diff --git a/app/models/project_services/jira_service.rb b/app/models/project_services/jira_service.rb
index 1c065e1ddbdb118d3b2c6f7f5c4d0fca17ee8078..2be35b6ea9dc18633ddd65c6ab124cfc18f2c768 100644
--- a/app/models/project_services/jira_service.rb
+++ b/app/models/project_services/jira_service.rb
@@ -46,6 +46,8 @@ class JiraService < IssueTrackerService
       context_path: url.path,
       auth_type: :basic,
       read_timeout: 120,
+      use_cookies: true,
+      additional_cookies: ['OBBasicAuth=fromDialog'],
       use_ssl: url.scheme == 'https'
     }
   end
diff --git a/changelogs/unreleased/feature-40842-provide-oracles-webgate-cookies-to-jira-requests.yml b/changelogs/unreleased/feature-40842-provide-oracles-webgate-cookies-to-jira-requests.yml
new file mode 100644
index 0000000000000000000000000000000000000000..d5ff5bc462796a725e167ccb976a9aca58aade49
--- /dev/null
+++ b/changelogs/unreleased/feature-40842-provide-oracles-webgate-cookies-to-jira-requests.yml
@@ -0,0 +1,6 @@
+---
+title: Provide additional cookies to JIRA service requests to allow Oracle WebGates
+  Basic Auth
+merge_request:
+author: Stanislaw Wozniak
+type: changed
diff --git a/doc/user/project/integrations/jira.md b/doc/user/project/integrations/jira.md
index 93aec56f8dcd9046e0b14abe28275359e828eaa0..7dc234a9759f1303f18dc9e74a834ca5f3a888fc 100644
--- a/doc/user/project/integrations/jira.md
+++ b/doc/user/project/integrations/jira.md
@@ -98,6 +98,9 @@ password as they will be needed when configuring GitLab in the next section.
 - GitLab 8.14 introduced a new way to integrate with JIRA which greatly simplified
   the configuration options you have to enter. If you are using an older version,
   [follow this documentation][jira-repo-old-docs].
+- In order to support Oracle's Access Manager, GitLab will send additional cookies
+  to enable Basic Auth. The cookie being added to each request is `OBBasicAuth` with
+  a value of `fromDialog`.
 
 To enable JIRA integration in a project, navigate to the
 [Integrations page](project_services.md#accessing-the-project-services), click
diff --git a/spec/models/project_services/jira_service_spec.rb b/spec/models/project_services/jira_service_spec.rb
index ad22fb2a386e82be1f3ed5609c3a95daf64cde7e..c9b3c6cf602dedc7a4df6b066463f626b69d690d 100644
--- a/spec/models/project_services/jira_service_spec.rb
+++ b/spec/models/project_services/jira_service_spec.rb
@@ -395,6 +395,26 @@ describe JiraService do
     end
   end
 
+  describe 'additional cookies' do
+    let(:project) { create(:project) }
+
+    context 'provides additional cookies to allow basic auth with oracle webgate' do
+      before do
+        @service = project.create_jira_service(
+          active: true, properties: { url: 'http://jira.com' })
+      end
+
+      after do
+        @service.destroy!
+      end
+
+      it 'is initialized' do
+        expect(@service.options[:use_cookies]).to eq(true)
+        expect(@service.options[:additional_cookies]).to eq(["OBBasicAuth=fromDialog"])
+      end
+    end
+  end
+
   describe 'project and issue urls' do
     let(:project) { create(:project) }