diff --git a/app/Http/Middleware/WebhookRateLimit.php b/app/Http/Middleware/WebhookRateLimit.php
new file mode 100644
index 0000000..31d49a2
--- /dev/null
+++ b/app/Http/Middleware/WebhookRateLimit.php
@@ -0,0 +1,65 @@
+<?php
+
+namespace App\Http\Middleware;
+
+use Closure;
+use Illuminate\Http\Request;
+use Illuminate\Support\Facades\Cache;
+use Symfony\Component\HttpFoundation\Response;
+
+class WebhookRateLimit
+{
+    /**
+     * Handle an incoming request.
+     *
+     * @param  Closure(Request):Response  $next
+     */
+    public function handle(Request $request, Closure $next): Response
+    {
+        $provider = $request->route('provider');
+        $clientIp = $request->ip();
+
+        // Rate limits per provider (requests per minute)
+        $rateLimits = [
+            'polar' => 60,        // Polar: 60 requests per minute
+            'stripe' => 100,      // Stripe: 100 requests per minute
+            'lemon_squeezy' => 60, // Lemon Squeezy: 60 requests per minute
+            'oxapay' => 30,       // OxaPay: 30 requests per minute
+            'crypto' => 20,       // Crypto: 20 requests per minute
+        ];
+
+        $rateLimit = $rateLimits[$provider] ?? 30; // Default: 30 requests per minute
+
+        // Cache key for rate limiting
+        $key = "webhook_rate_limit:{$provider}:{$clientIp}";
+
+        // Use Laravel's Cache atomic increment for rate limiting
+        $current = Cache::increment($key, 1, now()->addMinutes(1));
+
+        // Check if rate limit exceeded
+        if ($current > $rateLimit) {
+            // Log rate limit violation
+            \Log::warning('Webhook rate limit exceeded', [
+                'provider' => $provider,
+                'ip' => $clientIp,
+                'current' => $current,
+                'limit' => $rateLimit,
+                'user_agent' => $request->userAgent(),
+                'request_size' => strlen($request->getContent()),
+            ]);
+
+            return response()->json([
+                'error' => 'Rate limit exceeded',
+                'message' => 'Too many webhook requests. Please try again later.',
+                'retry_after' => 60,
+            ], 429)->header('Retry-After', 60);
+        }
+
+        // Add rate limit headers
+        $response = $next($request);
+        $response->headers->set('X-RateLimit-Limit', $rateLimit);
+        $response->headers->set('X-RateLimit-Remaining', max(0, $rateLimit - $current));
+
+        return $response;
+    }
+}
diff --git a/app/Models/PaymentProvider.php b/app/Models/PaymentProvider.php
index 60ffcde..3b71a30 100644
--- a/app/Models/PaymentProvider.php
+++ b/app/Models/PaymentProvider.php
@@ -2,10 +2,13 @@
 
 namespace App\Models;
 
+use Illuminate\Database\Eloquent\Factories\HasFactory;
 use Illuminate\Database\Eloquent\Model;
 
 class PaymentProvider extends Model
 {
+    use HasFactory;
+
     protected $fillable = [
         'name',
         'display_name',
diff --git a/app/Models/Subscription.php b/app/Models/Subscription.php
index 3f6a01e..a6e25e7 100644
--- a/app/Models/Subscription.php
+++ b/app/Models/Subscription.php
@@ -3,11 +3,14 @@
 namespace App\Models;
 
 use App\Services\Payments\PaymentOrchestrator;
+use Illuminate\Database\Eloquent\Factories\HasFactory;
 use Illuminate\Database\Eloquent\Model;
 use Illuminate\Support\Facades\Log;
 
 class Subscription extends Model
 {
+    use HasFactory;
+
     protected $fillable = [
         'user_id',
         'type',
@@ -49,6 +52,16 @@ class Subscription extends Model
         'order_created_at',
         'order_paid_at',
         'provider_checkout_id',
+        'resume_reason',
+        'trial_ended_at',
+        'trial_converted_to',
+        'subscription_id_fetched_at',
+        'polar_dates',
+        'customer_state_changed_at',
+        'polar_subscription_data',
+        'customer_metadata',
+        'trial_will_end_sent_at',
+        'pause_reason',
     ];
 
     protected $casts = [
diff --git a/app/Services/Payments/Providers/PolarProvider.php b/app/Services/Payments/Providers/PolarProvider.php
index 9766bc2..4256d5a 100644
--- a/app/Services/Payments/Providers/PolarProvider.php
+++ b/app/Services/Payments/Providers/PolarProvider.php
@@ -7,6 +7,8 @@ use App\Models\PaymentProvider as PaymentProviderModel;
 use App\Models\Plan;
 use App\Models\Subscription;
 use App\Models\User;
+use App\Services\Webhooks\WebhookFactory;
+use App\Services\Webhooks\WebhookVerificationException;
 use Carbon\Carbon;
 use Illuminate\Http\Request;
 use Illuminate\Support\Facades\Http;
@@ -598,10 +600,31 @@ class PolarProvider implements PaymentProviderContract
 
             $webhookData = json_decode($payload, true);
             $eventType = $webhookData['type'] ?? 'unknown';
+            $webhookId = $webhookData['id'] ?? null;
+
+            // Check for idempotency - prevent duplicate processing
+            if ($webhookId && $this->isWebhookProcessed($webhookId)) {
+                Log::info('Polar webhook already processed, skipping', [
+                    'webhook_id' => $webhookId,
+                    'event_type' => $eventType,
+                ]);
+
+                return [
+                    'event_type' => $eventType,
+                    'processed' => true,
+                    'idempotent' => true,
+                    'data' => [
+                        'webhook_id' => $webhookId,
+                        'message' => 'Webhook already processed',
+                    ],
+                ];
+            }
 
             $result = [
                 'event_type' => $eventType,
                 'processed' => false,
+                'idempotent' => false,
+                'webhook_id' => $webhookId,
                 'data' => [],
             ];
 
@@ -627,6 +650,18 @@ class PolarProvider implements PaymentProviderContract
                 case 'subscription.cancelled':
                     $result = $this->handleSubscriptionCancelled($webhookData);
                     break;
+                case 'subscription.paused':
+                    $result = $this->handleSubscriptionPaused($webhookData);
+                    break;
+                case 'subscription.resumed':
+                    $result = $this->handleSubscriptionResumed($webhookData);
+                    break;
+                case 'subscription.trial_will_end':
+                    $result = $this->handleSubscriptionTrialWillEnd($webhookData);
+                    break;
+                case 'subscription.trial_ended':
+                    $result = $this->handleSubscriptionTrialEnded($webhookData);
+                    break;
                 case 'customer.state_changed':
                     $result = $this->handleCustomerStateChanged($webhookData);
                     break;
@@ -634,11 +669,18 @@ class PolarProvider implements PaymentProviderContract
                     Log::info('Unhandled Polar webhook event', ['event_type' => $eventType]);
             }
 
+            // Mark webhook as processed if it has an ID and was successfully processed
+            if ($webhookId && ($result['processed'] ?? false)) {
+                $this->markWebhookAsProcessed($webhookId, $eventType, $result);
+            }
+
             return $result;
 
         } catch (\Exception $e) {
             Log::error('Polar webhook processing failed', [
                 'error' => $e->getMessage(),
+                'webhook_id' => $webhookId ?? 'none',
+                'event_type' => $eventType ?? 'unknown',
                 'payload' => $request->getContent(),
             ]);
             throw $e;
@@ -648,20 +690,63 @@ class PolarProvider implements PaymentProviderContract
     public function validateWebhook(Request $request): bool
     {
         try {
-            $signature = $request->header('Polar-Signature');
-            $payload = $request->getContent();
+            // In sandbox mode, bypass validation for development
+//            if ($this->sandbox) {
+//                Log::info('Polar webhook validation bypassed in sandbox mode', [
+//                    'sandbox_bypass' => true,
+//                ]);
+//
+//                return true;
+//            }
+
+            // Check if we have a webhook secret
+            if (empty($this->webhookSecret)) {
+                Log::warning('Polar webhook validation failed: missing webhook secret');
 
-            if (! $signature || ! $this->webhookSecret) {
                 return false;
             }
 
-            $expectedSignature = hash_hmac('sha256', $payload, $this->webhookSecret);
+            // Extract headers
+            $headers = [
+                'webhook-id' => $request->header('webhook-id'),
+                'webhook-timestamp' => $request->header('webhook-timestamp'),
+                'webhook-signature' => $request->header('webhook-signature'),
+            ];
 
-            return hash_equals($signature, $expectedSignature);
+            $payload = $request->getContent();
 
-        } catch (\Exception $e) {
+            Log::info('Polar webhook validation attempt using Standard Webhooks', [
+                'webhook_id' => $headers['webhook-id'],
+                'has_signature' => ! empty($headers['webhook-signature']),
+                'has_timestamp' => ! empty($headers['webhook-timestamp']),
+                'payload_length' => strlen($payload),
+            ]);
+
+            // Create Standard Webhooks validator for Polar
+            $webhook = WebhookFactory::createPolar($this->webhookSecret);
+
+            // Verify the webhook
+            $result = $webhook->verify($payload, $headers);
+
+            Log::info('Polar webhook validation successful using Standard Webhooks', [
+                'webhook_id' => $headers['webhook-id'],
+                'payload_size' => strlen($payload),
+            ]);
+
+            return true;
+
+        } catch (WebhookVerificationException $e) {
             Log::warning('Polar webhook validation failed', [
                 'error' => $e->getMessage(),
+                'webhook_id' => $request->header('webhook-id'),
+            ]);
+
+            return false;
+
+        } catch (\Exception $e) {
+            Log::error('Polar webhook validation error', [
+                'error' => $e->getMessage(),
+                'trace' => $e->getTraceAsString(),
             ]);
 
             return false;
@@ -837,15 +922,15 @@ class PolarProvider implements PaymentProviderContract
                     ]);
 
                     return $customer;
-                } else {
-                    Log::warning('Stored Polar customer ID not found, will create new one', [
-                        'user_id' => $user->id,
-                        'polar_cust_id' => $user->polar_cust_id,
-                        'status_code' => $response->status(),
-                    ]);
-                    // Clear the invalid ID and continue to create new customer
-                    $user->update(['polar_cust_id' => null]);
                 }
+
+                Log::warning('Stored Polar customer ID not found, will create new one', [
+                    'user_id' => $user->id,
+                    'polar_cust_id' => $user->polar_cust_id,
+                    'status_code' => $response->status(),
+                ]);
+                // Clear the invalid ID and continue to create new customer
+                $user->update(['polar_cust_id' => null]);
             } catch (\Exception $e) {
                 Log::warning('Failed to retrieve stored Polar customer, will create new one', [
                     'user_id' => $user->id,
@@ -1086,7 +1171,7 @@ class PolarProvider implements PaymentProviderContract
     // Webhook handlers
     protected function handleCheckoutCreated(array $webhookData): array
     {
-        $checkout = $webhookData['data']['object'];
+        $checkout = $webhookData['data'];
 
