diff --git a/changelogs/fragments/win_keep_remote_file_python26.yaml b/changelogs/fragments/win_keep_remote_file_python26.yaml
new file mode 100644
index 0000000000..20ca50112b
--- /dev/null
+++ b/changelogs/fragments/win_keep_remote_file_python26.yaml
@@ -0,0 +1,2 @@
+bugfixes:
+- powershell - Fix issue where setting ANSIBLE_KEEP_REMOTE_FILES fails when using Python 2.6 - https://github.com/ansible/ansible/issues/45490
diff --git a/lib/ansible/plugins/shell/powershell.py b/lib/ansible/plugins/shell/powershell.py
index ff62e3a227..784dd69cbd 100644
--- a/lib/ansible/plugins/shell/powershell.py
+++ b/lib/ansible/plugins/shell/powershell.py
@@ -57,7 +57,7 @@ import re
 import shlex
 
 from ansible.errors import AnsibleError
-from ansible.module_utils._text import to_text
+from ansible.module_utils._text import to_native, to_text
 from ansible.plugins.shell import ShellBase
 
 
@@ -1605,7 +1605,7 @@ class ShellModule(ShellBase):
 
         # non-pipelining
 
-        cmd_parts = shlex.split(cmd, posix=False)
+        cmd_parts = shlex.split(to_native(cmd), posix=False)
         cmd_parts = list(map(to_text, cmd_parts))
         if shebang and shebang.lower() == '#!powershell':
             if not self._unquote(cmd_parts[0]).lower().endswith('.ps1'):