diff --git a/app/components/enterprise_edition/banner_component.rb b/app/components/enterprise_edition/banner_component.rb
index 9f778e107d2..80be876e196 100644
--- a/app/components/enterprise_edition/banner_component.rb
+++ b/app/components/enterprise_edition/banner_component.rb
@@ -44,7 +44,7 @@ module EnterpriseEdition
     VARIANT_OPTIONS = %i[inline medium large].freeze
 
     # @param feature_key [Symbol, NilClass] The key of the feature to show the banner for.
-    # @param variant [Symbol, NilClass] The variant of the banner comopnent.
+    # @param variant [Symbol, NilClass] The variant of the banner component.
     # @param image [String, NilClass] Path to the image to show on the banner, or nil.
     #   Only applicable and required when variant is :medium.
     # @param video [String, NilClass] Path to the video to show on the banner, or nil.
@@ -55,7 +55,7 @@ module EnterpriseEdition
     # @param show_always [boolean] Always show the banner, regardless of the dismissed or feature state.
     # @param dismiss_key [String] Provide a string to identify this banner when being dismissed. Defaults to feature_key
     # @param system_arguments [Hash] <%= link_to_system_arguments_docs %>
-    def initialize(feature_key, # rubocop:disable Metrics/AbcSize
+    def initialize(feature_key,
                    variant: DEFAULT_VARIANT,
                    image: nil,
                    video: nil,
@@ -68,12 +68,15 @@ module EnterpriseEdition
       @image = image
       @video = video
       @dismissable = dismissable
-      @dismiss_key = dismiss_key
+      @dismiss_key = dismiss_key.to_s
+
       @show_always = show_always
 
       self.feature_key = feature_key
       self.i18n_scope = i18n_scope
 
+      trial_overrides! if trial_feature?
+
       if @variant == :medium && @image.nil?
         raise ArgumentError, "The 'image' parameter is required when the variant is :medium."
       end
@@ -82,17 +85,7 @@ module EnterpriseEdition
         raise ArgumentError, "The 'video' parameter is required when the variant is :large."
       end
 
-      @system_arguments = system_arguments
-      @system_arguments[:tag] = :div
-      @system_arguments[:mb] ||= 2
-      @system_arguments[:id] = "op-enterprise-banner-#{feature_key.to_s.tr('_', '-')}"
-      @system_arguments[:test_selector] = "op-enterprise-banner"
-      @system_arguments[:classes] = class_names(
-        @system_arguments[:classes],
-        "op-enterprise-banner",
-        @variant == :medium ? "op-enterprise-banner_medium" : nil,
-        @variant == :large ? "op-enterprise-banner_large" : nil
-      )
+      set_system_arguments(system_arguments, feature_key)
 
       super
     end
@@ -115,15 +108,39 @@ module EnterpriseEdition
     end
 
     def wrapper_key
-      "enterprise_banner_#{feature_key}"
+      "enterprise_banner_#{@dismiss_key}"
     end
 
     private
 
+    def set_system_arguments(system_arguments, feature_key)
+      @system_arguments = system_arguments
+      @system_arguments[:tag] = :div
+      @system_arguments[:mb] ||= 2
+      @system_arguments[:id] = "op-enterprise-banner-#{feature_key.to_s.tr('_', '-')}"
+      @system_arguments[:test_selector] = "op-enterprise-banner"
+      @system_arguments[:classes] = class_names(
+        @system_arguments[:classes],
+        "op-enterprise-banner",
+        "op-enterprise-banner_medium" => @variant == :medium,
+        "op-enterprise-banner_large" => @variant == :large,
+        "op-enterprise-banner_trial" => trial_feature?
+      )
+    end
+
+    def trial_overrides!
+      @dismissable = true
+      @dismiss_key += "_trial" unless @dismiss_key.end_with?("_trial")
+      @variant = :inline
+    end
+
     def render?
       return true if @show_always
+      return false if dismissed?
+      return true if feature_available? && trial_feature?
+      return false if EnterpriseToken.hide_banners?
 
-      !(EnterpriseToken.hide_banners? || feature_available? || dismissed?)
+      !feature_available?
     end
 
     def feature_available?
@@ -135,5 +152,9 @@ module EnterpriseEdition
 
       User.current.pref.dismissed_banner?(@dismiss_key)
     end
+
+    def trial_feature?
+      EnterpriseToken.trialling?(feature_key)
+    end
   end
 end
diff --git a/app/components/enterprise_edition/upsell_buttons_component.rb b/app/components/enterprise_edition/upsell_buttons_component.rb
index 2eaf28d164b..82cce0f45cf 100644
--- a/app/components/enterprise_edition/upsell_buttons_component.rb
+++ b/app/components/enterprise_edition/upsell_buttons_component.rb
@@ -58,6 +58,7 @@ module EnterpriseEdition
 
     def buttons
       [
+        buy_now_button,
         free_trial_button,
         upgrade_now_button,
         more_info_button
@@ -74,6 +75,20 @@ module EnterpriseEdition
       )
     end
 
+    def buy_now_button
+      return unless EnterpriseToken.active?
+      return unless User.current.admin?
+
+      render(Primer::Beta::Button.new(
+               classes: "upsell-colored-background",
+               tag: :a,
+               href: OpenProject::Enterprise.upgrade_path,
+               align_self: :center
+             )) do
+        I18n.t("ee.upsell.buy_now_button")
+      end
+    end
+
     # Allow providing a custom upgrade now button
     def upgrade_now_button
       nil
diff --git a/app/components/settings/project_life_cycle_step_definitions/index_component.html.erb b/app/components/settings/project_life_cycle_step_definitions/index_component.html.erb
index e6a8145822c..93bfb3498fb 100644
--- a/app/components/settings/project_life_cycle_step_definitions/index_component.html.erb
+++ b/app/components/settings/project_life_cycle_step_definitions/index_component.html.erb
@@ -31,7 +31,14 @@ See COPYRIGHT and LICENSE files for more details.
   component_wrapper do
     flex_layout(data: wrapper_data_attributes) do |flex|
       flex.with_row do
-        if allowed_to_customize_life_cycle?
+        render EnterpriseEdition::BannerComponent.new(:customize_life_cycle,
+                                                      variant: :medium,
+                                                      image: "enterprise/project-lifecycle.png",
+                                                      mb: 3)
+      end
+
+      if allowed_to_customize_life_cycle?
+        flex.with_row do
           render(Primer::OpenProject::SubHeader.new) do |subheader|
             subheader.with_filter_input(
               name: "border-box-filter",
@@ -57,11 +64,6 @@ See COPYRIGHT and LICENSE files for more details.
               I18n.t("settings.project_phase_definitions.label_add")
             end
           end
-        else
-          render EnterpriseEdition::BannerComponent.new(:customize_life_cycle,
-                                                        variant: :medium,
-                                                        image: "enterprise/project-lifecycle.png",
-                                                        mb: 3)
         end
       end
 
diff --git a/app/components/shares/modal_body_component.html.erb b/app/components/shares/modal_body_component.html.erb
index 3bc42afca95..7612091818c 100644
--- a/app/components/shares/modal_body_component.html.erb
+++ b/app/components/shares/modal_body_component.html.erb
@@ -7,7 +7,8 @@
         end
       end
 