         // Update local subscription with checkout ID
         Subscription::where('provider_subscription_id', $checkout['id'])->update([
@@ -1112,7 +1197,7 @@ class PolarProvider implements PaymentProviderContract
 
     protected function handleOrderCreated(array $webhookData): array
     {
-        $order = $webhookData['data']['object'];
+        $order = $webhookData['data'];
 
         // Find subscription by checkout ID or customer metadata
         $subscription = Subscription::where('provider', 'polar')
@@ -1146,7 +1231,7 @@ class PolarProvider implements PaymentProviderContract
 
     protected function handleOrderPaid(array $webhookData): array
     {
-        $order = $webhookData['data']['object'];
+        $order = $webhookData['data'];
 
         // Find and activate subscription
         $subscription = Subscription::where('provider', 'polar')
@@ -1181,24 +1266,50 @@ class PolarProvider implements PaymentProviderContract
 
     protected function handleSubscriptionCreated(array $webhookData): array
     {
-        $polarSubscription = $webhookData['data']['object'];
+        $polarSubscription = $webhookData['data'];
 
-        // Find and update local subscription using checkout_id
-        $localSubscription = Subscription::where('provider', 'polar')
-            ->where('provider_checkout_id', $polarSubscription['checkout_id'])
-            ->first();
+        // Find subscription using both subscription ID and checkout ID fallback
+        $localSubscription = $this->findSubscriptionByPolarId(
+            $polarSubscription['id'],
+            $polarSubscription['checkout_id'] ?? null
+        );
 
         if ($localSubscription) {
-            $localSubscription->update([
-                'stripe_id' => $polarSubscription['id'],
+            $updateData = [
                 'provider_subscription_id' => $polarSubscription['id'],
                 'status' => $polarSubscription['status'],
-                'starts_at' => Carbon::parse($polarSubscription['current_period_start']),
-                'ends_at' => Carbon::parse($polarSubscription['current_period_end']),
                 'provider_data' => array_merge($localSubscription->provider_data ?? [], [
                     'polar_subscription' => $polarSubscription,
                     'activated_at' => now()->toISOString(),
                 ]),
+            ];
+
+            // Parse dates if available
+            if (! empty($polarSubscription['current_period_start'])) {
+                $updateData['starts_at'] = Carbon::parse($polarSubscription['current_period_start']);
+            }
+            if (! empty($polarSubscription['current_period_end'])) {
+                $updateData['ends_at'] = Carbon::parse($polarSubscription['current_period_end']);
+            }
+            if (! empty($polarSubscription['trial_end'])) {
+                $updateData['trial_ends_at'] = Carbon::parse($polarSubscription['trial_end']);
+            }
+            if (! empty($polarSubscription['cancelled_at'])) {
+                $updateData['cancelled_at'] = Carbon::parse($polarSubscription['cancelled_at']);
+            }
+
+            $localSubscription->update($updateData);
+
+            Log::info('Polar subscription created/updated via webhook', [
+                'local_subscription_id' => $localSubscription->id,
+                'polar_subscription_id' => $polarSubscription['id'],
+                'checkout_id' => $polarSubscription['checkout_id'] ?? null,
+                'status' => $polarSubscription['status'],
+            ]);
+        } else {
+            Log::warning('Subscription not found for Polar subscription.created webhook', [
+                'polar_subscription_id' => $polarSubscription['id'],
+                'checkout_id' => $polarSubscription['checkout_id'] ?? null,
             ]);
         }
 
@@ -1208,30 +1319,54 @@ class PolarProvider implements PaymentProviderContract
             'data' => [
                 'subscription_id' => $polarSubscription['id'],
                 'status' => $polarSubscription['status'],
+                'local_subscription_id' => $localSubscription?->id,
             ],
         ];
     }
 
     protected function handleSubscriptionActive(array $webhookData): array
     {
-        $polarSubscription = $webhookData['data']['object'];
+        $polarSubscription = $webhookData['data'];
 
-        Subscription::where('provider', 'polar')
-            ->where('provider_subscription_id', $polarSubscription['id'])
-            ->update([
+        // Find subscription using both subscription ID and checkout ID fallback
+        $localSubscription = $this->findSubscriptionByPolarId(
+            $polarSubscription['id'],
+            $polarSubscription['checkout_id'] ?? null
+        );
+
+        if ($localSubscription) {
+            $updateData = [
+                'status' => 'active',
+                'provider_data' => array_merge($localSubscription->provider_data ?? [], [
+                    'polar_subscription' => $polarSubscription,
+                    'activated_at' => now()->toISOString(),
+                ]),
+            ];
+
+            // Parse dates if available
+            if (! empty($polarSubscription['current_period_start'])) {
+                $updateData['starts_at'] = Carbon::parse($polarSubscription['current_period_start']);
+            }
+            if (! empty($polarSubscription['current_period_end'])) {
+                $updateData['ends_at'] = Carbon::parse($polarSubscription['current_period_end']);
+            }
+            if (! empty($polarSubscription['trial_end'])) {
+                $updateData['trial_ends_at'] = Carbon::parse($polarSubscription['trial_end']);
+            }
+
+            $localSubscription->update($updateData);
+
+            Log::info('Polar subscription activated via webhook', [
+                'local_subscription_id' => $localSubscription->id,
+                'polar_subscription_id' => $polarSubscription['id'],
                 'status' => 'active',
-                'starts_at' => Carbon::parse($polarSubscription['current_period_start']),
-                'ends_at' => Carbon::parse($polarSubscription['current_period_end']),
-                'provider_data' => array_merge(
-                    Subscription::where('provider', 'polar')
-                        ->where('provider_subscription_id', $polarSubscription['id'])
-                        ->first()?->provider_data ?? [],
-                    [
-                        'polar_subscription' => $polarSubscription,
-                        'activated_at' => now()->toISOString(),
-                    ]
-                ),
             ]);
+        } else {
+            Log::warning('Subscription not found for Polar subscription.active webhook', [
+                'polar_subscription_id' => $polarSubscription['id'],
+                'checkout_id' => $polarSubscription['checkout_id'] ?? null,
+            ]);
+        }
 
         return [
             'event_type' => 'subscription.active',
@@ -1245,17 +1380,53 @@ class PolarProvider implements PaymentProviderContract
 
     protected function handleSubscriptionUpdated(array $webhookData): array
     {
-        $polarSubscription = $webhookData['data']['object'];
+        $polarSubscription = $webhookData['data'];
 
-        Subscription::where('provider', 'polar')
-            ->where('provider_subscription_id', $polarSubscription['id'])
-            ->update([
+        // Find subscription using both subscription ID and checkout ID fallback
+        $localSubscription = $this->findSubscriptionByPolarId(
+            $polarSubscription['id'],
+            $polarSubscription['checkout_id'] ?? null
+        );
+
+        if ($localSubscription) {
+            $updateData = [
                 'status' => $polarSubscription['status'],
-                'provider_data' => [
+                'provider_data' => array_merge($localSubscription->provider_data ?? [], [
                     'polar_subscription' => $polarSubscription,
                     'updated_at' => now()->toISOString(),
-                ],
+                ]),
+            ];
+
+            // Parse dates if available
+            if (! empty($polarSubscription['current_period_start'])) {
+                $updateData['starts_at'] = Carbon::parse($polarSubscription['current_period_start']);
+            }
+            if (! empty($polarSubscription['current_period_end'])) {
+                $updateData['ends_at'] = Carbon::parse($polarSubscription['current_period_end']);
+            }
+            if (! empty($polarSubscription['trial_end'])) {
+                $updateData['trial_ends_at'] = Carbon::parse($polarSubscription['trial_end']);
+            }
+            if (! empty($polarSubscription['cancelled_at'])) {
+                $updateData['cancelled_at'] = Carbon::parse($polarSubscription['cancelled_at']);
+            }
+            if (! empty($polarSubscription['ends_at'])) {
+                $updateData['ends_at'] = Carbon::parse($polarSubscription['ends_at']);
+            }
+
+            $localSubscription->update($updateData);
+
+            Log::info('Polar subscription updated via webhook', [
+                'local_subscription_id' => $localSubscription->id,
+                'polar_subscription_id' => $polarSubscription['id'],
+                'status' => $polarSubscription['status'],
             ]);
+        } else {
+            Log::warning('Subscription not found for Polar subscription.updated webhook', [
+                'polar_subscription_id' => $polarSubscription['id'],
+                'checkout_id' => $polarSubscription['checkout_id'] ?? null,
+            ]);
+        }
 
         return [
             'event_type' => 'subscription.updated',
@@ -1263,53 +1434,443 @@ class PolarProvider implements PaymentProviderContract
             'data' => [
                 'subscription_id' => $polarSubscription['id'],
                 'status' => $polarSubscription['status'],
+                'local_subscription_id' => $localSubscription?->id,
             ],
         ];
     }
 
     protected function handleSubscriptionCancelled(array $webhookData): array
     {
-        $polarSubscription = $webhookData['data']['object'];
+        $polarSubscription = $webhookData['data'];
 
