diff --git a/lib/ansible/runner/action_plugins/assert.py b/lib/ansible/runner/action_plugins/assert.py
index 8091326046..210dbc0af1 100644
--- a/lib/ansible/runner/action_plugins/assert.py
+++ b/lib/ansible/runner/action_plugins/assert.py
@@ -46,11 +46,12 @@ class ActionModule(object):
         if not 'that' in args:
             raise errors.AnsibleError('conditional required in "that" string')
 
-        result = utils.check_conditional(args['that'], self.runner.basedir, inject, fail_on_undefined=True)
+        if not isinstance(args['that'], list):
+            args['that'] = [ args['that'] ]
 
-        if not result:
-            result = dict(failed=True, assertion=args['that'], evaluated_to=result)
-        else:
-            result = dict(msg='ok', assertion=args['that'], evaluated_to=result)
+        for that in args['that']:
+            result = utils.check_conditional(args['that'], self.runner.basedir, inject, fail_on_undefined=True)
+            if not result:
+                return ReturnData(conn=conn, result=dict(failed=True, assertion=that, evaluated_to=result))
 
-        return ReturnData(conn=conn, result=result)
+        return ReturnData(conn=conn, result=dict(msg='all assertions passed'))
diff --git a/tests_new/integration/roles/test_copy/tasks/main.yml b/tests_new/integration/roles/test_copy/tasks/main.yml
index d3dbaeadb0..1a8192dec8 100644
--- a/tests_new/integration/roles/test_copy/tasks/main.yml
+++ b/tests_new/integration/roles/test_copy/tasks/main.yml
@@ -22,16 +22,19 @@
   copy: src=foo.txt dest={{output_file}}
   register: copy_result
 
-- assert: { that: "'changed' in copy_result" }
-- assert: { that: "'dest' in copy_result" }
-- assert: { that: "'group' in copy_result" }
-- assert: { that: "'gid' in copy_result" }
-- assert: { that: "'md5sum' in copy_result" }
-- assert: { that: "'owner' in copy_result" }
-- assert: { that: "'size' in copy_result" }
-- assert: { that: "'src' in copy_result" }
-- assert: { that: "'state' in copy_result" }
-- assert: { that: "'uid' in copy_result" }
+- name: assert basic copy worked
+  assert: 
+    that: 
+    - "'changed' in copy_result"
+    - "'dest' in copy_result"
+    - "'group' in copy_result"
+    - "'gid' in copy_result"
+    - "'md5sum' in copy_result"
+    - "'owner' in copy_result"
+    - "'size' in copy_result"
+    - "'src' in copy_result"
+    - "'state' in copy_result"
+    - "'uid' in copy_result"
 
 
 - name: verify that the file was marked as changed