diff --git a/ansible/playbooks/win_update.yml b/ansible/playbooks/win_update.yml
index ae4cec9..04c2ae9 100644
--- a/ansible/playbooks/win_update.yml
+++ b/ansible/playbooks/win_update.yml
@@ -1,6 +1,6 @@
 ---
-- hosts: "{{ target_host }}"
-  gather_facts: true
+- hosts: "meta-os_windows"
+  gather_facts: false
   vars_files:
     - ../vars/common.yml 
     - ../vars/connection.yml
diff --git a/ansible/roles/win_update/tasks/update.yml b/ansible/roles/win_update/tasks/update.yml
index 0a502a6..bfeda45 100644
--- a/ansible/roles/win_update/tasks/update.yml
+++ b/ansible/roles/win_update/tasks/update.yml
@@ -1,30 +1,65 @@
 ---
-- name: Update VM
-  tags: update_vm
+- name: Install client VM updates and reboot as much as needed
   block:
-    - name: Clear update cache
-      win_shell: |
-        UsoClient RefreshSettings
-        UsoClient ScanInstallWait
-
-    - name: Update Windows
+    - name: Install Windows updates (looped)
+      tags: update_windows
       ansible.windows.win_updates:
-        category_names: '*'
-        skip_optional: true
+        category_names:
+          - CriticalUpdates
+          - DefinitionUpdates
+          - SecurityUpdates
+          - UpdateRollups
         reboot: true
-        reboot_timeout: 3600
-      ignore_errors: true
+      register: update_result
+      retries: 5
+      delay: 30
+      until: update_result.reboot_required == false
 
-    - name: Update Windows (again)
+    - name: Wait for host to come back online
+      tags: update_windows
+      ansible.builtin.wait_for_connection:
+        timeout: 600
+
+    - name: Update all choco packages
+      win_command: choco upgrade all -y
+      tags: update_choco
+
+    - name: Update Start Menu Shortcuts in XML on remote Windows machines
+      tags: update_start_menu
+      block:
+        - name: Copy Python script to target machine
+          ansible.windows.win_template:
+            src: "{{ script_name }}"
+            dest: "{{ script_path }}"
+            force: true
+
+        - name: Copy current XML to backup location
+          win_copy:
+            remote_src: true
+            src: "{{ start_menu_xml }}"
+            dest: "{{ backup_xml }}"
+
+        - name: Run Python script on remote machine
+          win_command: python "{{ script_path }}.xml"
+  when: "inventory_hostname in groups['meta-type_client']|default([])"
+
+- name: Install Server VM updates and reboot as much as needed
+  tags: update_windows
+  block:
+    - name: Install Windows updates (looped)
       ansible.windows.win_updates:
-        category_names: '*'
+        category_names:
+          - CriticalUpdates
+          - DefinitionUpdates
+          - SecurityUpdates
+          - UpdateRollups
         reboot: true
-        reboot_timeout: 3600
-      ignore_errors: true
+      register: update_result
+      retries: 5
+      delay: 30
+      until: update_result.reboot_required == false
 
-    - name: Logging action
-      vars:
-        ansible_connection: local
-      ansible.builtin.shell:
-        cmd:  echo "Update {{ os_project }}-{{ ansible_hostname }} $(date '+%Y-%m-%d %H:%M:%S')" >> /deployments/{{ os_project }}-{{ win_project }}/action.log
-      delegate_to: localhost
+    - name: Wait for host to come back online
+      ansible.builtin.wait_for_connection:
+        timeout: 600
+  when: "inventory_hostname in groups['meta-type_server']"
diff --git a/ansible/roles/win_update/templates/newXML.py b/ansible/roles/win_update/templates/newXML.py
new file mode 100644
index 0000000..3140631
--- /dev/null
+++ b/ansible/roles/win_update/templates/newXML.py
@@ -0,0 +1,146 @@
+import os
+import shutil
+import re
+import xml.etree.ElementTree as ET
+
+original_xml = "{{ start_menu_xml }}"
+backup_xml = "{{ backup_xml }}"
+
+# This script assumes backup and copying already handled by Ansible
+
+START_MENU_PATHS = {
+    "%ALLUSERSPROFILE%\\Microsoft\\Windows\\Start Menu\\Programs": os.path.expandvars(r"%ALLUSERSPROFILE%\Microsoft\Windows\Start Menu\Programs")
+}
+
+def extract_version(filename):
+    match = re.search(r'(\d+\.\d+\.\d+|\d+)', filename)
+    if match:
+        return tuple(map(int, match.group(0).split('.')))
