diff --git a/app/assets/javascripts/admin/addon/components/webhook-events.hbs b/app/assets/javascripts/admin/addon/components/webhook-events.hbs
index 7bfdeb1111d..0ba3222c84e 100644
--- a/app/assets/javascripts/admin/addon/components/webhook-events.hbs
+++ b/app/assets/javascripts/admin/addon/components/webhook-events.hbs
@@ -13,6 +13,12 @@
       class="delivery-status-filters"
     />
 
+    <DButton
+      @icon="sync"
+      @label="admin.web_hooks.events.redeliver_failed"
+      @action={{this.redeliverFailed}}
+    />
+
     <DButton
       @icon="paper-plane"
       @label="admin.web_hooks.events.ping"
diff --git a/app/assets/javascripts/admin/addon/components/webhook-events.js b/app/assets/javascripts/admin/addon/components/webhook-events.js
index fede8d838a7..63a031014d1 100644
--- a/app/assets/javascripts/admin/addon/components/webhook-events.js
+++ b/app/assets/javascripts/admin/addon/components/webhook-events.js
@@ -11,10 +11,16 @@ import I18n from "discourse-i18n";
 export default class WebhookEvents extends Component {
   @service messageBus;
   @service store;
+  @service dialog;
 
   @tracked pingEnabled = true;
   @tracked events = [];
   @tracked incomingEventIds = [];
+  @tracked loading = false;
+  @tracked showProgress = false;
+  @tracked processedTopicCount = 0;
+  @tracked count = 0;
+  @tracked eventIds = [];
 
   @readOnly("incomingEventIds.length") incomingCount;
   @gt("incomingCount", 0) hasIncoming;
@@ -117,4 +123,27 @@ export default class WebhookEvents extends Component {
       popupAjaxError(error);
     }
   }
+
+  @action
+  redeliverFailed() {
+    this.eventIds = this.events.content.map((event) => event.id);
+
+    this.count = this.events.length;
+    return this.dialog.yesNoConfirm({
+      message: I18n.t("admin.web_hooks.events.bulk_redeliver_confirm", {
+        count: this.count,
+      }),
+      didConfirm: async () => {
+        try {
+          const json = await ajax(
+            `/admin/api/web_hooks/${this.args.webhookId}/events/bulk_redeliver`,
+            { type: "POST", data: { event_ids: this.eventIds } }
+          );
+          this.args.event.setProperties(json.web_hook_event);
+        } catch (e) {
+          popupAjaxError(e);
+        }
+      },
+    });
+  }
 }
diff --git a/app/controllers/admin/web_hooks_controller.rb b/app/controllers/admin/web_hooks_controller.rb
index 8c99e6a7702..64945205f92 100644
--- a/app/controllers/admin/web_hooks_controller.rb
+++ b/app/controllers/admin/web_hooks_controller.rb
@@ -135,6 +135,13 @@ class Admin::WebHooksController < Admin::AdminController
     end
   end
 
+  def bulk_redeliver_events
+    limit = 50
+    offset = params[:offset].to_i
+    failed_events = @web_hook.web_hook_events.failed.limit(limit).offset(offset)
+    render_serialized(failed_events, AdminWebHookEventSerializer, root: "web_hook_event")
+  end
+
   def ping
     Jobs.enqueue(
       :emit_web_hook_event,
diff --git a/config/locales/client.en.yml b/config/locales/client.en.yml
index caa093d2a41..adfb2a952b0 100644
--- a/config/locales/client.en.yml
+++ b/config/locales/client.en.yml
@@ -5347,6 +5347,7 @@ en:
           request: "Request"
           response: "Response"
           redeliver_confirm: "Are you sure you want to redeliver the same payload?"
+          bulk_redeliver_confirm: "Are you sure you want to redeliver %{count} webhook events? (You can redeliver up to 50 failed events at once.)"
           headers: "Headers"
           payload: "Payload"
           body: "Body"
@@ -5356,6 +5357,7 @@ en:
           timestamp: "Created"
           completion: "Completion Time"
           actions: "Actions"
+          redeliver_failed: "Redeliver Failed"
           filter_status:
             all: "All Events"
             successful: "Delivered"
diff --git a/config/routes.rb b/config/routes.rb
index 6058895335b..626ac09d8d3 100644
--- a/config/routes.rb
+++ b/config/routes.rb
@@ -344,6 +344,7 @@ Discourse::Application.routes.draw do
           get "web_hook_events/:id" => "web_hooks#list_events", :as => :web_hook_events
           get "web_hooks/:id/events/bulk" => "web_hooks#bulk_events"
           post "web_hooks/:web_hook_id/events/:event_id/redeliver" => "web_hooks#redeliver_event"
+          post "web_hooks/:web_hook_id/events/bulk_redeliver" => "web_hooks#bulk_redeliver_events"
           post "web_hooks/:id/ping" => "web_hooks#ping"
         end
       end