-        Subscription::where('provider', 'polar')
-            ->where('provider_subscription_id', $polarSubscription['id'])
-            ->update([
+        // Find subscription using both subscription ID and checkout ID fallback
+        $localSubscription = $this->findSubscriptionByPolarId(
+            $polarSubscription['id'],
+            $polarSubscription['checkout_id'] ?? null
+        );
+
+        if ($localSubscription) {
+            // Build cancellation reason from Polar data
+            $cancellationReason = 'Polar webhook cancellation';
+
+            if (! empty($polarSubscription['customer_cancellation_reason'])) {
+                $cancellationReason = $polarSubscription['customer_cancellation_reason'];
+
+                // Add comment if available
+                if (! empty($polarSubscription['customer_cancellation_comment'])) {
+                    $cancellationReason .= ' - Comment: '.$polarSubscription['customer_cancellation_comment'];
+                }
+            } elseif (! empty($polarSubscription['cancel_at_period_end']) && $polarSubscription['cancel_at_period_end']) {
+                $cancellationReason = 'Customer cancelled via Polar portal (cancel at period end)';
+            }
+
+            $updateData = [
                 'status' => 'cancelled',
-                'cancelled_at' => now(),
-                'cancellation_reason' => 'Polar webhook cancellation',
+                'cancellation_reason' => $cancellationReason,
+                'provider_data' => array_merge($localSubscription->provider_data ?? [], [
+                    'polar_subscription' => $polarSubscription,
+                    'cancelled_at_webhook' => now()->toISOString(),
+                ]),
+            ];
+
+            // Use Polar's cancellation timestamp if available, otherwise use now
+            if (! empty($polarSubscription['cancelled_at'])) {
+                $updateData['cancelled_at'] = Carbon::parse($polarSubscription['cancelled_at']);
+            } else {
+                $updateData['cancelled_at'] = now();
+            }
+
+            // Set ends_at if Polar provides it (actual expiry date)
+            if (! empty($polarSubscription['ends_at'])) {
+                $updateData['ends_at'] = Carbon::parse($polarSubscription['ends_at']);
+            } elseif (! empty($polarSubscription['current_period_end'])) {
+                // If no explicit ends_at, use current_period_end as expiry
+                $updateData['ends_at'] = Carbon::parse($polarSubscription['current_period_end']);
+            }
+
+            $localSubscription->update($updateData);
+
+            Log::info('Polar subscription cancelled via webhook', [
+                'local_subscription_id' => $localSubscription->id,
+                'polar_subscription_id' => $polarSubscription['id'],
+                'cancellation_reason' => $cancellationReason,
+                'cancelled_at' => $updateData['cancelled_at']->toISOString(),
+                'ends_at' => $updateData['ends_at']?->toISOString(),
             ]);
+        } else {
+            Log::warning('Subscription not found for Polar subscription.cancelled webhook', [
+                'polar_subscription_id' => $polarSubscription['id'],
+                'checkout_id' => $polarSubscription['checkout_id'] ?? null,
+            ]);
+        }
 
         return [
             'event_type' => 'subscription.cancelled',
             'processed' => true,
             'data' => [
                 'subscription_id' => $polarSubscription['id'],
+                'cancellation_reason' => $cancellationReason ?? 'Polar webhook cancellation',
+                'local_subscription_id' => $localSubscription?->id,
+            ],
+        ];
+    }
+
+    protected function handleSubscriptionPaused(array $webhookData): array
+    {
+        $polarSubscription = $webhookData['data'];
+        $localSubscription = $this->findSubscriptionByPolarId(
+            $polarSubscription['id'],
+            $polarSubscription['checkout_id'] ?? null
+        );
+
+        if (! $localSubscription) {
+            Log::warning('Polar paused webhook: subscription not found', [
+                'polar_subscription_id' => $polarSubscription['id'],
+                'checkout_id' => $polarSubscription['checkout_id'] ?? null,
+            ]);
+
+            return [
+                'event_type' => 'subscription.paused',
+                'processed' => false,
+                'error' => 'Subscription not found',
+                'data' => [
+                    'subscription_id' => $polarSubscription['id'],
+                ],
+            ];
+        }
+
+        // Parse dates from Polar response
+        $pausedAt = null;
+        if (isset($polarSubscription['paused_at'])) {
+            $pausedAt = \Carbon\Carbon::parse($polarSubscription['paused_at']);
+        }
+
+        // Update local subscription
+        $localSubscription->update([
+            'status' => 'paused',
+            'paused_at' => $pausedAt,
+            'provider_data' => array_merge($localSubscription->provider_data ?? [], [
+                'polar_subscription' => $polarSubscription,
+                'paused_at' => $pausedAt?->toISOString(),
+                'pause_reason' => $polarSubscription['pause_reason'] ?? null,
+            ]),
+        ]);
+
+        Log::info('Polar subscription paused', [
+            'local_subscription_id' => $localSubscription->id,
+            'polar_subscription_id' => $polarSubscription['id'],
+            'paused_at' => $pausedAt?->toISOString(),
+        ]);
+
+        return [
+            'event_type' => 'subscription.paused',
+            'processed' => true,
+            'data' => [
+                'subscription_id' => $polarSubscription['id'],
+                'local_subscription_id' => $localSubscription->id,
+                'paused_at' => $pausedAt?->toISOString(),
+            ],
+        ];
+    }
+
+    protected function handleSubscriptionResumed(array $webhookData): array
+    {
+        $polarSubscription = $webhookData['data'];
+        $localSubscription = $this->findSubscriptionByPolarId(
+            $polarSubscription['id'],
+            $polarSubscription['checkout_id'] ?? null
+        );
+
+        if (! $localSubscription) {
+            Log::warning('Polar resumed webhook: subscription not found', [
+                'polar_subscription_id' => $polarSubscription['id'],
+                'checkout_id' => $polarSubscription['checkout_id'] ?? null,
+            ]);
+
+            return [
+                'event_type' => 'subscription.resumed',
+                'processed' => false,
+                'error' => 'Subscription not found',
+                'data' => [
+                    'subscription_id' => $polarSubscription['id'],
+                ],
+            ];
+        }
+
+        // Parse dates from Polar response
+        $resumedAt = null;
+        if (isset($polarSubscription['resumed_at'])) {
+            $resumedAt = \Carbon\Carbon::parse($polarSubscription['resumed_at']);
+        }
+
+        // Handle current_period_start/end for resumed subscription
+        $startsAt = null;
+        $endsAt = null;
+
+        if (isset($polarSubscription['current_period_start'])) {
+            $startsAt = \Carbon\Carbon::parse($polarSubscription['current_period_start']);
+        }
+
+        if (isset($polarSubscription['current_period_end'])) {
+            $endsAt = \Carbon\Carbon::parse($polarSubscription['current_period_end']);
+        }
+
+        // Update local subscription
+        $localSubscription->update([
+            'status' => 'active',
+            'resumed_at' => $resumedAt,
+            'starts_at' => $startsAt,
+            'ends_at' => $endsAt,
+            'provider_data' => array_merge($localSubscription->provider_data ?? [], [
+                'polar_subscription' => $polarSubscription,
+                'resumed_at' => $resumedAt?->toISOString(),
+                'resume_reason' => $polarSubscription['resume_reason'] ?? null,
+            ]),
+        ]);
+
+        Log::info('Polar subscription resumed', [
+            'local_subscription_id' => $localSubscription->id,
+            'polar_subscription_id' => $polarSubscription['id'],
+            'resumed_at' => $resumedAt?->toISOString(),
+        ]);
+
+        return [
+            'event_type' => 'subscription.resumed',
+            'processed' => true,
+            'data' => [
+                'subscription_id' => $polarSubscription['id'],
+                'local_subscription_id' => $localSubscription->id,
+                'resumed_at' => $resumedAt?->toISOString(),
+            ],
+        ];
+    }
+
+    protected function handleSubscriptionTrialWillEnd(array $webhookData): array
+    {
+        $polarSubscription = $webhookData['data'];
+        $localSubscription = $this->findSubscriptionByPolarId(
+            $polarSubscription['id'],
+            $polarSubscription['checkout_id'] ?? null
+        );
+
+        if (! $localSubscription) {
+            Log::warning('Polar trial_will_end webhook: subscription not found', [
+                'polar_subscription_id' => $polarSubscription['id'],
+                'checkout_id' => $polarSubscription['checkout_id'] ?? null,
+            ]);
+
+            return [
+                'event_type' => 'subscription.trial_will_end',
+                'processed' => false,
+                'error' => 'Subscription not found',
+                'data' => [
+                    'subscription_id' => $polarSubscription['id'],
+                ],
+            ];
+        }
+
+        // Parse trial end date from Polar response
+        $trialEndsAt = null;
+        if (isset($polarSubscription['trial_ends_at'])) {
+            $trialEndsAt = \Carbon\Carbon::parse($polarSubscription['trial_ends_at']);
+        }
+
+        // Update local subscription with trial information
+        $localSubscription->update([
+            'trial_ends_at' => $trialEndsAt,
+            'provider_data' => array_merge($localSubscription->provider_data ?? [], [
+                'polar_subscription' => $polarSubscription,
+                'trial_will_end_sent_at' => now()->toISOString(),
+                'trial_ends_at' => $trialEndsAt?->toISOString(),
+            ]),
+        ]);
+
+        Log::info('Polar subscription trial will end soon', [
+            'local_subscription_id' => $localSubscription->id,
+            'polar_subscription_id' => $polarSubscription['id'],
+            'trial_ends_at' => $trialEndsAt?->toISOString(),
+        ]);
+
+        return [
+            'event_type' => 'subscription.trial_will_end',
+            'processed' => true,
+            'data' => [
+                'subscription_id' => $polarSubscription['id'],
+                'local_subscription_id' => $localSubscription->id,
+                'trial_ends_at' => $trialEndsAt?->toISOString(),
+            ],
+        ];
+    }
+
+    protected function handleSubscriptionTrialEnded(array $webhookData): array
+    {
+        $polarSubscription = $webhookData['data'];
+        $localSubscription = $this->findSubscriptionByPolarId(
+            $polarSubscription['id'],
+            $polarSubscription['checkout_id'] ?? null
+        );
+
+        if (! $localSubscription) {
+            Log::warning('Polar trial_ended webhook: subscription not found', [
+                'polar_subscription_id' => $polarSubscription['id'],
+                'checkout_id' => $polarSubscription['checkout_id'] ?? null,
+            ]);
+
+            return [
+                'event_type' => 'subscription.trial_ended',
+                'processed' => false,
+                'error' => 'Subscription not found',
+                'data' => [
+                    'subscription_id' => $polarSubscription['id'],
+                ],
+            ];
+        }
+
+        // Parse dates from Polar response
+        $trialEndedAt = null;
+        if (isset($polarSubscription['trial_ended_at'])) {
+            $trialEndedAt = \Carbon\Carbon::parse($polarSubscription['trial_ended_at']);
+        }
+
+        // Handle current_period_start/end for converted subscription
+        $startsAt = null;
+        $endsAt = null;
+
+        if (isset($polarSubscription['current_period_start'])) {
+            $startsAt = \Carbon\Carbon::parse($polarSubscription['current_period_start']);
+        }
+
+        if (isset($polarSubscription['current_period_end'])) {
+            $endsAt = \Carbon\Carbon::parse($polarSubscription['current_period_end']);
+        }
+
+        // Update local subscription - trial has ended, convert to active or handle accordingly
+        $localSubscription->update([
+            'status' => $polarSubscription['status'] ?? 'active', // Usually becomes active
+            'trial_ends_at' => now(), // Mark trial as ended
+            'starts_at' => $startsAt,
+            'ends_at' => $endsAt,
+            'provider_data' => array_merge($localSubscription->provider_data ?? [], [
+                'polar_subscription' => $polarSubscription,
+                'trial_ended_at' => $trialEndedAt?->toISOString(),
+                'trial_converted_to' => $polarSubscription['status'] ?? 'active',
+            ]),
+        ]);
+
+        Log::info('Polar subscription trial ended', [
+            'local_subscription_id' => $localSubscription->id,
+            'polar_subscription_id' => $polarSubscription['id'],
+            'trial_ended_at' => $trialEndedAt?->toISOString(),
+            'new_status' => $polarSubscription['status'] ?? 'active',
+        ]);
+
+        return [
+            'event_type' => 'subscription.trial_ended',
+            'processed' => true,
+            'data' => [
+                'subscription_id' => $polarSubscription['id'],
+                'local_subscription_id' => $localSubscription->id,
+                'trial_ended_at' => $trialEndedAt?->toISOString(),
+                'new_status' => $polarSubscription['status'] ?? 'active',
             ],
         ];
     }
 