-      render(strategy.manage_shares_component(modal_content:, errors:))
+      render(strategy.upsell_banner(modal_content:))
+      render(strategy.manage_shares_component(modal_content:, errors:)) if strategy.allow_feature?
     end
   end
 %>
diff --git a/app/components/shares/work_packages/modal_upsell_component.html.erb b/app/components/shares/work_packages/modal_upsell_component.html.erb
index b283aba4e06..f10285902d1 100644
--- a/app/components/shares/work_packages/modal_upsell_component.html.erb
+++ b/app/components/shares/work_packages/modal_upsell_component.html.erb
@@ -1,5 +1,7 @@
 <%=
   component_wrapper(tag: "turbo-frame") do
-    render(EnterpriseEdition::BannerComponent.new(:work_package_sharing))
+    modal_content.with_row do
+      render(EnterpriseEdition::BannerComponent.new(:work_package_sharing))
+    end
   end
 %>
diff --git a/app/components/shares/work_packages/modal_upsell_component.rb b/app/components/shares/work_packages/modal_upsell_component.rb
index 3b9efbb5a81..a26e98f422c 100644
--- a/app/components/shares/work_packages/modal_upsell_component.rb
+++ b/app/components/shares/work_packages/modal_upsell_component.rb
@@ -33,6 +33,14 @@ module Shares
       include OpTurbo::Streamable
       include OpPrimer::ComponentHelpers
 
+      def initialize(modal_content:)
+        super
+
+        @modal_content = modal_content
+      end
+
+      attr_reader :modal_content
+
       def self.wrapper_key
         "share_modal_body"
       end
diff --git a/app/controllers/my/enterprise_banners_controller.rb b/app/controllers/my/enterprise_banners_controller.rb
index e627b18ae77..c9cca555a87 100644
--- a/app/controllers/my/enterprise_banners_controller.rb
+++ b/app/controllers/my/enterprise_banners_controller.rb
@@ -47,9 +47,13 @@ class My::EnterpriseBannersController < ApplicationController
 
   def dismiss
     pref = User.current.pref
-    pref.dismiss_banner(@feature_key)
+    pref.dismiss_banner(@dismiss_key)
     if pref.save
-      remove_via_turbo_stream(component: EnterpriseEdition::BannerComponent.new(@feature_key))
+      remove_via_turbo_stream(component: EnterpriseEdition::BannerComponent.new(
+        @feature_key,
+        dismiss_key: @dismiss_key,
+        show_always: true
+      ))
       respond_with_turbo_streams
     else
       respond_with_flash_error(message: call.message)
@@ -59,7 +63,11 @@ class My::EnterpriseBannersController < ApplicationController
   private
 
   def get_feature_key
-    @feature_key = params[:feature_key].to_sym
+    raw_key = params[:feature_key]
+
+    @dismiss_key = raw_key
+    @feature_key = raw_key.gsub(/_trial$/, "").to_sym
+
     render_400 unless OpenProject::Token.lowest_plan_for(@feature_key)
   end
 end
diff --git a/app/forms/statuses/form.rb b/app/forms/statuses/form.rb
index 2948f1356aa..cac0631dde9 100644
--- a/app/forms/statuses/form.rb
+++ b/app/forms/statuses/form.rb
@@ -86,10 +86,8 @@ module Statuses
         }
       )
 
-      if readonly_work_packages_restricted?
-        statuses_form.html_content do
-          render(EnterpriseEdition::BannerComponent.new(:readonly_work_packages))
-        end
+      statuses_form.html_content do
+        render(EnterpriseEdition::BannerComponent.new(:readonly_work_packages))
       end
 
       statuses_form.check_box(
diff --git a/app/models/enterprise_token.rb b/app/models/enterprise_token.rb
index 2dcad4af441..e5559fb4a5f 100644
--- a/app/models/enterprise_token.rb
+++ b/app/models/enterprise_token.rb
@@ -45,6 +45,18 @@ class EnterpriseToken < ApplicationRecord
       current && !current.expired?
     end
 
+    def available_features
+      EnterpriseToken.current&.available_features || []
+    end
+
+    def trialling_features
+      available_features.select { |feature| trialling?(feature) }
+    end
+
+    def trialling?(feature)
+      allows_to?(feature) && EnterpriseToken.current.trial?
+    end
+
     def hide_banners?
       OpenProject::Configuration.ee_hide_banners?
     end
@@ -88,6 +100,7 @@ class EnterpriseToken < ApplicationRecord
            :plan,
            :features,
            :version,
+           :trial?,
            to: :token_object
 
   def token_object
diff --git a/app/models/sharing_strategies/project_query_strategy.rb b/app/models/sharing_strategies/project_query_strategy.rb
index 9ee3c9922e1..cd30bb88804 100644
--- a/app/models/sharing_strategies/project_query_strategy.rb
+++ b/app/models/sharing_strategies/project_query_strategy.rb
@@ -105,18 +105,19 @@ module SharingStrategies
       end
     end
 
-    def manage_shares_component(modal_content:, errors:)
-      if EnterpriseToken.allows_to?(:project_list_sharing)
-        super
-      else
-        Shares::ProjectQueries::UpsellComponent.new(modal_content:)
-      end
-    end
-
     def title
       I18n.t(:label_share_project_list)
     end
 
+    def upsell_banner(modal_content:)
+      Shares::ProjectQueries::UpsellComponent.new(modal_content:)
+    end
+
+    def allow_feature?
+      EnterpriseToken.allows_to?(:project_list_sharing) ||
+        EnterpriseToken.trialling?(:project_list_sharing)
+    end
+
     private
 
     def virtual_owner_share
diff --git a/app/models/sharing_strategies/work_package_strategy.rb b/app/models/sharing_strategies/work_package_strategy.rb
index d51c3be999f..e398663d0e9 100644
--- a/app/models/sharing_strategies/work_package_strategy.rb
+++ b/app/models/sharing_strategies/work_package_strategy.rb
@@ -99,18 +99,19 @@ module SharingStrategies
       Shares::WorkPackages::DeleteContract
     end
 
