diff --git a/tests/fixtures/workspacebuilder/window_automatic_rename.yaml b/tests/fixtures/workspacebuilder/window_automatic_rename.yaml
index 08329afcfea..a3640f4dedc 100644
--- a/tests/fixtures/workspacebuilder/window_automatic_rename.yaml
+++ b/tests/fixtures/workspacebuilder/window_automatic_rename.yaml
@@ -6,7 +6,7 @@ windows:
     automatic-rename: on
   panes:
   - shell_command:
-    - cmd: sh
+    - cmd: man ls
     start_directory: '~'
   - shell_command:
     - cmd: echo "hey"
diff --git a/tests/test_workspacebuilder.py b/tests/test_workspacebuilder.py
index 2ab04a9363f..b347fb36723 100644
--- a/tests/test_workspacebuilder.py
+++ b/tests/test_workspacebuilder.py
@@ -11,7 +11,7 @@
 import libtmux
 from libtmux import Window
 from libtmux.common import has_gte_version
-from libtmux.test import retry, temp_session
+from libtmux.test import retry, retry_until, temp_session
 from tmuxp import config, exc
 from tmuxp.cli.load import load_plugins
 from tmuxp.workspacebuilder import WorkspaceBuilder
@@ -359,6 +359,12 @@ def test_automatic_rename_option(session):
     sconfig = kaptan.Kaptan(handler="yaml")
     sconfig = sconfig.import_config(yaml_config).get()
 
+    # This should be a command guaranteed to be terminal name across systems
+    portable_command = sconfig["windows"][0]["panes"][0]["shell_command"][0]["cmd"]
+    # If a command is like "man ls", get the command base name, "ls"
+    if " " in portable_command:
+        portable_command = portable_command.split(" ")[0]
+
     builder = WorkspaceBuilder(sconf=sconfig)
 
     window_count = len(session._windows)  # current window count
@@ -380,31 +386,24 @@ def test_automatic_rename_option(session):
     assert s.name != "tmuxp"
     w = s.windows[0]
 
-    while retry():
+    def check_window_name_mismatch() -> bool:
         session.server._update_windows()
-        if w.name != "sh":
-            break
+        return w.name != portable_command
 
-    assert w.name != "sh"
+    assert retry_until(check_window_name_mismatch, 2, interval=0.25)
 
     pane_base_index = w.show_window_option("pane-base-index", g=True)
     w.select_pane(pane_base_index)
 
-    while retry():
+    def check_window_name_match() -> bool:
         session.server._update_windows()
-        if w.name == "sh":
-            break
+        return w.name == portable_command
 
-    assert w.name == "sh"
+    assert retry_until(check_window_name_match, 2, interval=0.25)
 
     w.select_pane("-D")
 
-    while retry():
-        session.server._update_windows()
-        if w["window_name"] != "sh":
-            break
-
-    assert w.name != "sh"
+    assert retry_until(check_window_name_mismatch, 2, interval=0.25)
 
 
 def test_blank_pane_count(session):