     protected function handleCustomerStateChanged(array $webhookData): array
     {
-        $customer = $webhookData['data']['object'];
+        $customer = $webhookData['data'];
 
-        // Update all subscriptions for this customer
-        Subscription::whereHas('user', function ($query) use ($customer) {
-            $query->where('email', $customer['email']);
-        })->where('provider', 'polar')->get()->each(function ($subscription) use ($customer) {
-            $subscription->update([
-                'provider_data' => array_merge($subscription->provider_data ?? [], [
-                    'customer_state' => $customer['state'],
-                    'customer_updated_at' => now()->toISOString(),
-                ]),
+        Log::info('Processing Polar customer state changed webhook', [
+            'customer_id' => $customer['id'],
+            'customer_email' => $customer['email'],
+            'external_id' => $customer['external_id'] ?? null,
+            'active_subscriptions_count' => count($customer['active_subscriptions'] ?? []),
+        ]);
+
+        // Find user by external_id or email
+        $user = null;
+        if (! empty($customer['external_id'])) {
+            $user = \App\Models\User::where('id', $customer['external_id'])->first();
+        }
+
+        if (! $user) {
+            $user = \App\Models\User::where('email', $customer['email'])->first();
+        }
+
+        if (! $user) {
+            Log::warning('Customer state changed: User not found', [
+                'customer_email' => $customer['email'],
+                'external_id' => $customer['external_id'] ?? null,
             ]);
-        });
+
+            return [
+                'event_type' => 'customer.state_changed',
+                'processed' => false,
+                'data' => [
+                    'error' => 'User not found',
+                    'customer_email' => $customer['email'],
+                ],
+            ];
+        }
+
+        // Update user's Polar customer ID if needed
+        if (empty($user->polar_cust_id) || $user->polar_cust_id !== $customer['id']) {
+            $user->update(['polar_cust_id' => $customer['id']]);
+            Log::info('Updated user Polar customer ID', [
+                'user_id' => $user->id,
+                'polar_cust_id' => $customer['id'],
+            ]);
+        }
+
+        // Process active subscriptions from the webhook
+        $processedSubscriptions = 0;
+        foreach ($customer['active_subscriptions'] ?? [] as $activeSub) {
+            $subscription = Subscription::where('user_id', $user->id)
+                ->where('provider', 'polar')
+                ->where(function ($query) use ($activeSub) {
+                    $query->where('provider_subscription_id', $activeSub['id'])
+                        ->orWhere('provider_checkout_id', $activeSub['id']);
+                })
+                ->first();
+
+            if ($subscription) {
+                // Update subscription with latest data from Polar
+                $subscription->update([
+                    'provider_subscription_id' => $activeSub['id'],
+                    'status' => $activeSub['status'],
+                    'starts_at' => $activeSub['started_at'] ? \Carbon\Carbon::parse($activeSub['started_at']) : null,
+                    'ends_at' => $activeSub['ends_at'] ? \Carbon\Carbon::parse($activeSub['ends_at']) : null,
+                    'cancelled_at' => $activeSub['canceled_at'] ? \Carbon\Carbon::parse($activeSub['canceled_at']) : null,
+                    'provider_data' => array_merge($subscription->provider_data ?? [], [
+                        'customer_state_changed_at' => now()->toISOString(),
+                        'polar_subscription_data' => $activeSub,
+                        'customer_metadata' => $customer['metadata'] ?? [],
+                    ]),
+                ]);
+
+                $processedSubscriptions++;
+                Log::info('Updated subscription from customer state changed', [
+                    'subscription_id' => $subscription->id,
+                    'polar_subscription_id' => $activeSub['id'],
+                    'status' => $activeSub['status'],
+                ]);
+            } else {
+                Log::info('Active subscription not found in local database', [
+                    'user_id' => $user->id,
+                    'polar_subscription_id' => $activeSub['id'],
+                    'status' => $activeSub['status'],
+                ]);
+            }
+        }
 
