_id]))
+        .new(user: current_user)
+        .call(entity: @work_package,
+              user_id: member_params[:user_id],
+              role_ids: find_role_ids(params[:member][:role_id]))
 
       overall_result.push(service_call)
     end
@@ -95,6 +96,12 @@ def destroy
 
   private
 
+  def enterprise_check
+    return if EnterpriseToken.allows_to?(:work_package_sharing)
+
+    render WorkPackages::Share::ModalUpsaleComponent.new
+  end
+
   def respond_with_replace_modal
     replace_via_turbo_stream(
       component: WorkPackages::Share::ModalBodyComponent.new(work_package: @work_package, shares: @new_shares || find_shares)
@@ -165,10 +172,10 @@ def find_project
 
   def current_visible_member_count
     @current_visible_member_count ||= Member
-                                        .joins(:member_roles)
-                                        .of_work_package(@work_package)
-                                        .merge(MemberRole.only_non_inherited)
-                                        .size
+      .joins(:member_roles)
+      .of_work_package(@work_package)
+      .merge(MemberRole.only_non_inherited)
+      .size
   end
 
   def load_query
diff --git a/app/services/authorization/enterprise_service.rb b/app/services/authorization/enterprise_service.rb
index d6409849329d..f2333fb65ec6 100644
--- a/app/services/authorization/enterprise_service.rb
+++ b/app/services/authorization/enterprise_service.rb
@@ -47,6 +47,7 @@ class Authorization::EnterpriseService
     team_planner_view
     two_factor_authentication
     work_package_query_relation_columns
+    work_package_sharing
   ).freeze
 
   def initialize(token)
diff --git a/app/views/projects/settings/modules/_form.html.erb b/app/views/projects/settings/modules/_form.html.erb
index 40c73c1b7ab6..e4fceb99ccac 100644
--- a/app/views/projects/settings/modules/_form.html.erb
+++ b/app/views/projects/settings/modules/_form.html.erb
@@ -37,7 +37,7 @@ See COPYRIGHT and LICENSE files for more details.
         <%= spot_icon('enterprise-addons',
                       inline: true,
                       size: '1_25',
-                      classnames: 'upsale-icon_highlighted') %>
+                      classnames: 'upsale-colored') %>
       <% end %>
     </label>
     <div class="form--field-container">
diff --git a/config/locales/en.yml b/config/locales/en.yml
index b47f8268a575..3e69e8440657 100644
--- a/config/locales/en.yml
+++ b/config/locales/en.yml
@@ -1858,6 +1858,7 @@ en:
   label_enterprise_active_users: "%{current}/%{limit} booked active users"
   label_enterprise_edition: "Enterprise edition"
   label_enterprise_support: "Enterprise support"
+  label_enterprise_addon: "Enterprise add-on"
   label_environment: "Environment"
   label_estimates_and_time: "Estimates and time"
   label_equals: "is"
@@ -2330,6 +2331,7 @@ en:
         create_account: "To access this work package you will need to create an %{instance} account. "
         open_work_package: "Open work package"
         subject: "You have been shared work package #%{id}"
+        enterprise_text: "Share work packages with users who are not members of the project."
         summary:
           user: "%{user} shared a work package with you with %{role_rights} rights"
           group: "%{user} shared a work package with the group %{group} you are a member of"
diff --git a/frontend/src/global_styles/content/_enterprise.sass b/frontend/src/global_styles/content/_enterprise.sass
index 78631572cfa6..76bc9b1956db 100644
--- a/frontend/src/global_styles/content/_enterprise.sass
+++ b/frontend/src/global_styles/content/_enterprise.sass
@@ -52,9 +52,8 @@
   justify-content: center
   align-items: center
 
-.upsale-icon
-  &_highlighted
-    color: $spot-color-feedback-warning-dark
+.upsale-colored
+  color: $spot-color-feedback-warning-dark
 
