diff --git a/changelogs/fragments/11838-homebrew-cask-upgrade-latest.yml b/changelogs/fragments/11838-homebrew-cask-upgrade-latest.yml
new file mode 100644
index 0000000000..ecaa3af02c
--- /dev/null
+++ b/changelogs/fragments/11838-homebrew-cask-upgrade-latest.yml
@@ -0,0 +1,6 @@
+bugfixes:
+  - homebrew_cask - fix false task failure when upgrading casks with ``version=latest``;
+    the post-upgrade check incorrectly re-ran ``brew outdated`` (which always lists ``latest``
+    casks as outdated under ``--greedy``), now uses the command exit code instead
+    (https://github.com/ansible-collections/community.general/issues/1647,
+    https://github.com/ansible-collections/community.general/pull/11838).
diff --git a/plugins/modules/homebrew_cask.py b/plugins/modules/homebrew_cask.py
index 316f3aef85..9677bc65fc 100644
--- a/plugins/modules/homebrew_cask.py
+++ b/plugins/modules/homebrew_cask.py
@@ -656,7 +656,7 @@ class HomebrewCask:
         else:
             rc, out, err = self.module.run_command(cmd)
 
-        if self._current_cask_is_installed() and not self._current_cask_is_outdated():
+        if rc == 0:
             self.changed_count += 1
             self.changed = True
             self.message = f"Cask upgraded: {self.current_cask}"