diff --git a/src/ci_orchestrator/commands/template.py b/src/ci_orchestrator/commands/template.py
index 3bc15d4..59c35ae 100644
--- a/src/ci_orchestrator/commands/template.py
+++ b/src/ci_orchestrator/commands/template.py
@@ -432,10 +432,26 @@ def template_prepare_win(
     if not build_password:
         build_password = click.prompt(f"New {build_username} password", hide_input=True)
 
-    # --- Backend: start VM and detect IP ---
+    # --- Pre-flight snapshot conflict check (terminal still clean here) ---
+    # Must happen before any WinRM/pypsrp calls, which alter tty state and
+    # prevent readline() from receiving \n on Enter.
     config = load_config()
     backend = WorkstationVmrunBackend(vmrun_path=config.vmrun_path)
     handle = VmHandle(identifier=str(vmx_path), name=vmx_path.stem)
+    existing_snapshots = backend.list_snapshots(handle)
+    do_recreate_snapshot = True
+    if snapshot in existing_snapshots:
+        click.echo(f"[prepare-win] Snapshot '{snapshot}' already exists.")
+        if recreate_snapshot:
+            click.echo(f"[prepare-win] --recreate-snapshot set: will delete and recreate.")
+        else:
+            sys.stdout.write(f"[prepare-win] Delete and recreate '{snapshot}'? [y/N] ")
+            sys.stdout.flush()
+            raw = sys.stdin.readline()
+            do_recreate_snapshot = raw.strip().lower() in ("y", "yes")
+        if not do_recreate_snapshot:
+            click.echo("[prepare-win] Keeping existing snapshot. Provisioning aborted.")
+            return
 
     if not backend.is_running(handle):
         click.echo(f"[prepare-win] Starting VM: {vmx_path.name} ...")
@@ -664,22 +680,10 @@ Register-ScheduledTask -TaskName 'CI-StaticIp' `
         raise click.ClickException("VM did not power off within 120s.")
     click.echo("[prepare-win] VM powered off.")
 
-    # Create snapshot
+    # Create snapshot — conflict already resolved at pre-flight above.
     vmrun_exe = backend.vmrun_path
-    existing = backend.list_snapshots(handle)
-    if snapshot in existing:
-        click.echo(f"[prepare-win] Snapshot '{snapshot}' already exists.")
-        if recreate_snapshot:
-            do_recreate = True
-        else:
-            sys.stdout.write(f"[prepare-win] Delete and recreate '{snapshot}'? [y/N] ")
-            sys.stdout.flush()
-            raw = sys.stdin.readline()
-            do_recreate = raw.strip().lower() in ("y", "yes")
-        if not do_recreate:
-            click.echo("[prepare-win] Keeping existing snapshot. Provisioning complete.")
-            return
-        click.echo(f"[prepare-win] Deleting snapshot '{snapshot}' ...")
+    if snapshot in backend.list_snapshots(handle):
+        click.echo(f"[prepare-win] Deleting existing snapshot '{snapshot}' ...")
         subprocess.run(
             [vmrun_exe, "-T", "ws", "deleteSnapshot", str(vmx_path), snapshot],
             check=True,