 .widget-box--blocks--upsale-title
   font-weight: 400
diff --git a/lib/redmine/menu_manager/menu_helper.rb b/lib/redmine/menu_manager/menu_helper.rb
index ca403b4ae957..8796224a0cd8 100644
--- a/lib/redmine/menu_manager/menu_helper.rb
+++ b/lib/redmine/menu_manager/menu_helper.rb
@@ -229,7 +229,7 @@ def render_single_menu_node(item, project = nil, menu_class = 'op-menu')
                              lang: menu_item_locale(item)) do
       title_text = ''.html_safe + content_tag(:span, caption, class: 'ellipsis') + badge_for(item)
       if item.enterprise_feature.present? && !EnterpriseToken.allows_to?(item.enterprise_feature)
-        title_text << (''.html_safe + spot_icon('enterprise-addons', size: '1_25', classnames: 'upsale-icon_highlighted'))
+        title_text << (''.html_safe + spot_icon('enterprise-addons', size: '1_25', classnames: 'upsale-colored'))
       end
       title_text
     end
diff --git a/spec/features/work_packages/share/bulk_sharing_spec.rb b/spec/features/work_packages/share/bulk_sharing_spec.rb
index 494977c43166..9ebf4ff8cfa0 100644
--- a/spec/features/work_packages/share/bulk_sharing_spec.rb
+++ b/spec/features/work_packages/share/bulk_sharing_spec.rb
@@ -32,6 +32,7 @@
 
 RSpec.describe 'Work Packages', 'Bulk Sharing',
                :js, :with_cuprite,
+               with_ee: %i[work_package_sharing],
                with_flag: { work_package_sharing: true } do
   shared_let(:view_work_package_role)    { create(:view_work_package_role)    }
   shared_let(:comment_work_package_role) { create(:comment_work_package_role) }
diff --git a/spec/features/work_packages/share/enterprise_restriction_spec.rb b/spec/features/work_packages/share/enterprise_restriction_spec.rb
new file mode 100644
index 000000000000..76b1cfccd1d4
--- /dev/null
+++ b/spec/features/work_packages/share/enterprise_restriction_spec.rb
@@ -0,0 +1,73 @@
+# frozen_string_literal: true
+
+# -- copyright
+# OpenProject is an open source project management software.
+# Copyright (C) 2023 the OpenProject GmbH
+#
+# This program is free software; you can redistribute it and/or
+# modify it under the terms of the GNU General Public License version 3.
+#
+# OpenProject is a fork of ChiliProject, which is a fork of Redmine. The copyright follows:
+# Copyright (C) 2006-2013 Jean-Philippe Lang
+# Copyright (C) 2010-2013 the ChiliProject Team
+#
+# This program is free software; you can redistribute it and/or
+# modify it under the terms of the GNU General Public License
+# as published by the Free Software Foundation; either version 2
+# of the License, or (at your option) any later version.
+#
+# This program is distributed in the hope that it will be useful,
+# but WITHOUT ANY WARRANTY; without even the implied warranty of
+# MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+# GNU General Public License for more details.
+#
+# You should have received a copy of the GNU General Public License
+# along with this program; if not, write to the Free Software
+# Foundation, Inc., 51 Franklin Street, Fifth Floor, Boston, MA  02110-1301, USA.
+#
+# See COPYRIGHT and LICENSE files for more details.
+# ++
+
+require 'rails_helper'
+
+RSpec.describe 'Work Package Sharing Enterprise Restriction',
+               :js, :with_cuprite,
+               with_flag: { work_package_sharing: true } do
+  shared_let(:view_work_package_role)    { create(:view_work_package_role)    }
+  shared_let(:comment_work_package_role) { create(:comment_work_package_role) }
+  shared_let(:edit_work_package_role)    { create(:edit_work_package_role)    }
+
+  shared_let(:sharer_role) do
+    create(:project_role, permissions: %i[view_work_packages
+                                          view_shared_work_packages
+                                          share_work_packages])
+  end
+
+  shared_let(:sharer) { create(:user, firstname: 'Sharer', lastname: 'User') }
+
+  shared_let(:project)      { create(:project, members: { sharer => [sharer_role] }) }
+  shared_let(:work_package) { create(:work_package, project:) }
+
+  let(:work_package_page) { Pages::FullWorkPackage.new(work_package)               }
+  let(:share_modal)       { Components::WorkPackages::ShareModal.new(work_package) }
+
+  current_user { sharer }
+
+  before do
+    work_package_page.visit!
+    click_button 'Share'
+    share_modal.expect_open
+  end
+
+  context 'without an enterprise token' do
+    it 'renders an upsale banner' do
+      share_modal.expect_upsale_banner
+    end
+  end
+
+  context 'with an enterprise token', with_ee: %i[work_package_sharing] do
+    it 'renders the share modal' do
+      share_modal.expect_blankslate
+    end
+  end
+end
diff --git a/spec/features/work_packages/share/filter_spec.rb b/spec/features/work_packages/share/filter_spec.rb
index 253d3f5470eb..7f4094f166c0 100644
--- a/spec/features/work_packages/share/filter_spec.rb
+++ b/spec/features/work_packages/share/filter_spec.rb
@@ -31,8 +31,8 @@
 require 'spec_helper'
 