-    def modal_body_component(errors)
-      if EnterpriseToken.allows_to?(:work_package_sharing)
-        super
-      else
-        Shares::WorkPackages::ModalUpsellComponent.new
-      end
-    end
-
     def title
       I18n.t(:label_share_work_package)
     end
 
+    def upsell_banner(modal_content:)
+      Shares::WorkPackages::ModalUpsellComponent.new(modal_content:)
+    end
+
+    def allow_feature?
+      EnterpriseToken.allows_to?(:work_package_sharing) ||
+        EnterpriseToken.trialling?(:work_package_sharing)
+    end
+
     private
 
     def project_member?(share)
diff --git a/app/views/custom_fields/new.html.erb b/app/views/custom_fields/new.html.erb
index 448c0fba16d..aac6a2f74dc 100644
--- a/app/views/custom_fields/new.html.erb
+++ b/app/views/custom_fields/new.html.erb
@@ -46,7 +46,7 @@ See COPYRIGHT and LICENSE files for more details.
 <% content_controller "admin--custom-fields",
                       dynamic: true,
                       "admin--custom-fields-format-config-value": OpenProject::CustomFieldFormatDependent.stimulus_config,
-                      "admin--custom-fields-enterprise-edition-value": EnterpriseToken.allows_to?(:custom_field_hierarchies) %>
+                      "admin--custom-fields-hierarchy-enabled-value": EnterpriseToken.allows_to?(:custom_field_hierarchies) %>
 
 <%= labelled_tabular_form_for @custom_field, as: :custom_field,
                                              url: custom_fields_path,
diff --git a/config/locales/en.yml b/config/locales/en.yml
index 808db78226d..e5c4f80ca85 100644
--- a/config/locales/en.yml
+++ b/config/locales/en.yml
@@ -2094,12 +2094,12 @@ en:
       readonly_work_packages: Readonly Work Packages
       sso_auth_providers: Single sign-on
       team_planner_view: Team Planner View
-      two_factor_authentication: 2FA Authentication
       virus_scanning: Antivirus Scanning
       work_package_query_relation_columns: Work Package Query Relation Columns
       work_package_sharing: Share work packages with external users
       work_package_subject_generation: Work Package Subject Generation
     upsell:
+      buy_now_button: "Buy now"
       plans_title: "Enterprise plans"
       title: "Enterprise add-on"
       plan_title: "Enterprise %{plan} add-on"
diff --git a/frontend/src/app/core/config/configuration.service.ts b/frontend/src/app/core/config/configuration.service.ts
index 027a23cc87a..071ac782ae0 100644
--- a/frontend/src/app/core/config/configuration.service.ts
+++ b/frontend/src/app/core/config/configuration.service.ts
@@ -150,6 +150,10 @@ export class ConfigurationService {
     return this.systemPreference<string[]>('availableFeatures');
   }
 
+  public get triallingFeatures():string[] {
+    return this.systemPreference<string[]>('triallingFeatures');
+  }
+
   private loadConfiguration() {
     return this
       .apiV3Service
diff --git a/frontend/src/app/core/enterprise/banners.service.ts b/frontend/src/app/core/enterprise/banners.service.ts
index 4a74e35158d..9912d212b01 100644
--- a/frontend/src/app/core/enterprise/banners.service.ts
+++ b/frontend/src/app/core/enterprise/banners.service.ts
@@ -43,7 +43,19 @@ export class BannersService {
   }
 
   public showBannerFor(feature:string):boolean {
-    return !(this._bannersHidden || this.configuration.availableFeatures.includes(feature));
+    if (this._bannersHidden) {
+      return false;
+    }
+
+    return !this.allowsTo(feature) || this.trialling(feature);
+  }
+
+  public allowsTo(feature:string):boolean {
+    return this.configuration.availableFeatures.includes(feature);
+  }
+
+  public trialling(feature:string):boolean {
+    return this.configuration.triallingFeatures.includes(feature);
   }
 
   public getEnterPriseEditionUrl({ referrer, hash }:{ referrer?:string, hash?:string } = {}) {
@@ -59,13 +71,13 @@ export class BannersService {
     return url.toString();
   }
 
-  public async conditional(feature:string, bannersVisible?:() => void, bannersNotVisible?:() => void) {
+  public async conditional(feature:string, featureNotAvailable?:() => void, featureAvailable?:() => void) {
     await this.configuration.initialize();
 
-    if (this.showBannerFor(feature)) {
-      this.callMaybe(bannersVisible);
+    if (this.allowsTo(feature)) {
+      this.callMaybe(featureAvailable);
     } else {
-      this.callMaybe(bannersNotVisible);
+      this.callMaybe(featureNotAvailable);
     }
   }
 
diff --git a/frontend/src/app/features/admin/types/type-banner.service.ts b/frontend/src/app/features/admin/types/type-banner.service.ts
index 18a355a5af0..3d5937bf2d7 100644
--- a/frontend/src/app/features/admin/types/type-banner.service.ts
+++ b/frontend/src/app/features/admin/types/type-banner.service.ts
@@ -7,7 +7,7 @@ import { ConfigurationService } from 'core-app/core/config/configuration.service
 
 @Injectable()
 export class TypeBannerService extends BannersService {
-  showBanners = this.showBannerFor('edit_attribute_groups');
+  eeAvailable = this.allowsTo('edit_attribute_groups');
 
   constructor(
     @Inject(DOCUMENT) protected documentElement:Document,
diff --git a/frontend/src/app/features/admin/types/type-form-configuration.html b/frontend/src/app/features/admin/types/type-form-configuration.html
index ef1ca845855..2fd43ea8544 100644
--- a/frontend/src/app/features/admin/types/type-form-configuration.html
+++ b/frontend/src/app/features/admin/types/type-form-configuration.html
@@ -10,7 +10,7 @@
         </button>
       </li>
       <li
-        *ngIf="!typeBanner.showBanners"
+        *ngIf="typeBanner.eeAvailable"
         class="toolbar-item drop-down">
         <a class="form-configuration--add-group button -primary" aria-haspopup="true">
           <op-icon icon-classes="button--icon icon-add"></op-icon>
diff --git a/frontend/src/app/features/boards/board/board-actions/board-actions-registry.service.ts b/frontend/src/app/features/boards/board/board-actions/board-actions-registry.service.ts
index fb22c325ef0..c30424c757a 100644
--- a/frontend/src/app/features/boards/board/board-actions/board-actions-registry.service.ts
+++ b/frontend/src/app/features/boards/board/board-actions/board-actions-registry.service.ts
@@ -30,7 +30,7 @@ export class BoardActionsRegistryService {
       icon: '',
       description: '',
       image: '',
-      disabled: this.bannersService.showBannerFor('board_view'),
+      disabled: !this.bannersService.allowsTo('board_view'),
     }));
   }
 