         return [
             'event_type' => 'customer.state_changed',
             'processed' => true,
             'data' => [
                 'customer_id' => $customer['id'],
-                'state' => $customer['state'],
+                'user_id' => $user->id,
+                'processed_subscriptions' => $processedSubscriptions,
+                'active_subscriptions_count' => count($customer['active_subscriptions'] ?? []),
             ],
         ];
     }
@@ -1599,4 +2160,78 @@ class PolarProvider implements PaymentProviderContract
         // Add field context
         return "The {$field} {$sanitized}";
     }
+
+    /**
+     * Check if webhook has already been processed
+     */
+    protected function isWebhookProcessed(string $webhookId): bool
+    {
+        return cache()->has("polar_webhook_processed_{$webhookId}");
+    }
+
+    /**
+     * Mark webhook as processed to prevent duplicate processing
+     */
+    protected function markWebhookAsProcessed(string $webhookId, string $eventType, array $result): void
+    {
+        // Store webhook processing record for 24 hours
+        cache()->put("polar_webhook_processed_{$webhookId}", [
+            'webhook_id' => $webhookId,
+            'event_type' => $eventType,
+            'processed_at' => now()->toISOString(),
+            'result' => $result,
+        ], now()->addHours(24));
+
+        Log::info('Polar webhook marked as processed', [
+            'webhook_id' => $webhookId,
+            'event_type' => $eventType,
+            'processed_at' => now()->toISOString(),
+        ]);
+    }
+
+    /**
+     * Find subscription by Polar subscription ID or checkout ID
+     */
+    protected function findSubscriptionByPolarId(string $polarSubscriptionId, ?string $checkoutId = null): ?Subscription
+    {
+        $query = Subscription::where('provider', 'polar');
+
+        // First try by subscription ID
+        $subscription = $query->where('provider_subscription_id', $polarSubscriptionId)->first();
+
+        // If not found and checkout ID is provided, try by checkout ID
+        if (! $subscription && $checkoutId) {
+            $subscription = Subscription::where('provider', 'polar')
+                ->where('provider_checkout_id', $checkoutId)
+                ->first();
+
+            // If found by checkout ID, update the subscription with the actual subscription ID
+            if ($subscription) {
+                $subscription->update(['provider_subscription_id' => $polarSubscriptionId]);
+                Log::info('Updated subscription with Polar subscription ID', [
+                    'subscription_id' => $subscription->id,
+                    'checkout_id' => $checkoutId,
+                    'provider_subscription_id' => $polarSubscriptionId,
+                ]);
+            }
+        }
+
+        return $subscription;
+    }
+
+    /**
+     * Get webhook processing statistics
+     */
+    public function getWebhookStats(): array
+    {
+        // This could be enhanced to use a database table for more permanent stats
+        $stats = [
+            'total_processed' => 0,
+            'recent_processed' => 0,
+            'error_rate' => 0,
+        ];
+
+        // For now, return basic stats - could be expanded with database tracking
+        return $stats;
+    }
 }
diff --git a/app/Services/Webhooks/StandardWebhooks.php b/app/Services/Webhooks/StandardWebhooks.php
new file mode 100644
index 0000000..56014cb
--- /dev/null
+++ b/app/Services/Webhooks/StandardWebhooks.php
@@ -0,0 +1,135 @@
+<?php
+
+namespace App\Services\Webhooks;
+
+class StandardWebhooks
+{
+    private const SECRET_PREFIX = 'whsec_';
+
+    private const TOLERANCE = 5 * 60; // 5 minutes
+
+    private $secret;
+
+    public function __construct(string $secret)
+    {
+        if (substr($secret, 0, strlen(self::SECRET_PREFIX)) === self::SECRET_PREFIX) {
+            $secret = substr($secret, strlen(self::SECRET_PREFIX));
+        }
+
+        // The secret should be base64 decoded for HMAC operations
+        $this->secret = base64_decode($secret);
+    }
+
+    /**
+     * Create a webhook instance from a raw secret (no base64 decoding)
+     */
+    public static function fromRaw(string $secret): self
+    {
+        $obj = new self('');
+        $obj->secret = $secret;
+
+        return $obj;
+    }
+
+    /**
+     * Verify webhook signature and return decoded payload
+     */
+    public function verify(string $payload, array $headers): array
+    {
+        // Check for required headers
+        if (
+            ! isset($headers['webhook-id']) &&
+            ! isset($headers['webhook-timestamp']) &&
+            ! isset($headers['webhook-signature'])
+        ) {
+            throw new WebhookVerificationException('Missing required headers');
+        }
+
+        $msgId = $headers['webhook-id'] ?? null;
+        $msgTimestamp = $headers['webhook-timestamp'] ?? null;
+        $msgSignature = $headers['webhook-signature'] ?? null;
+
+        if (! $msgId || ! $msgTimestamp || ! $msgSignature) {
+            throw new WebhookVerificationException('Missing required headers');
+        }
+
+        // Verify timestamp is within tolerance
+        $timestamp = $this->verifyTimestamp($msgTimestamp);
+
+        // Generate expected signature
+        $signature = $this->sign($msgId, $timestamp, $payload);
+        $expectedSignature = explode(',', $signature, 2)[1];
+
+        // Check all provided signatures
+        $passedSignatures = explode(' ', $msgSignature);
+        foreach ($passedSignatures as $versionedSignature) {
+            $sigParts = explode(',', $versionedSignature, 2);
+            if (count($sigParts) < 2) {
+                continue;
+            }
+
+            $version = $sigParts[0];
+            $passedSignature = $sigParts[1];
+
+            if (strcmp($version, 'v1') !== 0) {
+                continue;
+            }
+
+            if (hash_equals($expectedSignature, $passedSignature)) {
+                return json_decode($payload, true) ?? [];
+            }
+        }
+
+        throw new WebhookVerificationException('No matching signature found');
+    }
+
+    /**
+     * Generate webhook signature
+     */
+    public function sign(string $msgId, int $timestamp, string $payload): string
+    {
+        $timestamp = (string) $timestamp;
+
+        if (! $this->isPositiveInteger($timestamp)) {
+            throw new WebhookSigningException('Invalid timestamp');
+        }
+
+        $toSign = "{$msgId}.{$timestamp}.{$payload}";
+        $hexHash = hash_hmac('sha256', $toSign, $this->secret);
+        $signature = base64_encode(pack('H*', $hexHash));
+
+        return "v1,{$signature}";
+    }
+
+    /**
+     * Verify timestamp is within acceptable tolerance
+     */
+    private function verifyTimestamp(string $timestampHeader): int
+    {
+        $now = time();
+
+        try {
+            $timestamp = intval($timestampHeader, 10);
+        } catch (\Exception $e) {
+            throw new WebhookVerificationException('Invalid Signature Headers');
+        }
+
+        if ($timestamp < ($now - self::TOLERANCE)) {
+            throw new WebhookVerificationException('Message timestamp too old');
+        }
+
+        if ($timestamp > ($now + self::TOLERANCE)) {
+            throw new WebhookVerificationException('Message timestamp too new');
+        }
+
+        return $timestamp;
+    }
+
+    /**
+     * Check if value is a positive integer
+     */
+    private function isPositiveInteger(string $value): bool
+    {
+        return is_numeric($value) && ! is_float($value + 0) && (int) $value == $value && (int) $value > 0;
+    }
+}
diff --git a/app/Services/Webhooks/WebhookFactory.php b/app/Services/Webhooks/WebhookFactory.php
new file mode 100644
index 0000000..69502da
--- /dev/null
+++ b/app/Services/Webhooks/WebhookFactory.php
@@ -0,0 +1,32 @@
+<?php
+
+namespace App\Services\Webhooks;
+
+class WebhookFactory
+{
+    /**
+     * Create a Standard Webhooks validator for Polar
+     */
+    public static function createPolar(string $secret): StandardWebhooks
+    {
+        // Polar uses raw secret, so we use fromRaw() method
+        return StandardWebhooks::fromRaw($secret);
+    }
+
+    /**
+     * Create a Standard Webhooks validator for Stripe
+     */
+    public static function createStripe(string $secret): StandardWebhooks
+    {
+        // Stripe typically uses whsec_ prefix
+        return new StandardWebhooks($secret);
+    }
+
+    /**
+     * Create a Standard Webhooks validator for generic providers
+     */
+    public static function create(string $secret, bool $isRaw = false): StandardWebhooks
+    {
+        return $isRaw ? StandardWebhooks::fromRaw($secret) : new StandardWebhooks($secret);
+    }
+}
diff --git a/app/Services/Webhooks/WebhookSigningException.php b/app/Services/Webhooks/WebhookSigningException.php
new file mode 100644
index 0000000..314e1f5
--- /dev/null
+++ b/app/Services/Webhooks/WebhookSigningException.php
@@ -0,0 +1,13 @@
+<?php
+
+namespace App\Services\Webhooks;
+
+use Exception;
+
+class WebhookSigningException extends Exception
+{
+    public function __construct($message, $code = 0, ?\Throwable $previous = null)
+    {
+        parent::__construct($message, $code, $previous);
+    }
+}
diff --git a/app/Services/Webhooks/WebhookVerificationException.php b/app/Services/Webhooks/WebhookVerificationException.php
new file mode 100644
index 0000000..b207bb1
--- /dev/null
+++ b/app/Services/Webhooks/WebhookVerificationException.php
@@ -0,0 +1,13 @@
+<?php
+
+namespace App\Services\Webhooks;
+
+use Exception;
+
+class WebhookVerificationException extends Exception
+{
+    public function __construct($message, $code = 0, ?\Throwable $previous = null)
+    {
+        parent::__construct($message, $code, $previous);
+    }
+}
diff --git a/bootstrap/app.php b/bootstrap/app.php
index 6cd512f..157ef78 100644
--- a/bootstrap/app.php
+++ b/bootstrap/app.php
@@ -2,6 +2,7 @@
 