 RSpec.describe 'Work package sharing',
-               :js,
-               :with_cuprite,
+               :js, :with_cuprite,
+               with_ee: %i[work_package_sharing],
                with_flag: { work_package_sharing: true } do
   shared_let(:view_work_package_role) { create(:view_work_package_role) }
   shared_let(:comment_work_package_role) { create(:comment_work_package_role) }
diff --git a/spec/features/work_packages/share/multi_invite_spec.rb b/spec/features/work_packages/share/multi_invite_spec.rb
index 095c6ac2d39e..7aaca0d74ec3 100644
--- a/spec/features/work_packages/share/multi_invite_spec.rb
+++ b/spec/features/work_packages/share/multi_invite_spec.rb
@@ -31,8 +31,8 @@
 require 'spec_helper'
 
 RSpec.describe 'Work package sharing',
-               :js,
-               :with_cuprite,
+               :js, :with_cuprite,
+               with_ee: %i[work_package_sharing],
                with_flag: { work_package_sharing: true } do
   shared_let(:view_work_package_role) { create(:view_work_package_role) }
   shared_let(:comment_work_package_role) { create(:comment_work_package_role) }
diff --git a/spec/features/work_packages/share_spec.rb b/spec/features/work_packages/share_spec.rb
index 5e23d61e0f54..010ff5ae340a 100644
--- a/spec/features/work_packages/share_spec.rb
+++ b/spec/features/work_packages/share_spec.rb
@@ -31,8 +31,8 @@
 require 'spec_helper'
 
 RSpec.describe 'Work package sharing',
-               :js,
-               :with_cuprite,
+               :js, :with_cuprite,
+               with_ee: %i[work_package_sharing],
                with_flag: { work_package_sharing: true } do
   shared_let(:view_work_package_role) { create(:view_work_package_role) }
   shared_let(:comment_work_package_role) { create(:comment_work_package_role) }
diff --git a/spec/support/components/work_packages/share_modal.rb b/spec/support/components/work_packages/share_modal.rb
index d8ef2741e02a..3bda399e64b1 100644
--- a/spec/support/components/work_packages/share_modal.rb
+++ b/spec/support/components/work_packages/share_modal.rb
@@ -234,7 +234,9 @@ def change_role(user, role_name)
         within user_row(user) do
           find('[data-test-selector="op-share-wp-update-role"]').click
 
-          find('.ActionListContent', text: role_name).click
+          within '.ActionListWrap' do
+            click_button role_name
+          end
         end
       end
 
@@ -338,6 +340,13 @@ def select_not_existing_user_option(email)
                             select_text: "Send invite to\"#{email}\"",
                             results_selector: 'body'
       end
+
+      def expect_upsale_banner
+        within modal_element do
+          expect(page)
+            .to have_text(I18n.t(:label_enterprise_addon))
+        end
+      end
     end
   end
 end