diff --git a/modules/webhooks/app/workers/attachment_webhook_job.rb b/modules/webhooks/app/workers/attachment_webhook_job.rb
index 97a301136d6c..f05d2e855850 100644
--- a/modules/webhooks/app/workers/attachment_webhook_job.rb
+++ b/modules/webhooks/app/workers/attachment_webhook_job.rb
@@ -38,10 +38,7 @@ def accepted_in_project?
     webhook.enabled_for_project?(project.id)
   end
 
-  def payload_representer
-    User.system.run_given do |user|
-      ::API::V3::Attachments::AttachmentRepresenter
-        .create(resource, current_user: user, embed_links: true)
-    end
+  def payload_representer_class
+    ::API::V3::Attachments::AttachmentRepresenter
   end
 end
diff --git a/modules/webhooks/app/workers/project_webhook_job.rb b/modules/webhooks/app/workers/project_webhook_job.rb
index 732563074593..b96fd7771840 100644
--- a/modules/webhooks/app/workers/project_webhook_job.rb
+++ b/modules/webhooks/app/workers/project_webhook_job.rb
@@ -39,10 +39,7 @@ def accepted_in_project?
     end
   end
 
-  def payload_representer
-    User.system.run_given do |user|
-      ::API::V3::Projects::ProjectRepresenter
-        .create(resource, current_user: user, embed_links: true)
-    end
+  def payload_representer_class
+    ::API::V3::Projects::ProjectRepresenter
   end
 end
diff --git a/modules/webhooks/app/workers/represented_webhook_job.rb b/modules/webhooks/app/workers/represented_webhook_job.rb
index 0d4ca6a21163..0903395d604a 100644
--- a/modules/webhooks/app/workers/represented_webhook_job.rb
+++ b/modules/webhooks/app/workers/represented_webhook_job.rb
@@ -68,14 +68,22 @@ def payload_key
     raise NotImplementedError
   end
 
-  def payload_representer
+  def represented_payload
+    User.system.run_given do |user|
+      payload_representer_class
+        .create(resource, current_user: user, embed_links: true)
+        .to_hash # to_hash needs to be called within the system user block
+    end
+  end
+
+  def payload_representer_class
     raise NotImplementedError
   end
 
   def request_body
     {
       :action => event_name,
-      payload_key => payload_representer
+      payload_key => represented_payload
     }.to_json
   end
 end
diff --git a/modules/webhooks/app/workers/time_entry_webhook_job.rb b/modules/webhooks/app/workers/time_entry_webhook_job.rb
index c8c2013caddb..d9400d8da954 100644
--- a/modules/webhooks/app/workers/time_entry_webhook_job.rb
+++ b/modules/webhooks/app/workers/time_entry_webhook_job.rb
@@ -31,10 +31,7 @@ def payload_key
     :time_entry
   end
 
-  def payload_representer
-    User.system.run_given do |user|
-      ::API::V3::TimeEntries::TimeEntryRepresenter
-        .create(resource, current_user: user, embed_links: true)
-    end
+  def payload_representer_class
+    ::API::V3::TimeEntries::TimeEntryRepresenter
   end
 end
diff --git a/modules/webhooks/app/workers/work_package_webhook_job.rb b/modules/webhooks/app/workers/work_package_webhook_job.rb
index b25b01d043a1..4f9cb3928f1b 100644
--- a/modules/webhooks/app/workers/work_package_webhook_job.rb
+++ b/modules/webhooks/app/workers/work_package_webhook_job.rb
@@ -31,10 +31,7 @@ def payload_key
     :work_package
   end
 
-  def payload_representer
-    User.system.run_given do |user|
-      ::API::V3::WorkPackages::WorkPackageRepresenter
-        .create(resource, current_user: user, embed_links: true)
-    end
+  def payload_representer_class
+    ::API::V3::WorkPackages::WorkPackageRepresenter
   end
 end
diff --git a/modules/webhooks/spec/workers/project_webhook_job_spec.rb b/modules/webhooks/spec/workers/project_webhook_job_spec.rb
index 03f81354a124..3eac1560955a 100644
--- a/modules/webhooks/spec/workers/project_webhook_job_spec.rb
+++ b/modules/webhooks/spec/workers/project_webhook_job_spec.rb
@@ -29,7 +29,6 @@
 require "spec_helper"
 
 RSpec.describe ProjectWebhookJob, :webmock, type: :job do
-  shared_let(:user) { create(:admin) }
   shared_let(:request_url) { "http://example.net/test/42" }
   shared_let(:project) { create(:project, name: "Foo Bar") }
   shared_let(:webhook) { create(:webhook, all_projects: true, url: request_url, secret: nil) }
@@ -50,6 +49,10 @@
       { content_type: "text/plain", x_spec: "foobar" }
     end
 
+    let(:expected_payload) do
+      {}
+    end
+
     let(:stub) do
       stub_request(:post, stubbed_url.sub("http://", ""))
         .with(
@@ -57,7 +60,8 @@
             "action" => event,
             "project" => hash_including(
               "_type" => "Project",
-              "name" => "Foo Bar"
+              "name" => "Foo Bar",
+              **expected_payload
             )
           ),
           headers: request_headers
@@ -78,7 +82,6 @@
 
     before do
       allow(Webhooks::Webhook).to receive(:find).with(webhook.id).and_return(webhook)
-      login_as user
       stub
     end
 
@@ -133,7 +136,7 @@
     end
   end
 
-  describe "triggering a projec creation" do
+  describe "triggering a project creation" do
     it_behaves_like "a project webhook call" do
       let(:event) { "project:created" }
     end
@@ -146,4 +149,30 @@
       let(:response_body) { "not found" }
     end
   end
+
+  describe "triggering an update with a custom field set" do
+    shared_let(:custom_field) { create(:project_custom_field, :string, projects: [project]) }
+    shared_let(:custom_value) do
+      create(:custom_value,
+             custom_field:,
+             customized: project,
+             value: "wat")
+    end
+
+    it_behaves_like "a project webhook call" do
+      let(:expected_payload) do
+        { custom_field.attribute_name(:camel_case) => "wat" }
+      end
+
+      it "includes the custom field value" do
+        subject
+
+        expect(stub).to have_been_requested
+
+        log = Webhooks::Log.last
+        request = JSON.parse(log.request_body)
+        expect(request["project"][custom_field.attribute_name(:camel_case)]).to eq "wat"
+      end
+    end
+  end
 end