diff --git a/frontend/src/app/features/boards/board/board-partitioned-page/board-list-container.component.html b/frontend/src/app/features/boards/board/board-partitioned-page/board-list-container.component.html
index 7e2806ea85f..33429b92f95 100644
--- a/frontend/src/app/features/boards/board/board-partitioned-page/board-list-container.component.html
+++ b/frontend/src/app/features/boards/board/board-partitioned-page/board-list-container.component.html
@@ -1,6 +1,11 @@
 <ng-container *ngIf="(board$ | async) as board">
+  <op-enterprise-banner-frame
+    class="boards-list--enterprise-banner"
+    feature="board_view"
+    [dismissable]="true"
+  ></op-enterprise-banner-frame>
   <div
-    *ngIf="!needEnterpriseEdition; else enterpriseBanner"
+    *ngIf="available"
     class="boards-list--container"
     [ngClass]="{ '-free' : board.isFree }"
     #container
@@ -38,12 +43,4 @@
       </div>
     </div>
   </div>
-
-  <ng-template #enterpriseBanner>
-    <op-enterprise-banner-frame
-      class="boards-list--enterprise-banner"
-      feature="board_view"
-      [dismissable]="true"
-    ></op-enterprise-banner-frame>
-  </ng-template>
 </ng-container>
diff --git a/frontend/src/app/features/boards/board/board-partitioned-page/board-list-container.component.ts b/frontend/src/app/features/boards/board/board-partitioned-page/board-list-container.component.ts
index 94c382b289e..5f16eaf1125 100644
--- a/frontend/src/app/features/boards/board/board-partitioned-page/board-list-container.component.ts
+++ b/frontend/src/app/features/boards/board/board-partitioned-page/board-list-container.component.ts
@@ -88,7 +88,7 @@ export class BoardListContainerComponent extends UntilDestroyedMixin implements
 
   showHiddenListWarning:boolean = false;
 
-  needEnterpriseEdition = this.Banner.showBannerFor('board_view');
+  available = this.Banner.allowsTo('board_view');
 
   private currentQueryUpdatedMonitoring:Subscription;
 
@@ -126,7 +126,7 @@ readonly I18n:I18nService,
       );
 
     this.board$.subscribe((board) => {
-      this.needEnterpriseEdition = this.Banner.showBannerFor('board_view') && !board.isFree;
+      this.available = this.Banner.allowsTo('board_view') || board.isFree;
     });
 
     this.Boards.currentBoard$.next(id);
diff --git a/frontend/src/app/features/enterprise/enterprise-banner-frame.component.html b/frontend/src/app/features/enterprise/enterprise-banner-frame.component.html
index 7aa8d8d3aff..25e1af41340 100644
--- a/frontend/src/app/features/enterprise/enterprise-banner-frame.component.html
+++ b/frontend/src/app/features/enterprise/enterprise-banner-frame.component.html
@@ -1,5 +1,5 @@
 <turbo-frame
-  id="enterprise_banner_{{feature}}"
+  [id]="frameID"
   *ngIf="visible"
   [src]="frameURL"
 >
diff --git a/frontend/src/app/features/enterprise/enterprise-banner-frame.component.ts b/frontend/src/app/features/enterprise/enterprise-banner-frame.component.ts
index b3f9cb4b6d8..62aa7175b5c 100644
--- a/frontend/src/app/features/enterprise/enterprise-banner-frame.component.ts
+++ b/frontend/src/app/features/enterprise/enterprise-banner-frame.component.ts
@@ -43,6 +43,7 @@ export class EnterpriseBannerFrameComponent implements OnInit {
 
   visible:boolean;
   frameURL:string;
+  frameID:string;
 
   constructor(
     protected pathHelper:PathHelperService,
@@ -53,5 +54,8 @@ export class EnterpriseBannerFrameComponent implements OnInit {
   ngOnInit() {
     this.visible = this.banners.showBannerFor(this.feature);
     this.frameURL = this.pathHelper.bannerFramePath(this.feature, this.dismissable);
+
+    const trialSuffix = this.banners.trialling(this.feature) ? '_trial' : '';
+    this.frameID = `enterprise_banner_${this.feature}${trialSuffix}`;
   }
 }
diff --git a/frontend/src/app/features/invite-user-modal/project-selection/project-selection.component.ts b/frontend/src/app/features/invite-user-modal/project-selection/project-selection.component.ts
index 0c914b367ed..e6cbb6fc963 100644
--- a/frontend/src/app/features/invite-user-modal/project-selection/project-selection.component.ts
+++ b/frontend/src/app/features/invite-user-modal/project-selection/project-selection.component.ts
@@ -119,7 +119,14 @@ export class ProjectSelectionComponent implements OnInit {
   }
 
   private setPlaceholderOption():void {
-    if (this.bannersService.showBannerFor('placeholder_users')) {
+    if (this.bannersService.allowsTo('placeholder_users')) {
+      this.typeOptions.push({
+        value: PrincipalType.Placeholder,
+        title: this.I18n.t('js.invite_user_modal.type.placeholder.title'),
+        description: this.I18n.t('js.invite_user_modal.type.placeholder.description'),
+        disabled: false,
+      });
+    } else {
       this.typeOptions.push({
         value: PrincipalType.Placeholder,
         title: this.I18n.t('js.invite_user_modal.type.placeholder.title_no_ee'),
@@ -131,13 +138,6 @@ export class ProjectSelectionComponent implements OnInit {
         }),
         disabled: true,
       });
-    } else {
-      this.typeOptions.push({
-        value: PrincipalType.Placeholder,
-        title: this.I18n.t('js.invite_user_modal.type.placeholder.title'),
-        description: this.I18n.t('js.invite_user_modal.type.placeholder.description'),
-        disabled: false,
-      });
     }
   }
 
diff --git a/frontend/src/app/features/user-preferences/notifications-settings/page/notifications-settings-page.component.html b/frontend/src/app/features/user-preferences/notifications-settings/page/notifications-settings-page.component.html
index e5ea4522fbb..c25bab2e653 100644
--- a/frontend/src/app/features/user-preferences/notifications-settings/page/notifications-settings-page.component.html
+++ b/frontend/src/app/features/user-preferences/notifications-settings/page/notifications-settings-page.component.html
@@ -71,7 +71,7 @@
     <p>{{ text.dateAlerts.description }}</p>
   </div>
 
