diff --git a/app/Jobs/ApplicationDeploymentJob.php b/app/Jobs/ApplicationDeploymentJob.php
index 84f362519..b593ea836 100644
--- a/app/Jobs/ApplicationDeploymentJob.php
+++ b/app/Jobs/ApplicationDeploymentJob.php
@@ -175,6 +175,8 @@ class ApplicationDeploymentJob implements ShouldBeEncrypted, ShouldQueue
 
     private Collection|string $build_secrets;
 
+    private ?string $github_access_token = null;
+
     public function tags()
     {
         // Do not remove this one, it needs to properly identify which worker is running the job
@@ -212,6 +214,16 @@ class ApplicationDeploymentJob implements ShouldBeEncrypted, ShouldQueue
         if ($source) {
             $this->source = $source->getMorphClass()::where('id', $this->application->source->id)->first();
         }
+
+        // Pre-generate GitHub installation token once to avoid multiple API calls during deployment
+        if ($this->source instanceof GithubApp && ! $this->source->is_public) {
+            try {
+                $this->github_access_token = generateGithubInstallationToken($this->source);
+            } catch (\Exception $e) {
+                // Token generation will be retried later if needed
+                $this->github_access_token = null;
+            }
+        }
         $this->server = Server::find($this->application_deployment_queue->server_id);
         $this->timeout = $this->server->settings->dynamic_timeout;
         $this->destination = $this->server->destinations()->where('id', $this->application_deployment_queue->destination_id)->first();
@@ -2065,7 +2077,7 @@ class ApplicationDeploymentJob implements ShouldBeEncrypted, ShouldQueue
     private function check_git_if_build_needed()
     {
         if (is_object($this->source) && $this->source->getMorphClass() === \App\Models\GithubApp::class && $this->source->is_public === false) {
-            $repository = githubApi($this->source, "repos/{$this->customRepository}");
+            $repository = githubApi($this->source, "repos/{$this->customRepository}", token: $this->github_access_token);
             $data = data_get($repository, 'data');
             $repository_project_id = data_get($data, 'id');
             if (isset($repository_project_id)) {
@@ -2190,7 +2202,8 @@ class ApplicationDeploymentJob implements ShouldBeEncrypted, ShouldQueue
             deployment_uuid: $this->deployment_uuid,
             pull_request_id: $this->pull_request_id,
             git_type: $this->git_type,
-            commit: $this->commit
+            commit: $this->commit,
+            github_access_token: $this->github_access_token
         );
 
         return $commands;
diff --git a/app/Models/Application.php b/app/Models/Application.php
index 2eab8df20..a72d2e2b8 100644
--- a/app/Models/Application.php
+++ b/app/Models/Application.php
@@ -1143,7 +1143,7 @@ class Application extends BaseModel
         }
     }
 
-    public function generateGitLsRemoteCommands(string $deployment_uuid, bool $exec_in_docker = true)
+    public function generateGitLsRemoteCommands(string $deployment_uuid, bool $exec_in_docker = true, ?string $github_access_token = null)
     {
         $branch = $this->git_branch;
         ['repository' => $customRepository, 'port' => $customPort] = $this->customRepository();
@@ -1163,7 +1163,8 @@ class Application extends BaseModel
                     $fullRepoUrl = "{$this->source->html_url}/{$customRepository}";
                     $base_command = "{$base_command} {$escapedRepoUrl}";
                 } else {
-                    $github_access_token = generateGithubInstallationToken($this->source);
+                    // Use provided token or generate a new one
+                    $github_access_token = $github_access_token ?? generateGithubInstallationToken($this->source);
 
                     if ($exec_in_docker) {
                         $repoUrl = "$source_html_url_scheme://x-access-token:$github_access_token@$source_html_url_host/{$customRepository}.git";
@@ -1250,7 +1251,7 @@ class Application extends BaseModel
         }
     }
 