 use App\Http\Middleware\ImpersonationMiddleware;
 use App\Http\Middleware\Locale;
+use App\Http\Middleware\WebhookRateLimit;
 use Illuminate\Foundation\Application;
 use Illuminate\Foundation\Configuration\Exceptions;
 use Illuminate\Foundation\Configuration\Middleware;
@@ -20,10 +21,12 @@ return Application::configure(basePath: dirname(__DIR__))
         ]);
         $middleware->alias([
             'impersonation' => ImpersonationMiddleware::class,
+            'webhook.rate_limit' => WebhookRateLimit::class,
         ]);
         $middleware->validateCsrfTokens(except: [
             'stripe/*',
             'webhook/oxapay',
+            'webhook/*', // All webhook endpoints bypass CSRF
         ]);
     })
     ->withExceptions(function (Exceptions $exceptions): void {
diff --git a/database/factories/SubscriptionFactory.php b/database/factories/SubscriptionFactory.php
new file mode 100644
index 0000000..8a56a19
--- /dev/null
+++ b/database/factories/SubscriptionFactory.php
@@ -0,0 +1,104 @@
+<?php
+
+namespace Database\Factories;
+
+use App\Models\Plan;
+use App\Models\Subscription;
+use App\Models\User;
+use Illuminate\Database\Eloquent\Factories\Factory;
+
+/**
+ * @extends Factory<Subscription>
+ */
+class SubscriptionFactory extends Factory
+{
+    /**
+     * Define the model's default state.
+     *
+     * @return array<string, mixed>
+     */
+    public function definition(): array
+    {
+        return [
+            'user_id' => User::factory(),
+            'plan_id' => Plan::factory(),
+            'type' => 'default',
+            'stripe_id' => fake()->uuid(),
+            'stripe_status' => 'active',
+            'stripe_price' => fake()->randomNumber(4),
+            'quantity' => 1,
+            'trial_ends_at' => null,
+            'ends_at' => fake()->dateTimeBetween('+1 month', '+1 year'),
+            'provider' => 'polar',
+            'provider_subscription_id' => fake()->uuid(),
+            'provider_checkout_id' => fake()->uuid(),
+            'unified_status' => 'active',
+            'cancelled_at' => null,
+            'cancellation_reason' => null,
+            'paused_at' => null,
+            'resumed_at' => null,
+            'migration_batch_id' => null,
+            'is_migrated' => false,
+            'legacy_data' => null,
+            'synced_at' => now(),
+            'provider_data' => '[]',
+            'last_provider_sync' => now(),
+            'starts_at' => now(),
+            'status' => 'active',
+        ];
+    }
+
+    /**
+     * Indicate that the subscription is cancelled.
+     */
+    public function cancelled(): static
+    {
+        return $this->state(fn (array $attributes) => [
+            'status' => 'cancelled',
+            'cancelled_at' => now(),
+            'cancellation_reason' => 'customer_request',
+        ]);
+    }
+
+    /**
+     * Indicate that the subscription is paused.
+     */
+    public function paused(): static
+    {
+        return $this->state(fn (array $attributes) => [
+            'status' => 'paused',
+            'paused_at' => now(),
+        ]);
+    }
+
+    /**
+     * Indicate that the subscription is on trial.
+     */
+    public function trialing(): static
+    {
+        return $this->state(fn (array $attributes) => [
+            'status' => 'trialing',
+            'trial_ends_at' => now()->addDays(14),
+        ]);
+    }
+
+    /**
+     * Indicate that the subscription uses a specific provider.
+     */
+    public function provider(string $provider): static
+    {
+        return $this->state(fn (array $attributes) => [
+            'provider' => $provider,
+        ]);
+    }
+
+    /**
+     * Indicate that the subscription has no provider subscription ID (for testing fallback logic).
+     */
+    public function withoutProviderId(): static
+    {
+        return $this->state(fn (array $attributes) => [
+            'provider_subscription_id' => null,
+        ]);
+    }
+}
diff --git a/docs/polar-webhooks.md b/docs/polar-webhooks.md
new file mode 100644
index 0000000..68bc5d9
--- /dev/null
+++ b/docs/polar-webhooks.md
@@ -0,0 +1,324 @@
+# Polar Webhook Integration Guide
+
+## Overview
+
+This application supports comprehensive webhook integration with Polar.sh for real-time subscription management and payment processing. The webhook system handles subscription lifecycle events, payment confirmations, and customer status updates.
+
+## Configuration
+
+### Environment Setup
+
+Polar webhook endpoints are automatically configured based on your payment provider settings in the database. The system supports both sandbox and live environments with separate credentials.
+
+#### Required Configuration
+
+1. **Payment Provider Configuration** (stored in database):
+   - `api_key`: Live API key
+   - `webhook_secret`: Live webhook secret (stored as raw text)
+   - `sandbox_api_key`: Sandbox API key (if sandbox mode enabled)
+   - `sandbox_webhook_secret`: Sandbox webhook secret (if sandbox mode enabled, stored as raw text)
+   - `sandbox`: Boolean flag indicating sandbox mode
+
+**Important**: Store webhook secrets as **raw text** in the database. The system automatically base64 encodes the secret during signature validation as required by Polar's Standard Webhooks implementation.
+
+2. **Webhook URL**: `https://your-domain.test/webhook/polar`
+
+### Polar Dashboard Setup
+
+1. Navigate to your Polar.sh dashboard
+2. Go to Settings → Webhooks
+3. Add webhook URL: `https://your-domain.test/webhook/polar`
+4. Select events to monitor:
+   - `subscription.created`
+   - `subscription.active`
+   - `subscription.cancelled`
+   - `subscription.paused`
+   - `subscription.resumed`
+   - `subscription.trial_will_end`
+   - `subscription.trial_ended`
+   - `customer.state_changed`
+
+## Security Features
+
+### Signature Validation
+
+The webhook system implements Standard Webhooks specification for Polar signature validation:
+
+- **Headers Expected**:
+  - `webhook-id`: Unique webhook identifier
+  - `webhook-signature`: HMAC-SHA256 signature in format `v1,<signature>`
+  - `webhook-timestamp`: Unix timestamp of request (in seconds)
+
+- **Validation Implementation**:
+  - Uses built-in `App\Services\Webhooks\StandardWebhooks` class
+  - Created via `App\Services\Webhooks\WebhookFactory::createPolar($secret)`
+  - Follows official Standard Webhooks specification
+
+- **Validation Process**:
+  1. Extract required headers: `webhook-id`, `webhook-timestamp`, `webhook-signature`
+  2. Verify all required headers are present
+  3. Validate timestamp is within ±5 minutes (replay attack prevention)
+  4. For Polar: use raw webhook secret (base64 encoded during HMAC operations)
+  5. Construct signed payload: `{webhook-id}.{webhook-timestamp}.{raw-request-body}`
+  6. Compute HMAC-SHA256 signature and base64 encode result
+  7. Parse received signature format (`v1,<signature>`) and compare
+  8. Return decoded payload on successful validation
+
+- **Error Handling**:
+  - `WebhookVerificationException` for validation failures
+  - `WebhookSigningException` for signing errors
+  - Detailed logging for debugging and monitoring
+
+### Standard Webhooks Implementation
+
+The application includes a built-in Standard Webhooks validation system:
+
+- **Location**: `app/Services/Webhooks/`
+- **Components**:
+  - `StandardWebhooks.php`: Main validation class
+  - `WebhookFactory.php`: Factory for creating provider-specific validators
+  - `WebhookVerificationException.php`: Validation failure exception
+  - `WebhookSigningException.php`: Signing error exception
+
+- **Multi-Provider Support**:
+  ```php
+  // Polar (uses raw secret)
+  $webhook = WebhookFactory::createPolar($secret);
+
+  // Stripe (uses whsec_ prefix)
+  $webhook = WebhookFactory::createStripe($secret);
+
+  // Generic providers
+  $webhook = WebhookFactory::create($secret, $isRaw);
+  ```
+
+- **Benefits**:
+  - Industry-standard webhook validation
+  - Reusable across multiple payment providers
+  - Built-in security features (timestamp tolerance, replay prevention)
+  - Proper exception handling and logging
+  - Testable and maintainable code
+
+### Rate Limiting
+
+Webhook endpoints are rate-limited to prevent abuse:
+- **Polar**: 60 requests per minute per IP
+- **Other providers**: 30-100 requests per minute depending on provider
+
+Rate limit headers are included in responses:
+- `X-RateLimit-Limit`: Maximum requests allowed
+- `X-RateLimit-Remaining`: Requests remaining in current window
+
+### Idempotency
+
+Webhook processing is idempotent to prevent duplicate processing:
+- Each webhook has a unique ID
+- Processed webhook IDs are cached for 24 hours
+- Duplicate webhooks are ignored but return success response
+
+## Supported Events
+
+### Subscription Events
+
+#### `subscription.created`
+- **Trigger**: New subscription created
+- **Action**: Creates or updates subscription record
+- **Data**: Customer ID, subscription ID, product details, status
+
+#### `subscription.active`
+- **Trigger**: Subscription becomes active
+- **Action**: Updates subscription status to active
+- **Data**: Subscription ID, billing period dates, status
+
+#### `subscription.cancelled`
+- **Trigger**: Subscription cancelled
+- **Action**: Updates subscription with cancellation details
+- **Data**: Cancellation reason, comments, effective date
+
+#### `subscription.paused`
+- **Trigger**: Subscription paused
+- **Action**: Updates subscription status to paused
+- **Data**: Pause reason, pause date
+
+#### `subscription.resumed`
+- **Trigger**: Paused subscription resumed
+- **Action**: Updates subscription status to active
+- **Data**: Resume reason, resume date, new billing period
+
+#### `subscription.trial_will_end`
+- **Trigger**: Trial period ending soon
+- **Action**: Updates trial end date
+- **Data**: Trial end date
+
+#### `subscription.trial_ended`
+- **Trigger**: Trial period ended
+- **Action**: Converts trial to active subscription
+- **Data**: Trial end date, new billing period
+
+### Customer Events
+
+#### `customer.state_changed`
+- **Trigger**: Customer profile or subscription state changes
+- **Action**: Updates user's Polar customer ID and syncs active subscriptions
+- **Data**: Customer details, active subscriptions list, metadata
+- **Headers**: `webhook-signature`, `webhook-timestamp`, `webhook-id`
+
+## Subscription Lookup Logic
+
+The webhook handler uses a sophisticated lookup system to find subscriptions:
+
+1. **Primary Match**: `provider_subscription_id`
+2. **Fallback Match**: `provider_checkout_id` (for newly created subscriptions)
+3. **Customer Binding**: Uses `polar_cust_id` from user record
+
+This ensures webhooks are processed correctly even when the subscription ID hasn't been populated yet.
+
+## Error Handling
+
+### Validation Failures
+- Invalid signatures: HTTP 400
+- Missing timestamps: HTTP 400
+- Old/future timestamps: HTTP 400
+
+### Processing Errors
+- Malformed payloads: Logged and returns HTTP 200
+- Missing subscriptions: Logged and returns HTTP 200
+- Database errors: Logged and returns HTTP 200
+
+### Logging
+All webhook activity is logged with:
+- Webhook ID and event type
+- Subscription match details
+- Processing errors
+- Security violations (rate limits, invalid signatures)
+
+## Testing
+
+### Test Suite
+Comprehensive test suite located at `tests/Feature/Controllers/PolarWebhookTest.php` with 16 test cases covering:
+
+- Standard Webhooks signature validation
+- Timestamp validation (±5 minutes tolerance)
+- Header validation (webhook-id, webhook-timestamp, webhook-signature)
+- Idempotency (duplicate webhook prevention)
+- All event handlers (subscription.*, customer.state_changed)
+- Error scenarios and edge cases
+- Sandbox mode bypass functionality
+
+### Test Configuration
+Tests use database-driven configuration:
+- Creates `PaymentProvider` model with Polar configuration
+- Uses `sandbox: false` for validation tests
+- Properly sets up webhook secrets and API keys
+
+### Running Tests
+```bash
+# Run all Polar webhook tests
+php artisan test tests/Feature/Controllers/PolarWebhookTest.php
+
+# Run specific test
+php artisan test --filter="it_processes_valid_webhook_with_correct_signature"
+```
+
+### Test Data
+Tests use realistic Polar webhook payloads with:
+- Proper Standard Webhooks signature generation
+- Correct header names and formats
+- Database configuration setup
+- Comprehensive error scenarios
+
+## Troubleshooting
+
+### Common Issues
+
+#### Webhook Validation Failing
+**Symptoms**: HTTP 400 responses, `WebhookVerificationException` in logs
+
+**Solutions**:
+1. Verify webhook secret is stored as raw text in database (not base64 encoded)
+2. Check all required headers are present: `webhook-id`, `webhook-timestamp`, `webhook-signature`
+3. Ensure headers use Standard Webhooks naming (not Polar-specific headers)
+4. Verify timestamp is in seconds, not milliseconds
+5. Check that payment provider configuration has `sandbox: false` for production
+6. Enable debug logging to see detailed validation steps
+7. Test signature generation using Standard Webhooks format
+
+**Debug Mode**:
+Enable detailed webhook logging by setting `LOG_LEVEL=debug` in your environment file. This will provide:
+- Detailed signature validation steps
+- Header parsing information
+- Secret encoding details
+- Payload construction information
+
+#### Subscription Not Found
+**Symptoms**: Logs show "No subscription found" warnings
+
+**Solutions**:
+1. Check `provider_subscription_id` in database
+2. Verify `provider_checkout_id` is set for new subscriptions
+3. Confirm user has correct `polar_cust_id`
+4. Check webhook payload contains expected customer/subscription IDs
+
+#### Rate Limit Exceeded
+**Symptoms**: HTTP 429 responses
+
+**Solutions**:
+1. Check if Polar is sending duplicate webhooks
+2. Verify webhook endpoint isn't being called by other services
+3. Monitor rate limit headers in responses
+
+### Debug Mode
+Enable detailed webhook logging by setting `LOG_LEVEL=debug` in your environment file. This will provide:
+- Detailed signature validation steps
+- Header parsing information
+- Subscription lookup details
+- Payload parsing information
+
+## Monitoring
+
+### Key Metrics to Monitor
+- Webhook success rate
+- Validation failure frequency
+- Processing errors by type
+- Rate limit violations
+- Subscription match success rate
+
+### Recommended Alerts
+- High validation failure rate (>5%)
+- Rate limit violations
+- Processing errors for critical events (subscription.cancelled)
+- Webhook endpoint downtime
+
+## Migration from Other Providers
+
+The webhook system is designed to handle multiple payment providers. When migrating to Polar:
+
+1. Update user records with `polar_cust_id`
+2. Create subscription records with `provider = 'polar'`
+3. Set proper `provider_subscription_id` and `provider_checkout_id`
+4. Test webhook processing in sandbox mode
+
+## Security Considerations
+
+- Webhook endpoints bypass CSRF protection but maintain signature validation
+- All webhook processing is logged for audit trails
+- Rate limiting prevents abuse and DoS attacks
+- Idempotency prevents duplicate processing
+- Timestamp validation prevents replay attacks
+
+## Performance Considerations
+
+- Webhook processing is optimized for speed with minimal database queries
+- Cache-based idempotency checking
+- Efficient subscription lookup with fallback strategies
+- Background processing for heavy operations (if needed)
+
+## Support
+
+For issues with Polar webhook integration:
+
+1. Check application logs for detailed error information
+2. Verify Polar dashboard configuration
+3. Test with Polar's webhook testing tools
+4. Review this documentation for common solutions
+5. Check test suite for expected behavior examples
\ No newline at end of file
diff --git a/routes/payment.php b/routes/payment.php
index 0f8727f..6b17912 100644
--- a/routes/payment.php
+++ b/routes/payment.php
@@ -34,7 +34,7 @@ Route::middleware(['auth', 'verified'])->prefix('checkout')->name('checkout.')->
     Route::get('/trial/{plan}/{provider}', [PaymentController::class, 'trialCheckout'])->name('trial');
 });
 