-  <div *ngIf="!eeShowBanners">
+  <div *ngIf="eeAvailable">
     <div
       class="op-reminder-settings-date-alerts--row"
       formGroupName="startDate"
diff --git a/frontend/src/app/features/user-preferences/notifications-settings/page/notifications-settings-page.component.ts b/frontend/src/app/features/user-preferences/notifications-settings/page/notifications-settings-page.component.ts
index 21d11713558..6333e0ebb95 100644
--- a/frontend/src/app/features/user-preferences/notifications-settings/page/notifications-settings-page.component.ts
+++ b/frontend/src/app/features/user-preferences/notifications-settings/page/notifications-settings-page.component.ts
@@ -54,7 +54,7 @@ export class NotificationsSettingsPageComponent extends UntilDestroyedMixin impl
 
   public availableTimesOverdue = overDueReminderTimes();
 
-  public eeShowBanners = false;
+  public eeAvailable = false;
 
   public form = new UntypedFormGroup({
     assignee: new UntypedFormControl(false),
@@ -137,7 +137,7 @@ export class NotificationsSettingsPageComponent extends UntilDestroyedMixin impl
 
   ngOnInit():void {
     this.form.disable();
-    this.eeShowBanners = this.bannersService.showBannerFor('date_alerts');
+    this.eeAvailable = this.bannersService.allowsTo('date_alerts');
 
     this
       .currentUserService
diff --git a/frontend/src/app/features/user-preferences/notifications-settings/table/notification-settings-table.component.html b/frontend/src/app/features/user-preferences/notifications-settings/table/notification-settings-table.component.html
index 739bdd7b0e3..826cf8ed54f 100644
--- a/frontend/src/app/features/user-preferences/notifications-settings/table/notification-settings-table.component.html
+++ b/frontend/src/app/features/user-preferences/notifications-settings/table/notification-settings-table.component.html
@@ -88,7 +88,7 @@
         </ng-container>
       </tr>
 
-      <tr *ngIf="!eeShowBanners">
+      <tr *ngIf="eeAvailable">
         <th class="op-table--cell op-table--cell_soft-heading">
           <h5>{{ text.dateAlerts.title }}</h5>
           <p>{{ text.dateAlerts.description }}</p>
@@ -98,7 +98,7 @@
         </ng-container>
       </tr>
 
-      <tr *ngIf="!eeShowBanners">
+      <tr *ngIf="eeAvailable">
         <th class="op-table--cell op-table--cell_soft-heading">
           {{ text.startDate }}
         </th>
@@ -122,7 +122,7 @@
         </ng-container>
       </tr>
 
-      <tr *ngIf="!eeShowBanners">
+      <tr *ngIf="eeAvailable">
         <th class="op-table--cell op-table--cell_soft-heading">
           {{ text.dueDate }}
         </th>
@@ -146,7 +146,7 @@
         </ng-container>
       </tr>
 
-      <tr *ngIf="!eeShowBanners">
+      <tr *ngIf="eeAvailable">
         <th class="op-table--cell op-table--cell_soft-heading">
           {{ text.overdue }}
         </th>
diff --git a/frontend/src/app/features/user-preferences/notifications-settings/table/notification-settings-table.component.ts b/frontend/src/app/features/user-preferences/notifications-settings/table/notification-settings-table.component.ts
index c00ba108824..70bb22ec674 100644
--- a/frontend/src/app/features/user-preferences/notifications-settings/table/notification-settings-table.component.ts
+++ b/frontend/src/app/features/user-preferences/notifications-settings/table/notification-settings-table.component.ts
@@ -21,7 +21,7 @@ export class NotificationSettingsTableComponent implements OnInit {
 
   @Input() settings:UntypedFormArray;
 
-  public eeShowBanners = false;
+  public eeAvailable = false;
 
   public availableTimes = [
     {
@@ -81,7 +81,7 @@ export class NotificationSettingsTableComponent implements OnInit {
   ) {}
 
   ngOnInit():void {
-    this.eeShowBanners = this.bannersService.showBannerFor('date_alerts');
+    this.eeAvailable = this.bannersService.allowsTo('date_alerts');
   }
 
   projectLink(href:string) {
diff --git a/frontend/src/app/features/work-packages/components/wp-baseline/baseline/baseline.component.ts b/frontend/src/app/features/work-packages/components/wp-baseline/baseline/baseline.component.ts
index 3ddfdcf5b9c..134974f85f9 100644
--- a/frontend/src/app/features/work-packages/components/wp-baseline/baseline/baseline.component.ts
+++ b/frontend/src/app/features/work-packages/components/wp-baseline/baseline/baseline.component.ts
@@ -98,7 +98,7 @@ export class OpBaselineComponent extends UntilDestroyedMixin implements OnInit {
 
   public tooltipPosition = SpotDropAlignmentOption.TopRight;
 
-  available = !this.Banner.showBannerFor('baseline_comparison');
+  available = this.Banner.allowsTo('baseline_comparison');
 
   public text = {
     toggle_title: this.I18n.t('js.baseline.toggle_title'),
diff --git a/frontend/src/app/features/work-packages/components/wp-buttons/wp-share-button/wp-share-button.component.ts b/frontend/src/app/features/work-packages/components/wp-buttons/wp-share-button/wp-share-button.component.ts
index 85d15a90be9..f739417f7b8 100644
--- a/frontend/src/app/features/work-packages/components/wp-buttons/wp-share-button/wp-share-button.component.ts
+++ b/frontend/src/app/features/work-packages/components/wp-buttons/wp-share-button/wp-share-button.component.ts
@@ -52,7 +52,7 @@ import { CollectionResource } from 'core-app/features/hal/resources/collection-r
 export class WorkPackageShareButtonComponent extends UntilDestroyedMixin implements OnInit {
   @Input() public workPackage:WorkPackageResource;
 
