diff --git a/test/integration/targets/win_psexec/aliases b/test/integration/targets/win_psexec/aliases
index a4da730eaa9..3cf5b97e805 100644
--- a/test/integration/targets/win_psexec/aliases
+++ b/test/integration/targets/win_psexec/aliases
@@ -1,2 +1 @@
 shippable/windows/group3
-unstable
diff --git a/test/integration/targets/win_psexec/tasks/main.yml b/test/integration/targets/win_psexec/tasks/main.yml
index a1245cdc316..a09401ccff7 100644
--- a/test/integration/targets/win_psexec/tasks/main.yml
+++ b/test/integration/targets/win_psexec/tasks/main.yml
@@ -41,12 +41,10 @@
     system: yes
     nobanner: true
   register: whoami_as_system
-
-- name: Test whoami as SYSTEM
-  assert:
-    that:
-    - whoami_as_system.rc == 0
-    - whoami_as_system.stdout == 'nt authority\system'
+  # Seems to be a bug with PsExec where the stdout can be empty, just retry the task to make this test a bit more stable
+  until: whoami_as_system.rc == 0 and whoami_as_system.stdout == 'nt authority\system'
+  retries: 3
+  delay: 2
 
 # FIXME: Behaviour is not consistent on all Windows systems
 #- name: Run whoami as ELEVATED