diff --git a/test/integration/api_test/issues_test.rb b/test/integration/api_test/issues_test.rb
index 161beee..439e1d4 100644
--- a/test/integration/api_test/issues_test.rb
+++ b/test/integration/api_test/issues_test.rb
@@ -561,6 +561,63 @@ class Redmine::ApiTest::IssuesTest < Redmine::ApiTest::Base
     assert_response :success
   end
 
+  def test_create_issue_with_multiple_uploaded_files_as_xml
+    token1 = xml_upload('File content 1', credentials('jsmith'))
+    token2 = xml_upload('File content 2', credentials('jsmith'))
+
+    payload = <<-XML
+<?xml version="1.0" encoding="UTF-8" ?>
+<issue>
+  <project_id>1</project_id>
+  <tracker_id>1</tracker_id>
+  <subject>Issue with multiple attachments</subject>
+  <uploads type="array">
+    <upload>
+      <token>#{token1}</token>
+      <filename>test1.txt</filename>
+    </upload>
+    <upload>
+      <token>#{token2}</token>
+      <filename>test1.txt</filename>
+    </upload>
+  </uploads>
+</issue>
+XML
+
+    assert_difference 'Issue.count' do
+      post '/issues.xml', payload, {"CONTENT_TYPE" => 'application/xml'}.merge(credentials('jsmith'))
+      assert_response :created
+    end
+    issue = Issue.order('id DESC').first
+    assert_equal 2, issue.attachments.count
+  end
+
+  def test_create_issue_with_multiple_uploaded_files_as_json
+    token1 = json_upload('File content 1', credentials('jsmith'))
+    token2 = json_upload('File content 2', credentials('jsmith'))
+
+    payload = <<-JSON
+{
+  "issue": {
+    "project_id": "1",
+    "tracker_id": "1",
+    "subject": "Issue with multiple attachments",
+    "uploads": [
+      {"token": "#{token1}", "filename": "test1.txt"},
+      {"token": "#{token2}", "filename": "test2.txt"}
+    ]
+  }
+}
+JSON
+
+    assert_difference 'Issue.count' do
+      post '/issues.json', payload, {"CONTENT_TYPE" => 'application/json'}.merge(credentials('jsmith'))
+      assert_response :created
+    end
+    issue = Issue.order('id DESC').first
+    assert_equal 2, issue.attachments.count
+  end
+
   def test_update_issue_with_uploaded_file
     set_tmp_attachments_directory
     # upload the file
diff --git a/test/test_helper.rb b/test/test_helper.rb
index 44ea86f..22b96a8 100644
--- a/test/test_helper.rb
+++ b/test/test_helper.rb
@@ -271,6 +271,45 @@ module Redmine
       def teardown
         Setting.rest_api_enabled = '0'
       end
+
+      # Uploads content using the XML API and returns the attachment token
+      def xml_upload(content, credentials)
+        upload('xml', content, credentials)
+      end
+
+      # Uploads content using the JSON API and returns the attachment token
+      def json_upload(content, credentials)
+        upload('json', content, credentials)
+      end
+
+      def upload(format, content, credentials)
+        set_tmp_attachments_directory
+        assert_difference 'Attachment.count' do
+          post "/uploads.#{format}", content, {"CONTENT_TYPE" => 'application/octet-stream'}.merge(credentials)
+          assert_response :created
+        end
+        data = response_data
+        assert_kind_of Hash, data['upload']
+        token = data['upload']['token']
+        assert_not_nil token
+        token
+      end
+
+      # Parses the response body based on its content type
+      def response_data
+        unless response.content_type.to_s =~ /^application\/(.+)/
+          raise "Unexpected response type: #{response.content_type}"
+        end
+        format = $1
+        case format
+        when 'xml'
+          Hash.from_xml(response.body)
+        when 'json'
+          ActiveSupport::JSON.decode(response.body)
+        else
+          raise "Unknown response format: #{format}"
+        end
+      end
     end
 
     class Routing < Redmine::RoutingTest