diff --git a/scripts/iiab-update b/scripts/iiab-update
index 4e2fe7aff..63f4a8a68 100755
--- a/scripts/iiab-update
+++ b/scripts/iiab-update
@@ -38,9 +38,14 @@
     fi
     echo -e "\n\n\e[4mNow running: git pull https://github.com/iiab/iiab --no-rebase --no-edit\e[0m\n"
     git pull https://github.com/iiab/iiab --no-rebase --no-edit
+    echo
+    if grep -q 'tailscale_installed: True' /etc/iiab/iiab_state.yml; then
+        echo -e "\e[4mNow running: cp -u roles/tailscale/templates/iiab-vpn /usr/bin\e[0m\n"
+        cp -u roles/tailscale/templates/iiab-vpn /usr/bin
+    fi
     if [[ $1 == "-f" || $1 == "--fast" ]]; then    # Otherwise ./runrole does it below! (as Ansible runs roles/0-init)
         cd scripts
-        echo -e "\n\e[4mNow running: cp -u iiab-update iiab-summary iiab-diagnostics iiab-root-login /usr/bin\e[0m\n"
+        echo -e "\e[4mNow running: cp -u iiab-update iiab-summary iiab-diagnostics iiab-root-login /usr/bin\e[0m\n"
         cp -u iiab-update iiab-summary iiab-diagnostics iiab-root-login /usr/bin
     fi