-  showEnterpriseIcon = this.bannersService.showBannerFor('work_package_sharing');
+  showEnterpriseIcon = !this.bannersService.allowsTo('work_package_sharing');
 
   shareCount$:Observable<number>;
 
diff --git a/frontend/src/app/features/work-packages/components/wp-custom-actions/wp-custom-actions.component.ts b/frontend/src/app/features/work-packages/components/wp-custom-actions/wp-custom-actions.component.ts
index 653735e4bb9..2d823d64f9c 100644
--- a/frontend/src/app/features/work-packages/components/wp-custom-actions/wp-custom-actions.component.ts
+++ b/frontend/src/app/features/work-packages/components/wp-custom-actions/wp-custom-actions.component.ts
@@ -48,7 +48,7 @@ export class WpCustomActionsComponent extends UntilDestroyedMixin implements OnI
 
   actions:CustomActionResource[] = [];
 
-  available = !this.bannersService.showBannerFor('custom_actions');
+  available = this.bannersService.allowsTo('custom_actions');
 
   constructor(
     readonly apiV3Service:ApiV3Service,
diff --git a/frontend/src/app/features/work-packages/components/wp-table/configuration-modal/tabs/highlighting-tab.component.html b/frontend/src/app/features/work-packages/components/wp-table/configuration-modal/tabs/highlighting-tab.component.html
index cd2a9fc3661..a98b2ee6331 100644
--- a/frontend/src/app/features/work-packages/components/wp-table/configuration-modal/tabs/highlighting-tab.component.html
+++ b/frontend/src/app/features/work-packages/components/wp-table/configuration-modal/tabs/highlighting-tab.component.html
@@ -9,7 +9,7 @@
     <div class="form--field">
       <label class="form--label">
         <input type="radio"
-               [attr.disabled]="disabledValue(eeShowBanners)"
+               [attr.disabled]="disabledValue(eeAvailable)"
                [(ngModel)]="highlightingMode"
                (change)="updateMode($event.target.value)"
                value="inline"
@@ -41,7 +41,7 @@
     <div class="form--field">
       <label class="form--label">
         <input type="radio"
-               [attr.disabled]="disabledValue(eeShowBanners)"
+               [attr.disabled]="disabledValue(eeAvailable)"
                [(ngModel)]="entireRowMode"
                (change)="updateMode('entire-row')"
                [value]="true"
@@ -54,7 +54,7 @@
           <ng-select #rowHighlightNgSelect
                      [items]="availableRowHighlightedAttributes"
                      [(ngModel)]="lastEntireRowAttribute"
-                     [disabled]="disabledValue(eeShowBanners)"
+                     [disabled]="disabledValue(eeAvailable)"
                      [clearable]="false"
                      (open)="onOpen(rowHighlightNgSelect)"
                      (change)="updateMode($event.value)"
@@ -72,7 +72,7 @@
     <div class="form--field">
       <label class="form--label">
         <input type="radio"
-               [attr.disabled]="disabledValue(eeShowBanners)"
+               [attr.disabled]="disabledValue(eeAvailable)"
                [(ngModel)]="highlightingMode"
                (change)="updateMode($event.target.value)"
                value="none"
diff --git a/frontend/src/app/features/work-packages/components/wp-table/configuration-modal/tabs/highlighting-tab.component.ts b/frontend/src/app/features/work-packages/components/wp-table/configuration-modal/tabs/highlighting-tab.component.ts
index e352e95cd69..38585a5cc62 100644
--- a/frontend/src/app/features/work-packages/components/wp-table/configuration-modal/tabs/highlighting-tab.component.ts
+++ b/frontend/src/app/features/work-packages/components/wp-table/configuration-modal/tabs/highlighting-tab.component.ts
@@ -28,7 +28,7 @@ export class WpTableConfigurationHighlightingTabComponent implements TabComponen
 
   public lastEntireRowAttribute:HighlightingMode = 'status';
 
-  public eeShowBanners = false;
+  public eeAvailable = false;
 
   public availableInlineHighlightedAttributes:HalResource[] = [];
 
@@ -74,10 +74,10 @@ export class WpTableConfigurationHighlightingTabComponent implements TabComponen
 
     this.setSelectedValues();
 
-    this.eeShowBanners = this.Banners.showBannerFor('conditional_highlighting');
+    this.eeAvailable = this.Banners.allowsTo('conditional_highlighting');
     this.updateMode(this.wpTableHighlight.current.mode);
 
-    if (this.eeShowBanners) {
+    if (!this.eeAvailable) {
       this.updateMode('none');
     }
   }
@@ -106,8 +106,8 @@ export class WpTableConfigurationHighlightingTabComponent implements TabComponen
     this.selectedAttributes = model;
   }
 
-  public disabledValue(value:boolean):string | null {
-    return value ? 'disabled' : null;
+  public disabledValue(allowed:boolean):string | null {
+    return allowed ? null : 'disabled';
   }
 
   public get availableHighlightedAttributes():HalResource[] {
diff --git a/frontend/src/app/features/work-packages/routing/wp-view-base/view-services/wp-view-highlighting.service.ts b/frontend/src/app/features/work-packages/routing/wp-view-base/view-services/wp-view-highlighting.service.ts
index f948d43ce32..858af243b1b 100644
--- a/frontend/src/app/features/work-packages/routing/wp-view-base/view-services/wp-view-highlighting.service.ts
+++ b/frontend/src/app/features/work-packages/routing/wp-view-base/view-services/wp-view-highlighting.service.ts
@@ -32,7 +32,7 @@ export class WorkPackageViewHighlightingService extends WorkPackageQueryStateSer
    */
   public shouldHighlightInline(name:string):boolean {
     // 1. Are we in inline mode or unable to render?
-    if (!this.isInline || this.Banners.showBannerFor('conditional_highlighting')) {
+    if (!this.isInline || !this.Banners.allowsTo('conditional_highlighting')) {
       return false;
     }
 
diff --git a/frontend/src/stimulus/controllers/dynamic/admin/custom-fields.controller.ts b/frontend/src/stimulus/controllers/dynamic/admin/custom-fields.controller.ts
index d0d72100077..06b8ac05944 100644
--- a/frontend/src/stimulus/controllers/dynamic/admin/custom-fields.controller.ts
+++ b/frontend/src/stimulus/controllers/dynamic/admin/custom-fields.controller.ts
@@ -55,11 +55,11 @@ export default class CustomFieldsController extends Controller {
 
   static values = {
     formatConfig: Array,
-    enterpriseEdition: Boolean,
+    hierarchyEnabled: Boolean,
   };
 
