diff --git a/app/Http/Controllers/TelegramWebhookController.php b/app/Http/Controllers/TelegramWebhookController.php
index 3d7c7dd..82a31e2 100644
--- a/app/Http/Controllers/TelegramWebhookController.php
+++ b/app/Http/Controllers/TelegramWebhookController.php
@@ -4,10 +4,25 @@ namespace App\Http\Controllers;
 
 use App\Services\TelegramBotService;
 use Illuminate\Http\Request;
+use Illuminate\Support\Facades\Log;
 
 class TelegramWebhookController extends Controller
 {
     public function handle(Request $request)
+    {
+        try {
+            return $this->process($request);
+        } catch (\Throwable $e) {
+            Log::error('[TelegramWebhook] Uncaught exception: ' . $e->getMessage(), [
+                'trace' => $e->getTraceAsString(),
+                'body'  => $request->all(),
+            ]);
+            // Always return 200 so Telegram doesn't retry
+            return response()->json(['ok' => true]);
+        }
+    }
+
+    private function process(Request $request)
     {
         $update = $request->all();
         $bot    = new TelegramBotService();
@@ -57,3 +72,4 @@ class TelegramWebhookController extends Controller
         return response()->json(['ok' => true]);
     }
 }
+
diff --git a/app/Services/TelegramBotService.php b/app/Services/TelegramBotService.php
index 6bd6468..cb81c79 100644
--- a/app/Services/TelegramBotService.php
+++ b/app/Services/TelegramBotService.php
@@ -342,7 +342,13 @@ class TelegramBotService
             return;
         }
 
-        $user = User::whereRaw('LOWER(email) = ?', [$email])->first();
+        try {
+            $user = User::whereRaw('LOWER(email) = ?', [$email])->first();
+        } catch (\Throwable $e) {
+            Log::error('[TelegramBot] processEmail DB error: ' . $e->getMessage());
+            $this->send($chatId, "⚠️ Error de conexión. Escribe tu correo de nuevo:");
+            return;
+        }
 
         if (! $user) {
             $this->setState($chatId, [
@@ -356,16 +362,22 @@ class TelegramBotService
             return;
         }
 
-        $contact = ChatContact::where('canal', 'telegram')->where('canal_id', $chatId)->first();
-        if ($contact) {
-            $contact->update(['user_id' => $user->id, 'nombre' => $user->name]);
-        } else {
-            $contact = ChatContact::create([
-                'canal'    => 'telegram',
-                'canal_id' => $chatId,
-                'nombre'   => $user->name,
-                'user_id'  => $user->id,
-            ]);
+        try {
+            $contact = ChatContact::where('canal', 'telegram')->where('canal_id', (string) $chatId)->first();
+            if ($contact) {
+                $contact->update(['user_id' => $user->id, 'nombre' => $user->name]);
+            } else {
+                $contact = ChatContact::create([
+                    'canal'    => 'telegram',
+                    'canal_id' => (string) $chatId,
+                    'nombre'   => $user->name,
+                    'user_id'  => $user->id,
+                ]);
+            }
+        } catch (\Throwable $e) {
+            Log::error('[TelegramBot] processEmail contact error: ' . $e->getMessage());
+            $this->send($chatId, "⚠️ Error interno. Escribe tu correo de nuevo:");
+            return;
         }
 
         $this->sendOtp($chatId, $contact, $user);
@@ -376,9 +388,11 @@ class TelegramBotService
         $codigo = (string) random_int(100000, 999999);
         Cache::put("chat_otp_{$contact->id}", $codigo, now()->addMinutes(10));
 
+        $mailEnviado = true;
         try {
             Mail::to($user->email)->send(new ChatOtpMail($codigo, $user->name));
         } catch (\Throwable $e) {
+            $mailEnviado = false;
             Log::warning('[TelegramOTP] Error enviando correo: ' . $e->getMessage());
         }
 
@@ -389,7 +403,16 @@ class TelegramBotService
         ]);
 
         $masked = $this->maskEmail($user->email);
-        $this->send($chatId, "✉️ Te enviamos un código a *{$masked}*.\n\nEscribe el código de 6 dígitos:");
+
+        if ($mailEnviado) {
+            $this->send($chatId, "✉️ Te enviamos un código a *{$masked}*.\n\nEscribe el código de 6 dígitos:");
+        } else {
+            $this->send($chatId,
+                "✉️ Código generado para *{$masked}*.\n\n" .
+                "⚠️ Hubo un problema enviando el correo. Revisa tu bandeja o escribe /cancelar para intentar de nuevo.\n\n" .
+                "Si lo recibiste, escribe el código de 6 dígitos:"
+            );
+        }
     }
 
     private function processOtp(string $chatId, string $text): void