+    return (0,)
+
+def adjust_app_name(app_name):
+    return f"{app_name} " if len(app_name) == 1 else app_name
+
+def remove_bracketed_text(filename):
+    return re.sub(r"[\(\[].*?[\)\]]", "", filename).strip()
+
+def folder_has_standalone_version(folder_name):
+    return bool(re.search(r'\b\d+(?:\.\d+){1,3}\b', folder_name))
+
+def clean_folder_name(folder_name):
+    return re.sub(r'\b\d+(?:\.\d+){1,3}\b', '', folder_name).strip()
+
+def remove_version_number(app_name):
+    if re.search(r'\d+\.\d+(\.\d+)*$', app_name):
+        return re.sub(r'(\s*\d+\.\d+(\.\d+)*\s*)$', '', app_name).strip()
+    return app_name
+
+def is_extra_word_present(filename, base_name):
+    name_without_ext = os.path.splitext(filename)[0].lower()
+    return name_without_ext != base_name.lower()
+
+def version_sort_key(filename, base_name):
+    version = extract_version(filename)
+    cleaned_name = remove_bracketed_text(filename)
+    padded_version = version + (0,) * (3 - len(version))
+    return (
+        is_extra_word_present(filename, base_name),
+        len(cleaned_name),
+        -padded_version[0],
+        -padded_version[1] if len(padded_version) > 1 else 0,
+        -padded_version[2] if len(padded_version) > 2 else 0
+    )
+
+def get_clean_base_name(app_name):
+    return re.sub(r"(\s*\d+(\.\d+)*\s*)+$", "", app_name).strip()
+
+def find_best_match(app_name, available_files):
+    base_name = get_clean_base_name(app_name)
+    adjusted_name = adjust_app_name(base_name)
+    start_matches = [file for file in available_files if file.lower().startswith(adjusted_name.lower())]
+    exact_match = [f for f in start_matches if os.path.splitext(f)[0].lower() == adjusted_name.lower()]
+    if exact_match:
+        print(f"Exact match for {app_name}: {exact_match[0]}")
+        return exact_match[0]
+    best = min(start_matches, key=lambda f: version_sort_key(f, adjusted_name)) if start_matches else None
+    print(f"Best match for {app_name}: {best}")
+    return best
+
+def convert_to_env_path(abs_path):
+    for env_path, abs_root in START_MENU_PATHS.items():
+        if abs_path.startswith(abs_root):
+            return abs_path.replace(abs_root, env_path)
+    return abs_path
+
+def find_shortcut_paths(app_names):
+    app_paths = {}
+    all_lnk_files = {}
+
+    for _, start_menu in START_MENU_PATHS.items():
+        for root, _, files in os.walk(start_menu):
+            for file in files:
+                if file.endswith(".lnk"):
+                    full_path = os.path.join(root, file)
+                    all_lnk_files[file] = full_path
+
+    for app_name in app_names:
+        best_match = find_best_match(app_name, all_lnk_files.keys())
+        if best_match:
+            env_path = convert_to_env_path(all_lnk_files[best_match])
+            app_paths[app_name] = env_path
+            print(f"Mapped {app_name} to {env_path}")
+        else:
+            print(f"No match found for {app_name}")
+
+    return app_paths
+
+def extract_app_names_and_paths(xml_file):
+    tree = ET.parse(xml_file)
+    root = tree.getroot()
+    apps = {}
+
+    for tile in root.findall(".//{*}DesktopApplicationTile"):
+        link_path = tile.get("DesktopApplicationLinkPath")
+        if link_path:
+            folder_name = os.path.basename(os.path.dirname(link_path))
+            lnk_name = os.path.splitext(os.path.basename(link_path))[0]
+
+            if folder_has_standalone_version(folder_name):
+                app_name = clean_folder_name(folder_name)
+            else:
+                app_name = remove_bracketed_text(lnk_name)
+
+            app_name = remove_version_number(app_name)
+            app_name = adjust_app_name(app_name)
+            apps[app_name] = link_path
+            print(f"Extracted {app_name} from {link_path}")
+
+    return apps
+
+def update_xml_paths(xml_file, old_new_paths):
+    with open(xml_file, "r", encoding="utf-8") as file:
+        content = file.read()
+
+    for old_path, new_path in old_new_paths:
+        content = content.replace(old_path, new_path)
+        print(f"Replaced {old_path} with {new_path}")
+
+    with open(xml_file, "w", encoding="utf-8") as file:
+        file.write(content)
+
+    print("Start menu XML updated successfully.")
+
+if __name__ == "__main__":
+    xml_file = original_xml
+    extracted_apps_with_paths = extract_app_names_and_paths(xml_file)
+    app_shortcuts = find_shortcut_paths(extracted_apps_with_paths.keys())
+
+    old_new_paths = []
+    for app_name, old_path in extracted_apps_with_paths.items():
+        new_path = app_shortcuts.get(app_name)
+        if new_path:
+            old_new_paths.append((old_path, new_path))
+        else:
+            print(f"Warning: No new path found for {app_name}. Keeping old path.")
+
+    update_xml_paths(xml_file, old_new_paths)
diff --git a/ansible/roles/win_update/vars/main.yml b/ansible/roles/win_update/vars/main.yml
index 47f4512..aba6bed 100644
--- a/ansible/roles/win_update/vars/main.yml
+++ b/ansible/roles/win_update/vars/main.yml
@@ -1,6 +1,5 @@
 ---
-services:
-  - wuauserv
-  - bits
-  - cryptSvc
-  - msiserver
+start_menu_xml: "C:\\eidf\\{{ win_project }}.xml"
+backup_xml: "C:\\eidf\\{{ win_project }}-old.xml"
+script_name: newXML.py
+script_path: "C:\\eidf\\{{ script_name }}"
\ No newline at end of file