   declare readonly formatConfigValue:[string, string, string[]][];
-  declare readonly enterpriseEditionValue:boolean;
+  declare readonly hierarchyEnabledValue:boolean;
 
   declare readonly formatTarget:HTMLInputElement;
   declare readonly dragContainerTarget:HTMLElement;
@@ -252,14 +252,11 @@ export default class CustomFieldsController extends Controller {
 
   private toggleFormat(format:string) {
     if (this.hasSubmitButtonTarget) {
-      this.submitButtonTarget.disabled = format === 'hierarchy' && !this.enterpriseEditionValue;
+      this.submitButtonTarget.disabled = format === 'hierarchy' && !this.hierarchyEnabledValue;
     }
 
     this.formatConfigValue.forEach(([targetsName, operator, formats]) => {
-      let active = operator === 'only' ? formats.includes(format) : !formats.includes(format);
-      if (targetsName === 'enterpriseBanner' && this.enterpriseEditionValue) {
-        active = false;
-      }
+      const active = operator === 'only' ? formats.includes(format) : !formats.includes(format);
 
       const targets = this[`${targetsName}Targets` as keyof typeof this] as HTMLElement[];
       if (targets) {
diff --git a/lib/api/v3/configuration/configuration_representer.rb b/lib/api/v3/configuration/configuration_representer.rb
index e1a51d2f7d0..ce33491e3cc 100644
--- a/lib/api/v3/configuration/configuration_representer.rb
+++ b/lib/api/v3/configuration/configuration_representer.rb
@@ -100,7 +100,12 @@ module API
 
         property :available_features,
                  getter: ->(*) {
-                   EnterpriseToken.current&.available_features || []
+                   EnterpriseToken.available_features
+                 }
+
+        property :trialling_features,
+                 getter: ->(*) {
+                   EnterpriseToken.trialling_features
                  }
 
         property :allowed_link_protocols,
diff --git a/spec/components/enterprise_edition/banner_component_spec.rb b/spec/components/enterprise_edition/banner_component_spec.rb
index 0731ac03bb2..59b0eb34c75 100644
--- a/spec/components/enterprise_edition/banner_component_spec.rb
+++ b/spec/components/enterprise_edition/banner_component_spec.rb
@@ -144,7 +144,7 @@ RSpec.describe EnterpriseEdition::BannerComponent, type: :component do
   context "when banner is dismissed" do
     let(:preference) { build_stubbed(:user_preference) }
     let(:user) { build_stubbed(:user, preference:) }
-    let(:dismiss_key) { :some_enterprise_feature }
+    let(:dismiss_key) { "some_enterprise_feature" }
     let(:component_args) { { dismissable: true } }
 
     before do
@@ -164,7 +164,7 @@ RSpec.describe EnterpriseEdition::BannerComponent, type: :component do
     end
 
     context "when using a custom dismiss_key" do
-      let(:dismiss_key) { :foo }
+      let(:dismiss_key) { "foo" }
       let(:component_args) { { dismiss_key:, dismissable: true } }
 
       it_behaves_like "does not render the component"
@@ -295,4 +295,27 @@ RSpec.describe EnterpriseEdition::BannerComponent, type: :component do
       end
     end
   end
+
+  context "with a trial token" do
+    before do
+      allow(EnterpriseToken).to receive(:trialling?).and_return(true)
+    end
+
+    it_behaves_like "renders the component"
+
+    it "renders with trial overrides" do
+      render_component_in_mo
+
+      component = find_test_selector(component_test_selector)
+
+      expect(component[:class]).to include("op-enterprise-banner_trial")
+      expect(component[:class]).not_to include("op-enterprise-banner_medium")
+      expect(component[:class]).not_to include("op-enterprise-banner_large")
+
+      within(component) do
+        expect(page).to have_css(".op-enterprise-banner--close_icon")
+        expect(page).to have_content("Buy now")
+      end
+    end
+  end
 end
diff --git a/spec/features/custom_fields/custom_fields_spec.rb b/spec/features/custom_fields/custom_fields_spec.rb
index b33ce403253..14b99d7473d 100644
--- a/spec/features/custom_fields/custom_fields_spec.rb
+++ b/spec/features/custom_fields/custom_fields_spec.rb
@@ -80,6 +80,7 @@ RSpec.describe "custom fields", :js do
       label_possible_values = I18n.t("activerecord.attributes.custom_field.possible_values").upcase # Possible values, capitalized on UI
       label_default_value = I18n.t("activerecord.attributes.custom_field.default_value") # Default value
       label_is_required = I18n.t("activerecord.attributes.custom_field.is_required") # Required
+      label_ee_banner_hierarchy = I18n.t("ee.upsell.custom_field_hierarchies.description") # Hierarchy Enterprise banner
       # Spent time SFs don't show "Searchable". Not tested here.
       # Project CFs don't show "For all projects" and "Used as a filter". Not tested here.
       # Content right to left is not shown for Project CFs Long text. Strange. Not tested.
@@ -101,7 +102,7 @@ RSpec.describe "custom fields", :js do
         label_min_length, label_max_length, label_regexp, label_default_value, label_is_required
       )
       expect_page_not_to_have_texts(
-        label_multi_value, label_allow_non_open_versions, label_possible_values
+        label_multi_value, label_allow_non_open_versions, label_possible_values, label_ee_banner_hierarchy
       )
 
       select "Long text", from: "custom_field_field_format"
@@ -109,7 +110,7 @@ RSpec.describe "custom fields", :js do
         label_min_length, label_max_length, label_regexp, label_default_value, label_is_required
       )
       expect_page_not_to_have_texts(
-        label_multi_value, label_allow_non_open_versions, label_possible_values
+        label_multi_value, label_allow_non_open_versions, label_possible_values, label_ee_banner_hierarchy
       )
 
