diff --git a/test/integration/roles/test_synchronize/files/bar.txt b/test/integration/roles/test_synchronize/files/bar.txt
new file mode 100644
index 0000000000..3e96db9b3e
--- /dev/null
+++ b/test/integration/roles/test_synchronize/files/bar.txt
@@ -0,0 +1 @@
+templated_var_loaded
diff --git a/test/integration/roles/test_synchronize/tasks/main.yml b/test/integration/roles/test_synchronize/tasks/main.yml
index 2afb68cd68..607191fb2c 100644
--- a/test/integration/roles/test_synchronize/tasks/main.yml
+++ b/test/integration/roles/test_synchronize/tasks/main.yml
@@ -20,21 +20,39 @@
 - name: cleanup old files
   shell: rm -rf {{output_dir}}/*
 
-- name: make a new file
-  copy: dest={{output_dir}}/foo.txt mode=0644 content="hello world"
+- name: create test new files
+  copy: dest={{output_dir}}/{{item}} mode=0644 content="hello world"
+  with_items:
+    - foo.txt
+    - bar.txt
 
 - name: synchronize file to new filename
   synchronize: src={{output_dir}}/foo.txt dest={{output_dir}}/foo.result
   register: sync_result
 
-- debug: var=sync_result
-
-- assert: 
-    that: 
+- assert:
+    that:
         - "'changed' in sync_result"
         - "sync_result.changed == true"
         - "'cmd' in sync_result"
         - "'rsync' in sync_result.cmd"
         - "'msg' in sync_result"
-        - "sync_result.msg == '>f+++++++++ foo.txt\n'"
+        - "sync_result.msg.startswith('>f+')"
+        - "sync_result.msg.endswith('+ foo.txt\n')"
 
+- name: synchronize files using with_items (issue#5965)
+  synchronize: src={{output_dir}}/{{item}} dest={{output_dir}}/{{item}}.result
+  with_items:
+    - foo.txt
+    - bar.txt
+  register: sync_result
+
+- debug: var=sync_result
+- assert:
+    that:
+        - "sync_result.changed"
+        - "sync_result.msg == 'All items completed'"
+        - "'results' in sync_result"
+        - "sync_result.results|length == 2"
+        - "sync_result.results[0].msg.endswith('+ foo.txt\n')"
+        - "sync_result.results[1].msg.endswith('+ bar.txt\n')"