diff --git a/src/ci_orchestrator/commands/template.py b/src/ci_orchestrator/commands/template.py
index f10c43d..d4741d2 100644
--- a/src/ci_orchestrator/commands/template.py
+++ b/src/ci_orchestrator/commands/template.py
@@ -668,18 +668,30 @@ def template_prepare_win(
     click.echo("[prepare-win] WinRM ready.")
 
     try:
-        # Switch the interactive shell to cmd.exe up front, before the toolchain
-        # runs, so every reboot in the Windows Update 3010 loop already boots
-        # without explorer — no shell crash-loop during heavy servicing. Drop the
-        # live explorer now too (Winlogon relaunches the shell = cmd). Re-affirmed
-        # before the final reboot and baked into post-install for redundancy.
-        click.echo("[prepare-win] Setting interactive shell to cmd.exe ...")
-        transport.run(
-            "Set-ItemProperty 'HKLM:\\SOFTWARE\\Microsoft\\Windows NT"
-            "\\CurrentVersion\\Winlogon' Shell 'cmd.exe' -Type String -Force\n"
-            "Stop-Process -Name explorer -Force -ErrorAction SilentlyContinue\n",
+        # Ensure the interactive shell is cmd.exe — via a clean reboot — before
+        # the toolchain runs, so explorer never runs during the heavy servicing
+        # (Windows Update 3010 loop) that would otherwise crash-loop it. Reboot
+        # only when the shell wasn't already cmd, so re-runs don't reboot need-
+        # lessly. Re-affirmed before the final reboot and baked into post-install.
+        shell_res = transport.run(
+            "(Get-ItemProperty 'HKLM:\\SOFTWARE\\Microsoft\\Windows NT"
+            "\\CurrentVersion\\Winlogon').Shell",
             check=False,
         )
+        if "cmd.exe" not in shell_res.stdout.strip().lower():
+            click.echo(
+                f"[prepare-win] Shell is '{shell_res.stdout.strip() or '?'}' — "
+                "setting cmd.exe and rebooting ..."
+            )
+            transport.run(
+                "Set-ItemProperty 'HKLM:\\SOFTWARE\\Microsoft\\Windows NT"
+                "\\CurrentVersion\\Winlogon' Shell 'cmd.exe' -Type String -Force",
+                check=False,
+            )
+            _reboot_and_wait(transport, guest_ip, 5986, winrm_timeout)
+            click.echo("[prepare-win] Shell is now cmd.exe.")
+        else:
+            click.echo("[prepare-win] Shell already cmd.exe — no reboot needed.")
 
         # Ensure C:\CI exists
         transport.run(
diff --git a/tests/python/test_commands_template.py b/tests/python/test_commands_template.py
index 8ed93e7..9e3a627 100644
--- a/tests/python/test_commands_template.py
+++ b/tests/python/test_commands_template.py
@@ -434,6 +434,8 @@ def _make_transport() -> MagicMock:
     def _run(script: str = "", **kwargs: object) -> WinRmResult:
         if "PercentProcessorTime" in script:  # pre-snapshot idle check
             return WinRmResult(stdout='{"cpu":2.0,"ram":21.0,"top":"idle"}', stderr="", returncode=0)
+        if ").Shell" in script:  # up-front shell check — already cmd, skip reboot
+            return WinRmResult(stdout="cmd.exe", stderr="", returncode=0)
         if "ConvertTo-Json" in script:
             return WinRmResult(stdout=val_json, stderr="", returncode=0)
         return WinRmResult(stdout="CI_EXITCODE:0", stderr="", returncode=0)