diff --git a/roles/add-build-sshkey/tasks/remote-windows.yaml b/roles/add-build-sshkey/tasks/remote-windows.yaml
index 9365c4364..abd0d3706 100644
--- a/roles/add-build-sshkey/tasks/remote-windows.yaml
+++ b/roles/add-build-sshkey/tasks/remote-windows.yaml
@@ -10,11 +10,16 @@
 
     # We use scp here as this is much more performant than ansible copy
     echo "Copy build ssh keys to node"
+    ssh -o BatchMode=yes -o ConnectTimeout=10 -o StrictHostKeyChecking=no {{ ansible_user }}@{{ ansible_host }} powershell "md -Force -Path .ssh"
     scp -B {{ zuul_temp_ssh_key }} {{ ansible_user }}@{{ ansible_host }}:.ssh/id_rsa
     scp -B {{ zuul_temp_ssh_key }}.pub {{ ansible_user }}@{{ ansible_host }}:.ssh/id_rsa.pub
 
     echo "Add build ssh keys to authorized_keys"
-    ssh -o BatchMode=yes {{ ansible_user }}@{{ ansible_host }} "type .ssh\\id_rsa.pub >> .ssh\\authorized_keys"
+    {% if win_admin_ssh | default(false) %}
+    ssh -o BatchMode=yes {{ ansible_user }}@{{ ansible_host }} cmd "type .ssh\\id_rsa.pub >> %programdata%\\ssh\\administrators_authorized_keys"
+    {% else %}
+    ssh -o BatchMode=yes {{ ansible_user }}@{{ ansible_host }} cmd "type .ssh\\id_rsa.pub >> .ssh\\authorized_keys"
+    {% endif %}
   register: windows_remote_ssh
   # Ignore errors here because this should not break non-ssh enabled windows hosts
   ignore_errors: true