       # Both Integer and Float have min/max_len and regex as well which seems strange.
@@ -118,7 +119,7 @@ RSpec.describe "custom fields", :js do
         label_min_length, label_max_length, label_regexp, label_default_value, label_is_required
       )
       expect_page_not_to_have_texts(
-        label_multi_value, label_allow_non_open_versions, label_possible_values
+        label_multi_value, label_allow_non_open_versions, label_possible_values, label_ee_banner_hierarchy
       )
 
       select "Float", from: "custom_field_field_format"
@@ -126,7 +127,7 @@ RSpec.describe "custom fields", :js do
         label_min_length, label_max_length, label_regexp, label_default_value, label_is_required
       )
       expect_page_not_to_have_texts(
-        label_multi_value, label_allow_non_open_versions, label_possible_values
+        label_multi_value, label_allow_non_open_versions, label_possible_values, label_ee_banner_hierarchy
       )
 
       select "List", from: "custom_field_field_format"
@@ -134,14 +135,16 @@ RSpec.describe "custom fields", :js do
         label_multi_value, label_possible_values, label_is_required
       )
       expect_page_not_to_have_texts(
-        label_min_length, label_max_length, label_regexp, label_allow_non_open_versions, label_default_value
+        label_min_length, label_max_length, label_regexp, label_allow_non_open_versions,
+        label_default_value, label_ee_banner_hierarchy
       )
 
       select "Date", from: "custom_field_field_format"
       expect_page_to_have_texts(label_is_required)
       expect_page_not_to_have_texts(
         label_min_length, label_max_length, label_regexp, label_multi_value,
-        label_allow_non_open_versions, label_possible_values, label_default_value
+        label_allow_non_open_versions, label_possible_values, label_default_value,
+        label_ee_banner_hierarchy
       )
 
       select "Boolean", from: "custom_field_field_format"
@@ -150,7 +153,7 @@ RSpec.describe "custom fields", :js do
       )
       expect_page_not_to_have_texts(
         label_min_length, label_max_length, label_regexp, label_multi_value,
-        label_allow_non_open_versions, label_possible_values
+        label_allow_non_open_versions, label_possible_values, label_ee_banner_hierarchy
       )
 
       select "User", from: "custom_field_field_format"
@@ -159,7 +162,7 @@ RSpec.describe "custom fields", :js do
       )
       expect_page_not_to_have_texts(
         label_min_length, label_max_length, label_regexp, label_allow_non_open_versions,
-        label_possible_values, label_default_value
+        label_possible_values, label_default_value, label_ee_banner_hierarchy
       )
 
       select "Version", from: "custom_field_field_format"
@@ -168,8 +171,20 @@ RSpec.describe "custom fields", :js do
       )
       expect_page_not_to_have_texts(
         label_min_length, label_max_length, label_regexp,
-        label_possible_values, label_default_value
+        label_possible_values, label_default_value, label_ee_banner_hierarchy
       )
+
+      if hierarchy_type_available
+        select "Hierarchy", from: "custom_field_field_format"
+        expect_page_to_have_texts(
+          label_multi_value, label_is_required, label_ee_banner_hierarchy
+        )
+        expect_page_not_to_have_texts(
+          label_min_length, label_max_length, label_regexp, label_allow_non_open_versions,
+          label_possible_values, label_default_value
+        )
+        expect(page).to have_button("Save", disabled: true)
+      end
     end
 
     it "shows the correct breadcrumbs" do
@@ -186,14 +201,53 @@ RSpec.describe "custom fields", :js do
   end
 
   describe "work packages" do
+    let(:hierarchy_type_available) { true }
+
     it_behaves_like "creating a new custom field", "Work packages"
+
+    context "for hierarchy type" do
+      before do
+        cf_page.visit_tab "Work packages"
+
+        click_on "Create a new custom field"
+        wait_for_reload
+        cf_page.set_name "Ignored"
+
+        select "Hierarchy", from: "custom_field_field_format"
+      end
+
+      context "with an active enterprise token with custom_field_hierarchies feature", with_ee: [:custom_field_hierarchies] do
+        it "does not show the enterprise upsell banner and can save" do
+          expect(page).to have_no_text(I18n.t("ee.upsell.custom_field_hierarchies.description"))
+          expect(page).to have_button("Save", disabled: false)
+        end
+      end
+
+      context "with an active enterprise token without custom_field_hierarchies feature", with_ee: [:another_feature] do
+        it "shows the enterprise upsell banner and cannot save" do
+          expect(page).to have_text(I18n.t("ee.upsell.custom_field_hierarchies.description"))
+          expect(page).to have_button("Save", disabled: true)
+        end
+      end
+
+      context "with a trial enterprise token", :with_ee_trial, with_ee: [:custom_field_hierarchies] do
+        it "shows the enterprise upsell banner and can save" do
+          expect(page).to have_text(I18n.t("ee.upsell.custom_field_hierarchies.description"))
+          expect(page).to have_button("Save", disabled: false)
+        end
+      end
+    end
   end
 
   describe "time entries" do
+    let(:hierarchy_type_available) { false }
+
     it_behaves_like "creating a new custom field", "Spent time"
   end
 
   describe "versions" do
+    let(:hierarchy_type_available) { false }
+
     it_behaves_like "creating a new custom field", "Versions"
   end
 
@@ -255,7 +309,7 @@ RSpec.describe "custom fields", :js do
       check("custom_field_multi_value")
       check("custom_field_custom_options_attributes_0_default_value")
       check("custom_field_custom_options_attributes_2_default_value")
-      within all(".custom-option-row").first do
+      within first(".custom-option-row") do
         click_on "Move to bottom"
       end
       click_on "Save"
diff --git a/spec/features/custom_fields/hierarchy_custom_field_spec.rb b/spec/features/custom_fields/hierarchy_custom_field_spec.rb
index c8bcd094e20..1306c8ee206 100644
--- a/spec/features/custom_fields/hierarchy_custom_field_spec.rb
+++ b/spec/features/custom_fields/hierarchy_custom_field_spec.rb
@@ -37,7 +37,7 @@ RSpec.describe "custom fields of type hierarchy", :js do
   let(:hierarchy_page) { Pages::CustomFields::HierarchyPage.new }
 
   before do
-    allow(EnterpriseToken).to receive(:allows_to?).and_return(true)
+    allow(EnterpriseToken).to receive_messages(allows_to?: true, trialling?: false)
     login_as admin
   end
 
diff --git a/spec/support/shared/with_ee.rb b/spec/support/shared/with_ee.rb
index 4c4f900e454..4c2689238f0 100644
--- a/spec/support/shared/with_ee.rb
+++ b/spec/support/shared/with_ee.rb
@@ -47,7 +47,7 @@ end
 RSpec.configure do |config|
   config.before do |example|
     allowed = ee_actions(example)
-    if allowed.present?
+    if allowed.present? || example.metadata[:with_ee_trial]
       allowed = aggregate_parent_array(example, allowed.to_set)
 
       token_double = instance_double(EnterpriseToken)
@@ -65,6 +65,7 @@ RSpec.configure do |config|
         .to receive_messages(token_object: token_object_double,
                              available_features: allowed.to_a,
                              expired?: false,
+                             trial?: !!example.metadata[:with_ee_trial],
                              restrictions: {})
     end
   end