diff --git a/app/Jobs/Server/SyncWindowsSettings.php b/app/Jobs/Server/SyncWindowsSettings.php
new file mode 100644
index 00000000000..71521b21417
--- /dev/null
+++ b/app/Jobs/Server/SyncWindowsSettings.php
@@ -0,0 +1,71 @@
+<?php
+namespace Convoy\Jobs\Server;
+
+use Convoy\Models\Server;
+use Convoy\Services\Servers\ServerAuthService;
+use Illuminate\Bus\Queueable;
+use Illuminate\Contracts\Queue\ShouldQueue;
+use Illuminate\Foundation\Bus\Dispatchable;
+use Illuminate\Queue\InteractsWithQueue;
+use Illuminate\Queue\Middleware\SkipIfBatchCancelled;
+use Illuminate\Queue\Middleware\WithoutOverlapping;
+use Illuminate\Queue\SerializesModels;
+
+class SyncWindowsSettings implements ShouldQueue
+{
+    use Dispatchable, InteractsWithQueue, Queueable, SerializesModels;
+
+    public int $tries = 15;
+
+    public int $timeout = 20;
+
+    public function __construct(protected int $serverId, protected string $password)
+    {
+        //
+    }
+
+    public function middleware(): array
+    {
+        return [new SkipIfBatchCancelled(), new WithoutOverlapping(
+            "server.sync-windows-settings#{$this->serverId}",
+        )];
+    }
+
+    public function handle(ServerAuthService $service): void
+    {
+        $server = Server::findOrFail($this->serverId);
+
+        $service->updateWindowsPassword($server, $this->password);
+    }
+
+    /**
+     * Determine the time at which the job should retry.
+     *
+     * @return \DateTime
+     */
+    public function retryAfter(): \DateTime
+    {
+        return now()->addSeconds(20);
+    }
+
+    /**
+     * Determine the time at which the job should timeout.
+     *
+     * @return \DateTime
+     */
+    public function retryUntil(): \DateTime
+    {
+        return now()->addSeconds($this->timeout * $this->tries);
+    }
+
+    /**
+     * Handle a job failure.
+     *
+     * @return void
+     */
+    public function failed(): void
+    {
+        // Mark the job as completed
+        $this->delete();
+    }
+}
\ No newline at end of file
diff --git a/app/Repositories/Proxmox/Server/ProxmoxGuestAgentRepository.php b/app/Repositories/Proxmox/Server/ProxmoxGuestAgentRepository.php
new file mode 100644
index 00000000000..d9752f5f2b4
--- /dev/null
+++ b/app/Repositories/Proxmox/Server/ProxmoxGuestAgentRepository.php
@@ -0,0 +1,61 @@
+<?php
+
+namespace Convoy\Repositories\Proxmox\Server;
+
+use Convoy\Models\Server;
+use Webmozart\Assert\Assert;
+use Convoy\Repositories\Proxmox\ProxmoxRepository;
+use Convoy\Exceptions\Repository\Proxmox\ProxmoxConnectionException;
+
+class ProxmoxGuestAgentRepository extends ProxmoxRepository
+{
+    /**
+     * Get Guest Agent status.
+     *
+     * @return mixed
+     *
+     * @throws ProxmoxConnectionException
+     */
+    public function guestAgentOs()
+    {
+        Assert::isInstanceOf($this->server, Server::class);
+
+        $response = $this->getHttpClient()
+            ->withUrlParameters([
+                'node' => $this->node->cluster,
+                'server' => $this->server->vmid,
+            ])
+            ->get('/api2/json/nodes/{node}/qemu/{server}/agent/get-osinfo')
+            ->json();
+
+        return $this->getData($response);
+    }
+
+    /**
+     * Update Guest Agent password for Administrator user.
+     *
+     * @param string $password
+     * @return mixed
+     *
+     * @throws ProxmoxConnectionException
+     */
+    public function updateGuestAgentPassword(string $username, string $password)
+    {
+        Assert::isInstanceOf($this->server, Server::class);
+
+        $params = [
+            'username' => $username,
+            'password' => $password,
+        ];
+
+        $response = $this->getHttpClient()
+            ->withUrlParameters([
+                'node' => $this->node->cluster,
+                'server' => $this->server->vmid,
+            ])
+            ->post('/api2/json/nodes/{node}/qemu/{server}/agent/set-user-password', $params)
+            ->json();
+
+        return $this->getData($response);
+    }
+}
\ No newline at end of file
diff --git a/app/Services/Servers/ServerAuthService.php b/app/Services/Servers/ServerAuthService.php
index 590948888e1..e53f2defad6 100644
--- a/app/Services/Servers/ServerAuthService.php
+++ b/app/Services/Servers/ServerAuthService.php
@@ -4,20 +4,32 @@
 