-    public function generateGitImportCommands(string $deployment_uuid, int $pull_request_id = 0, ?string $git_type = null, bool $exec_in_docker = true, bool $only_checkout = false, ?string $custom_base_dir = null, ?string $commit = null)
+    public function generateGitImportCommands(string $deployment_uuid, int $pull_request_id = 0, ?string $git_type = null, bool $exec_in_docker = true, bool $only_checkout = false, ?string $custom_base_dir = null, ?string $commit = null, ?string $github_access_token = null)
     {
         $branch = $this->git_branch;
         ['repository' => $customRepository, 'port' => $customPort] = $this->customRepository();
@@ -1301,7 +1302,8 @@ class Application extends BaseModel
                         $commands->push($git_clone_command);
                     }
                 } else {
-                    $github_access_token = generateGithubInstallationToken($this->source);
+                    // Use provided token or generate a new one
+                    $github_access_token = $github_access_token ?? generateGithubInstallationToken($this->source);
                     if ($exec_in_docker) {
                         $repoUrl = "$source_html_url_scheme://x-access-token:$github_access_token@$source_html_url_host/{$customRepository}.git";
                         $escapedRepoUrl = escapeshellarg($repoUrl);
diff --git a/app/Providers/AppServiceProvider.php b/app/Providers/AppServiceProvider.php
index 717daf2a2..40ed73829 100644
--- a/app/Providers/AppServiceProvider.php
+++ b/app/Providers/AppServiceProvider.php
@@ -66,16 +66,18 @@ class AppServiceProvider extends ServiceProvider
     private function configureGitHubHttp(): void
     {
         Http::macro('GitHub', function (string $api_url, ?string $github_access_token = null) {
+            $timeout = config('constants.github.api_timeout', 30);
+
             if ($github_access_token) {
                 return Http::withHeaders([
                     'X-GitHub-Api-Version' => '2022-11-28',
                     'Accept' => 'application/vnd.github.v3+json',
                     'Authorization' => "Bearer $github_access_token",
-                ])->baseUrl($api_url);
+                ])->baseUrl($api_url)->timeout($timeout);
             } else {
                 return Http::withHeaders([
                     'Accept' => 'application/vnd.github.v3+json',
-                ])->baseUrl($api_url);
+                ])->baseUrl($api_url)->timeout($timeout);
             }
         });
     }
diff --git a/bootstrap/helpers/github.php b/bootstrap/helpers/github.php
index 4a61960fb..b8ea9a585 100644
--- a/bootstrap/helpers/github.php
+++ b/bootstrap/helpers/github.php
@@ -14,7 +14,19 @@ use Lcobucci\JWT\Token\Builder;
 
 function generateGithubToken(GithubApp $source, string $type)
 {
-    $response = Http::get("{$source->api_url}/zen");
+    $timeout = config('constants.github.api_timeout', 30);
+
+    $response = Http::timeout($timeout)
+        ->retry(3, 200, throw: false)
+        ->get("{$source->api_url}/zen");
+
+    if (! $response->successful()) {
+        throw new \Exception(
+            'Failed to connect to GitHub API to sync time. '.
+            'Please check your network connection and try again.'
+        );
+    }
+
     $serverTime = CarbonImmutable::now()->setTimezone('UTC');
     $githubTime = Carbon::parse($response->header('date'));
     $timeDiff = abs($serverTime->diffInSeconds($githubTime));
@@ -44,11 +56,13 @@ function generateGithubToken(GithubApp $source, string $type)
 
     return match ($type) {
         'jwt' => $jwt,
-        'installation' => (function () use ($source, $jwt) {
+        'installation' => (function () use ($source, $jwt, $timeout) {
             $response = Http::withHeaders([
                 'Authorization' => "Bearer $jwt",
                 'Accept' => 'application/vnd.github.machine-man-preview+json',
-            ])->post("{$source->api_url}/app/installations/{$source->installation_id}/access_tokens");
+            ])->timeout($timeout)
+                ->retry(3, 200, throw: false)
+                ->post("{$source->api_url}/app/installations/{$source->installation_id}/access_tokens");
 
             if (! $response->successful()) {
                 $error = data_get($response->json(), 'message', 'no error message found');
@@ -74,7 +88,7 @@ function generateGithubJwt(GithubApp $source)
     return generateGithubToken($source, 'jwt');
 }
 
-function githubApi(GithubApp|GitlabApp|null $source, string $endpoint, string $method = 'get', ?array $data = null, bool $throwError = true)
+function githubApi(GithubApp|GitlabApp|null $source, string $endpoint, string $method = 'get', ?array $data = null, bool $throwError = true, ?string $token = null)
 {
     if (is_null($source)) {
         throw new \Exception('Source is required for API calls');
@@ -87,7 +101,8 @@ function githubApi(GithubApp|GitlabApp|null $source, string $endpoint, string $m
     if ($source->is_public) {
         $response = Http::GitHub($source->api_url)->$method($endpoint);
     } else {
-        $token = generateGithubInstallationToken($source);
+        // Use provided token or generate a new one
+        $token = $token ?? generateGithubInstallationToken($source);
         if ($data && in_array(strtolower($method), ['post', 'patch', 'put'])) {
             $response = Http::GitHub($source->api_url, $token)->$method($endpoint, $data);
         } else {
diff --git a/config/constants.php b/config/constants.php
index 499076e85..67c967de2 100644
--- a/config/constants.php
+++ b/config/constants.php
@@ -59,6 +59,10 @@ return [
         'minimum_required_version' => '24.0',
     ],
 
+    'github' => [
+        'api_timeout' => env('GITHUB_API_TIMEOUT', 30),
+    ],
+
     'ssh' => [
         'mux_enabled' => env('MUX_ENABLED', env('SSH_MUX_ENABLED', true)),
         'mux_persist_time' => env('SSH_MUX_PERSIST_TIME', 3600),