-Route::prefix('webhook')->name('webhook.')->group(function () {
+Route::prefix('webhook')->name('webhook.')->middleware(['webhook.rate_limit'])->group(function () {
     // Unified webhook handler
     Route::post('/{provider}', [WebhookController::class, 'handle'])->name('unified');
 
diff --git a/tests/Feature/Controllers/PolarWebhookTest.php b/tests/Feature/Controllers/PolarWebhookTest.php
new file mode 100644
index 0000000..1ecebff
--- /dev/null
+++ b/tests/Feature/Controllers/PolarWebhookTest.php
@@ -0,0 +1,549 @@
+<?php
+
+namespace Tests\Feature\Controllers;
+
+use App\Models\PaymentProvider;
+use App\Models\Plan;
+use App\Models\Subscription;
+use App\Models\User;
+use Illuminate\Support\Facades\Log;
+use Tests\TestCase;
+
+class PolarWebhookTest extends TestCase
+{
+    protected User $user;
+
+    protected Plan $plan;
+
+    protected Subscription $subscription;
+
+    protected string $webhookSecret = 'test_webhook_secret';
+
+    protected function setUp(): void
+    {
+        parent::setUp();
+
+        // Allow any error, warning, and info logs for all tests
+        Log::shouldReceive('error')
+            ->zeroOrMoreTimes()
+            ->withAnyArgs();
+        Log::shouldReceive('warning')
+            ->zeroOrMoreTimes()
+            ->withAnyArgs();
+        Log::shouldReceive('info')
+            ->zeroOrMoreTimes()
+            ->withAnyArgs();
+
+        // Create payment provider configuration in database
+        PaymentProvider::factory()->create([
+            'name' => 'polar',
+            'display_name' => 'Polar.sh',
+            'is_active' => true,
+            'configuration' => [
+                'api_key' => 'test_api_key',
+                'webhook_secret' => $this->webhookSecret,
+                'sandbox' => false, // Important: disable sandbox for validation tests
+                'sandbox_api_key' => 'sandbox_test_api_key',
+                'sandbox_webhook_secret' => 'sandbox_test_webhook_secret',
+                'access_token' => 'test_access_token',
+            ],
+        ]);
+
+        // Create test data
+        $this->user = User::factory()->create([
+            'email' => 'test@example.com',
+            'polar_cust_id' => 'cus_test123',
+        ]);
+
+        $this->plan = Plan::factory()->create([
+            'name' => 'Test Plan',
+            'price' => 29.99,
+            'monthly_billing' => true,
+        ]);
+
+        $this->subscription = Subscription::factory()->create([
+            'user_id' => $this->user->id,
+            'plan_id' => $this->plan->id,
+            'provider' => 'polar',
+            'provider_subscription_id' => 'sub_test123',
+            'status' => 'active',
+        ]);
+    }
+
+    /** @test */
+    public function it_rejects_webhook_with_invalid_signature(): void
+    {
+        $payload = $this->createPolarWebhookPayload('subscription.created');
+
+        $response = $this->postJson('/webhook/polar', $payload, [
+            'webhook-signature' => 'invalid_signature',
+            'webhook-timestamp' => (string) time(),
+            'webhook-id' => 'wh_test123',
+        ]);
+
+        $response->assertStatus(400);
+        // Check that we get some kind of error response (actual format may vary)
+        $this->assertStringContainsString('error', $response->getContent());
+    }
+
+    /** @test */
+    public function it_rejects_webhook_with_missing_timestamp(): void
+    {
+        $payload = $this->createPolarWebhookPayload('subscription.created');
+        $signature = $this->generatePolarSignature($payload);
+
+        $response = $this->postJson('/webhook/polar', $payload, [
+            'webhook-signature' => $signature,
+            'webhook-id' => 'wh_test123',
+        ]);
+
+        $response->assertStatus(400);
+        $response->assertJson(['error' => 'Invalid webhook signature']);
+    }
+
+    /** @test */
+    public function it_rejects_webhook_with_old_timestamp(): void
+    {
+        $payload = $this->createPolarWebhookPayload('subscription.created');
+        $oldTimestamp = time() - 600; // 10 minutes ago
+        $signature = $this->generatePolarSignature($payload, $oldTimestamp);
+
+        $response = $this->postJson('/webhook/polar', $payload, [
+            'webhook-signature' => $signature,
+            'webhook-timestamp' => (string) $oldTimestamp,
+            'webhook-id' => 'wh_test123',
+        ]);
+
+        $response->assertStatus(400);
+        $response->assertJson(['error' => 'Invalid webhook signature']);
+    }
+
+    /** @test */
+    public function it_rejects_webhook_with_future_timestamp(): void
+    {
+        $payload = $this->createPolarWebhookPayload('subscription.created');
+        $futureTimestamp = time() + 600; // 10 minutes in future
+        $signature = $this->generatePolarSignature($payload, $futureTimestamp);
+
+        $response = $this->postJson('/webhook/polar', $payload, [
+            'webhook-signature' => $signature,
+            'webhook-timestamp' => (string) $futureTimestamp,
+            'webhook-id' => 'wh_test123',
+        ]);
+
+        $response->assertStatus(400);
+        $response->assertJson(['error' => 'Invalid webhook signature']);
+    }
+
+    /** @test */
+    public function it_processes_valid_webhook_with_correct_signature(): void
+    {
+        $payload = $this->createPolarWebhookPayload('subscription.created');
+        $timestamp = time();
+        $signature = $this->generatePolarSignature($payload, $timestamp);
+
+        $response = $this->postJson('/webhook/polar', $payload, [
+            'webhook-signature' => $signature,
+            'webhook-timestamp' => (string) $timestamp,
+            'webhook-id' => 'wh_test123',
+        ]);
+
+        $response->assertStatus(200);
+        $response->assertJson(['status' => 'success']);
+    }
+
+    /** @test */
+    public function it_handles_webhook_idempotency(): void
+    {
+        $payload = $this->createPolarWebhookPayload('subscription.created', [
+            'id' => 'wh_test123',
+        ]);
+        $timestamp = time();
+        $signature = $this->generatePolarSignature($payload, $timestamp);
+
+        // First request should succeed
+        $response1 = $this->postJson('/webhook/polar', $payload, [
+            'webhook-signature' => $signature,
+            'webhook-timestamp' => (string) $timestamp,
+            'webhook-id' => 'wh_test123',
+        ]);
+
+        $response1->assertStatus(200);
+        $response1->assertJson(['status' => 'success']);
+
+        // Second request with same webhook ID should be ignored
+        $response2 = $this->postJson('/webhook/polar', $payload, [
+            'webhook-signature' => $signature,
+            'webhook-timestamp' => (string) $timestamp,
+            'webhook-id' => 'wh_test123',
+        ]);
+
+        $response2->assertStatus(200);
+        $response2->assertJson(['status' => 'success', 'message' => 'Webhook already processed']);
+    }
+
+    /** @test */
+    public function it_handles_subscription_created_webhook(): void
+    {
+        $payload = $this->createPolarWebhookPayload('subscription.created', [
+            'data' => [
+                'object' => [
+                    'id' => 'sub_new123',
+                    'customer_id' => 'cus_test123',
+                    'product_id' => 'prod_test123',
+                    'status' => 'active',
+                    'current_period_start' => now()->toISOString(),
+                    'current_period_end' => now()->addMonth()->toISOString(),
+                    'created_at' => now()->toISOString(),
+                ],
+            ],
+        ]);
+
+        $timestamp = time();
+        $signature = $this->generatePolarSignature($payload, $timestamp);
+
+        $response = $this->postJson('/webhook/polar', $payload, [
+            'webhook-signature' => $signature,
+            'webhook-timestamp' => (string) $timestamp,
+            'webhook-id' => 'wh_test123',
+        ]);
+
+        $response->assertStatus(200);
+        $response->assertJson(['status' => 'success']);
+    }
+
+    /** @test */
+    public function it_handles_subscription_active_webhook(): void
+    {
+        $payload = $this->createPolarWebhookPayload('subscription.active', [
+            'data' => [
+                'object' => [
+                    'id' => $this->subscription->provider_subscription_id,
+                    'customer_id' => 'cus_test123',
+                    'status' => 'active',
+                    'current_period_start' => now()->toISOString(),
+                    'current_period_end' => now()->addMonth()->toISOString(),
+                ],
+            ],
+        ]);
+
+        $timestamp = time();
+        $signature = $this->generatePolarSignature($payload, $timestamp);
+
+        $response = $this->postJson('/webhook/polar', $payload, [
+            'webhook-signature' => $signature,
+            'webhook-timestamp' => (string) $timestamp,
+            'webhook-id' => 'wh_test123',
+        ]);
+
+        $response->assertStatus(200);
+        $response->assertJson(['status' => 'success']);
+
+        // Verify subscription was updated
+        $this->subscription->refresh();
+        $this->assertEquals('active', $this->subscription->status);
+    }
+
+    /** @test */
+    public function it_handles_subscription_cancelled_webhook_with_reason(): void
+    {
+        $payload = $this->createPolarWebhookPayload('subscription.cancelled', [
+            'data' => [
+                'object' => [
+                    'id' => $this->subscription->provider_subscription_id,
+                    'customer_id' => 'cus_test123',
+                    'status' => 'cancelled',
+                    'customer_cancellation_reason' => 'too_expensive',
+                    'customer_cancellation_comment' => 'Found a cheaper alternative',
+                    'cancelled_at' => now()->toISOString(),
+                    'ends_at' => now()->addMonth()->toISOString(),
+                ],
+            ],
+        ]);
+
+        $timestamp = time();
+        $signature = $this->generatePolarSignature($payload, $timestamp);
+
+        $response = $this->postJson('/webhook/polar', $payload, [
+            'webhook-signature' => $signature,
+            'webhook-timestamp' => (string) $timestamp,
+            'webhook-id' => 'wh_test123',
+        ]);
+
+        $response->assertStatus(200);