 use Convoy\Models\Server;
 use Convoy\Repositories\Proxmox\Server\ProxmoxConfigRepository;
+use Convoy\Repositories\Proxmox\Server\ProxmoxGuestAgentRepository;
 
 class ServerAuthService
 {
-    public function __construct(private ProxmoxConfigRepository $configRepository)
+    public function __construct(private ProxmoxConfigRepository $configRepository, private ProxmoxGuestAgentRepository $guestAgentRepository)
     {
     }
 
     public function updatePassword(Server $server, string $password)
     {
-        // if (!empty($password)) {
-        $this->configRepository->setServer($server)->update(['cipassword' => $password]);
-        // } else {
-        //     $this->configRepository->setServer($server)->update(['delete' => 'cipassword']);
-        // }
+        try {
+            $OsInfo = $this->guestAgentRepository->setServer($server)->guestAgentOs();
+            if (str_contains($OsInfo["result"]["name"], "Windows")) {
+                $username = "Administrator";
+            } else {
+                $username = "root";
+            }
+            $this->guestAgentRepository->setServer($server)->updateGuestAgentPassword($username, $password);
+            $this->configRepository->setServer($server)->update(['cipassword' => $password]);
+        } catch (\Exception $e) {
+            $this->configRepository->setServer($server)->update(['cipassword' => $password]);
+        }
+    }
+
+    public function updateWindowsPassword(Server $server, string $password) {
+        $this->guestAgentRepository->setServer($server)->updateGuestAgentPassword("Administrator", $password);
     }
 
     public function getSSHKeys(Server $server)
@@ -29,10 +41,10 @@ public function getSSHKeys(Server $server)
 
     public function updateSSHKeys(Server $server, ?string $keys)
     {
-        if (! empty($keys)) {
+        if (!empty($keys)) {
             $this->configRepository->setServer($server)->update(['sshkeys' => rawurlencode($keys)]);
         } else {
             $this->configRepository->setServer($server)->update(['delete' => 'sshkeys']);
         }
     }
-}
+}
\ No newline at end of file
diff --git a/app/Services/Servers/ServerBuildDispatchService.php b/app/Services/Servers/ServerBuildDispatchService.php
index 528d81e78fb..bf2e4a312d7 100644
--- a/app/Services/Servers/ServerBuildDispatchService.php
+++ b/app/Services/Servers/ServerBuildDispatchService.php
@@ -15,6 +15,7 @@
 use Convoy\Jobs\Server\SendPowerCommandJob;
 use Convoy\Jobs\Server\WaitUntilVmIsCreatedJob;
 use Convoy\Jobs\Server\WaitUntilVmIsDeletedJob;
+use Convoy\Jobs\Server\SyncWindowsSettings;
 use Convoy\Data\Server\Deployments\ServerDeploymentData;
 
 class ServerBuildDispatchService
@@ -67,11 +68,20 @@ private function getChainedBuildJobs(ServerDeploymentData $deployment): array
             ];
         }
 
-        if (! empty($deployment->account_password)) {
+        $startOnce = false;
+        
+        // TODO: Readd the start_on_completion check
+
+        if (!empty($deployment->account_password)) {
             $jobs[] = new UpdatePasswordJob($deployment->server->id, $deployment->account_password);
+            if (str_contains($deployment->template->name, "Windows")) {
+                $jobs[] = new SendPowerCommandJob($deployment->server->id, PowerAction::START);
+                $startOnce = true;
+                $jobs[] = new SyncWindowsSettings($deployment->server->id, $deployment->account_password);
+            }
         }
 
-        if ($deployment->start_on_completion) {
+        if (!$startOnce) {
             $jobs[] = new SendPowerCommandJob($deployment->server->id, PowerAction::START);
         }
 
@@ -91,4 +101,4 @@ public function getChainedDeleteJobs(Server $server): array
             new WaitUntilVmIsDeletedJob($server->id),
         ];
     }
-}
+}
\ No newline at end of file