diff --git a/Modules/UserManagement/Database/Migrations/2026_08_26_080000_ensure_initial_helpdesk_admin.php b/Modules/UserManagement/Database/Migrations/2026_08_26_080000_ensure_initial_helpdesk_admin.php
new file mode 100644
index 0000000..9c24f9a
--- /dev/null
+++ b/Modules/UserManagement/Database/Migrations/2026_08_26_080000_ensure_initial_helpdesk_admin.php
@@ -0,0 +1,47 @@
+<?php
+
+declare(strict_types=1);
+
+use Illuminate\Database\Migrations\Migration;
+use Illuminate\Support\Facades\DB;
+use Illuminate\Support\Facades\Schema;
+
+return new class extends Migration
+{
+    public function up(): void
+    {
+        if (
+            ! Schema::hasTable('users')
+            || ! Schema::hasColumn('users', 'helpdesk_admin')
+            || ! Schema::hasColumn('users', 'helpdesk_agent')
+        ) {
+            return;
+        }
+
+        // Do nothing when an administrator already exists.
+        if (DB::table('users')->where('helpdesk_admin', true)->exists()) {
+            return;
+        }
+
+        // Bootstrap the oldest account as the initial administrator.
+        // From this point onward administrators are managed through User Management.
+        $initialUserId = DB::table('users')->orderBy('id')->value('id');
+
+        if ($initialUserId === null) {
+            return;
+        }
+
+        DB::table('users')
+            ->where('id', $initialUserId)
+            ->update([
+                'helpdesk_admin' => true,
+                'helpdesk_agent' => true,
+                'updated_at' => now(),
+            ]);
+    }
+
+    public function down(): void
+    {
+        // Intentionally non-destructive. Never silently remove an administrator.
+    }
+};
diff --git a/resources/themes/backend/views/layouts/app/sidebar.blade.php b/resources/themes/backend/views/layouts/app/sidebar.blade.php
index 5edc30b..19b1fdc 100644
--- a/resources/themes/backend/views/layouts/app/sidebar.blade.php
+++ b/resources/themes/backend/views/layouts/app/sidebar.blade.php
@@ -4,7 +4,10 @@
 <body class="hd-app-body">
 @php
     $user = auth()->user();
-    $isAdmin = (method_exists($user, 'isHelpdeskAdmin') && $user->isHelpdeskAdmin()) || (method_exists($user, 'isAdmin') && $user->isAdmin()) || (bool) ($user->helpdesk_admin ?? false);
+    $isAdmin =
+        (bool) ($user?->helpdesk_admin ?? false)
+        || ($user && method_exists($user, 'isHelpdeskAdmin') && $user->isHelpdeskAdmin())
+        || ($user && method_exists($user, 'isAdmin') && $user->isAdmin());
     $roleLabel = $isAdmin ? 'Administrator' : ((method_exists($user, 'isHelpdeskAgent') && $user->isHelpdeskAgent()) || (bool) ($user->helpdesk_agent ?? false) ? 'Agent' : 'User');
 @endphp
 <div class="hd-app-shell" data-hd-shell>
@@ -39,20 +42,37 @@
 
     <aside class="hd-shell-sidebar" data-hd-sidebar>
         <nav class="hd-shell-nav" aria-label="Primary navigation">
-            <div class="hd-nav-section"><div class="hd-nav-heading">Platform</div>
-                <a class="hd-nav-link {{ request()->routeIs('dashboard') ? 'is-active' : '' }}" href="{{ route('dashboard') }}" wire:navigate>
-                    <i class="fa-solid fa-house"></i><span>Dashboard</span>
+            <div class="hd-nav-section">
+                <div class="hd-nav-heading">Platform</div>
+
+                <a
+                    class="hd-nav-link {{ request()->routeIs('dashboard') ? 'is-active' : '' }}"
+                    href="{{ route('dashboard') }}"
+                    wire:navigate
+                >
+                    <i class="fa-solid fa-house"></i>
+                    <span>Dashboard</span>
                 </a>
 
-                <a class="hd-nav-link {{ request()->is('admin/users') || request()->is('admin/users/create') || request()->is('admin/users/*/edit') ? 'is-active' : '' }}"
-                   href="{{ url('/admin/users') }}" wire:navigate>
-                    <i class="fa-solid fa-users"></i><span>Users</span>
-                </a>
+                @if ($isAdmin)
+                    <a
+                        class="hd-nav-link {{ request()->is('admin/users') || request()->is('admin/users/create') || request()->is('admin/users/*/edit') ? 'is-active' : '' }}"
+                        href="{{ url('/admin/users') }}"
+                        wire:navigate
+                    >
+                        <i class="fa-solid fa-users"></i>
+                        <span>Users</span>
+                    </a>
 
-                <a class="hd-nav-link {{ request()->is('admin/users/roles') ? 'is-active' : '' }}"
-                   href="{{ url('/admin/users/roles') }}" wire:navigate>
-                    <i class="fa-solid fa-shield-halved"></i><span>Roles & Permissions</span>
-                </a>
+                    <a
+                        class="hd-nav-link {{ request()->is('admin/users/roles') ? 'is-active' : '' }}"
+                        href="{{ url('/admin/users/roles') }}"
+                        wire:navigate
+                    >
+                        <i class="fa-solid fa-shield-halved"></i>
+                        <span>Roles &amp; Permissions</span>
+                    </a>
+                @endif
             </div>
 
             <div class="hd-nav-section"><div class="hd-nav-heading">Helpdesk</div>
@@ -66,6 +86,12 @@
                 @if(Route::has('documentation.categories.index'))<a class="hd-nav-link {{ request()->routeIs('documentation.categories.*') ? 'is-active' : '' }}" href="{{ route('documentation.categories.index') }}" wire:navigate><i class="fa-regular fa-folder"></i><span>Categories</span></a>@endif
             </div>
             @endif
+            @if($isAdmin && Route::has('user-management.index'))
+            <div class="hd-nav-section"><div class="hd-nav-heading">Users</div>
+                <a class="hd-nav-link {{ request()->routeIs('user-management.index') || request()->routeIs('user-management.create') || request()->routeIs('user-management.edit') ? 'is-active' : '' }}" href="{{ route('user-management.index') }}" wire:navigate><i class="fa-solid fa-users"></i><span>Users</span></a>
+                <a class="hd-nav-link {{ request()->routeIs('user-management.roles') ? 'is-active' : '' }}" href="{{ route('user-management.roles') }}" wire:navigate><i class="fa-solid fa-shield-halved"></i><span>Roles & Permissions</span></a>
+            </div>
+            @endif
         </nav>
         <div class="hd-sidebar-resizer" data-hd-sidebar-resizer title="Drag to resize sidebar"><span></span></div>
     </aside>