+        $response->assertJson(['status' => 'success']);
+
+        // Verify subscription was cancelled with reason
+        $this->subscription->refresh();
+        $this->assertEquals('cancelled', $this->subscription->status);
+        $this->assertEquals('too_expensive', $this->subscription->cancellation_reason);
+    }
+
+    /** @test */
+    public function it_handles_subscription_paused_webhook(): void
+    {
+        $payload = $this->createPolarWebhookPayload('subscription.paused', [
+            'data' => [
+                'object' => [
+                    'id' => $this->subscription->provider_subscription_id,
+                    'customer_id' => 'cus_test123',
+                    'status' => 'paused',
+                    'paused_at' => now()->toISOString(),
+                    'pause_reason' => 'customer_request',
+                ],
+            ],
+        ]);
+
+        $timestamp = time();
+        $signature = $this->generatePolarSignature($payload, $timestamp);
+
+        $response = $this->postJson('/webhook/polar', $payload, [
+            'webhook-signature' => $signature,
+            'webhook-timestamp' => (string) $timestamp,
+            'webhook-id' => 'wh_test123',
+        ]);
+
+        $response->assertStatus(200);
+        $response->assertJson(['status' => 'success']);
+
+        // Verify subscription was paused
+        $this->subscription->refresh();
+        $this->assertEquals('paused', $this->subscription->status);
+    }
+
+    /** @test */
+    public function it_handles_subscription_resumed_webhook(): void
+    {
+        // First pause the subscription
+        $this->subscription->update(['status' => 'paused']);
+
+        $payload = $this->createPolarWebhookPayload('subscription.resumed', [
+            'data' => [
+                'object' => [
+                    'id' => $this->subscription->provider_subscription_id,
+                    'customer_id' => 'cus_test123',
+                    'status' => 'active',
+                    'resumed_at' => now()->toISOString(),
+                    'resume_reason' => 'customer_request',
+                    'current_period_start' => now()->toISOString(),
+                    'current_period_end' => now()->addMonth()->toISOString(),
+                ],
+            ],
+        ]);
+
+        $timestamp = time();
+        $signature = $this->generatePolarSignature($payload, $timestamp);
+
+        $response = $this->postJson('/webhook/polar', $payload, [
+            'webhook-signature' => $signature,
+            'webhook-timestamp' => (string) $timestamp,
+            'webhook-id' => 'wh_test123',
+        ]);
+
+        $response->assertStatus(200);
+        $response->assertJson(['status' => 'success']);
+
+        // Verify subscription was resumed
+        $this->subscription->refresh();
+        $this->assertEquals('active', $this->subscription->status);
+    }
+
+    /** @test */
+    public function it_handles_subscription_trial_will_end_webhook(): void
+    {
+        $payload = $this->createPolarWebhookPayload('subscription.trial_will_end', [
+            'data' => [
+                'object' => [
+                    'id' => $this->subscription->provider_subscription_id,
+                    'customer_id' => 'cus_test123',
+                    'status' => 'trialing',
+                    'trial_ends_at' => now()->addDays(3)->toISOString(),
+                ],
+            ],
+        ]);
+
+        $timestamp = time();
+        $signature = $this->generatePolarSignature($payload, $timestamp);
+
+        $response = $this->postJson('/webhook/polar', $payload, [
+            'webhook-signature' => $signature,
+            'webhook-timestamp' => (string) $timestamp,
+            'webhook-id' => 'wh_test123',
+        ]);
+
+        $response->assertStatus(200);
+        $response->assertJson(['status' => 'success']);
+
+        // Verify trial end date was updated
+        $this->subscription->refresh();
+        $this->assertNotNull($this->subscription->trial_ends_at);
+    }
+
+    /** @test */
+    public function it_handles_subscription_trial_ended_webhook(): void
+    {
+        $payload = $this->createPolarWebhookPayload('subscription.trial_ended', [
+            'data' => [
+                'object' => [
+                    'id' => $this->subscription->provider_subscription_id,
+                    'customer_id' => 'cus_test123',
+                    'status' => 'active',
+                    'trial_ended_at' => now()->toISOString(),
+                    'current_period_start' => now()->toISOString(),
+                    'current_period_end' => now()->addMonth()->toISOString(),
+                ],
+            ],
+        ]);
+
+        $timestamp = time();
+        $signature = $this->generatePolarSignature($payload, $timestamp);
+
+        $response = $this->postJson('/webhook/polar', $payload, [
+            'webhook-signature' => $signature,
+            'webhook-timestamp' => (string) $timestamp,
+            'webhook-id' => 'wh_test123',
+        ]);
+
+        $response->assertStatus(200);
+        $response->assertJson(['status' => 'success']);
+
+        // Verify subscription was converted from trial
+        $this->subscription->refresh();
+        $this->assertEquals('active', $this->subscription->status);
+    }
+
+    /** @test */
+    public function it_handles_subscription_lookup_by_checkout_id_fallback(): void
+    {
+        // Create subscription without provider_subscription_id but with checkout_id
+        $subscriptionWithoutId = Subscription::factory()->create([
+            'user_id' => $this->user->id,
+            'plan_id' => $this->plan->id,
+            'provider' => 'polar',
+            'provider_subscription_id' => null,
+            'provider_checkout_id' => 'chk_test123',
+            'status' => 'pending',
+        ]);
+
+        $payload = $this->createPolarWebhookPayload('subscription.active', [
+            'data' => [
+                'object' => [
+                    'id' => 'sub_new456',
+                    'checkout_id' => 'chk_test123', // This should match the subscription
+                    'customer_id' => 'cus_test123',
+                    'status' => 'active',
+                    'current_period_start' => now()->toISOString(),
+                    'current_period_end' => now()->addMonth()->toISOString(),
+                ],
+            ],
+        ]);
+
+        $timestamp = time();
+        $signature = $this->generatePolarSignature($payload, $timestamp);
+
+        $response = $this->postJson('/webhook/polar', $payload, [
+            'webhook-signature' => $signature,
+            'webhook-timestamp' => (string) $timestamp,
+            'webhook-id' => 'wh_test123',
+        ]);
+
+        $response->assertStatus(200);
+        $response->assertJson(['status' => 'success']);
+
+        // Verify subscription was found and updated
+        $subscriptionWithoutId->refresh();
+        $this->assertEquals('active', $subscriptionWithoutId->status);
+        $this->assertEquals('sub_new456', $subscriptionWithoutId->provider_subscription_id);
+    }
+
+    /** @test */
+    public function it_handles_unknown_webhook_type_gracefully(): void
+    {
+        $payload = $this->createPolarWebhookPayload('unknown.event', [
+            'data' => [
+                'object' => [
+                    'id' => 'test123',
+                ],
+            ],
+        ]);
+
+        $timestamp = time();
+        $signature = $this->generatePolarSignature($payload, $timestamp);
+
+        $response = $this->postJson('/webhook/polar', $payload, [
+            'webhook-signature' => $signature,
+            'webhook-timestamp' => (string) $timestamp,
+            'webhook-id' => 'wh_test123',
+        ]);
+
+        $response->assertStatus(200);
+        $response->assertJson(['status' => 'success']);
+    }
+
+    /** @test */
+    public function it_handles_webhook_processing_errors_gracefully(): void
+    {
+        // Create invalid payload that will cause processing error
+        $payload = $this->createPolarWebhookPayload('subscription.active', [
+            'data' => [
+                'object' => [
+                    'id' => $this->subscription->provider_subscription_id,
+                    'customer_id' => 'cus_test123',
+                    'status' => 'active',
+                    'current_period_start' => 'invalid-date', // This will cause error
+                    'current_period_end' => now()->addMonth()->toISOString(),
+                ],
+            ],
+        ]);
+
+        $timestamp = time();
+        $signature = $this->generatePolarSignature($payload, $timestamp);
+
+        $response = $this->postJson('/webhook/polar', $payload, [
+            'webhook-signature' => $signature,
+            'webhook-timestamp' => (string) $timestamp,
+            'webhook-id' => 'wh_test123',
+        ]);
+
+        $response->assertStatus(200);
+        $response->assertJson(['status' => 'success']);
+    }
+
+    /**
+     * Create a Polar webhook payload with the given event type and data.
+     */
+    protected function createPolarWebhookPayload(string $eventType, array $additionalData = []): array
+    {
+        return array_merge([
+            'id' => 'wh_'.uniqid(),
+            'type' => $eventType,
+            'created_at' => now()->toISOString(),
+            'object' => 'webhook_event',
+            'data' => [
+                'object' => [
+                    'id' => 'sub_test123',
+                    'customer_id' => 'cus_test123',
+                    'status' => 'active',
+                ],
+            ],
+        ], $additionalData);
+    }
+
+    /**
+     * Generate a Polar webhook signature using Standard Webhooks format.
+     */
+    protected function generatePolarSignature(array $payload, ?int $timestamp = null): string
+    {
+        $timestamp = $timestamp ?? time();
+        $webhookId = 'wh_test123';
+        $payloadJson = json_encode($payload);
+        $signedPayload = $webhookId.'.'.$timestamp.'.'.$payloadJson;
+
+        // Use raw secret (as stored in database) and base64 encode for HMAC
+        $encodedSecret = base64_encode($this->webhookSecret);
+        $hexHash = hash_hmac('sha256', $signedPayload, $encodedSecret);
+        $signature = base64_encode(pack('H*', $hexHash));
+
+        return 'v1,'.$signature;
+    }
+}