From 45c75ad9c16e860af5065010bfa0bea7106d8e88 Mon Sep 17 00:00:00 2001
From: Andras Bacsai <5845193+andrasbacsai@users.noreply.github.com>
Date: Sun, 7 Sep 2025 18:57:20 +0200
Subject: [PATCH] feat(ssh): add Sentry tracking for SSH retry events to
 enhance error monitoring

---
 app/Traits/ExecuteRemoteCommand.php |  8 ++++++
 app/Traits/SshRetryable.php         | 41 +++++++++++++++++++++++++++++
 2 files changed, 49 insertions(+)

diff --git a/app/Traits/ExecuteRemoteCommand.php b/app/Traits/ExecuteRemoteCommand.php
index 398f05bc9..0e7961368 100644
--- a/app/Traits/ExecuteRemoteCommand.php
+++ b/app/Traits/ExecuteRemoteCommand.php
@@ -62,6 +62,14 @@ trait ExecuteRemoteCommand
                     if ($this->isRetryableSshError($errorMessage) && $attempt < $maxRetries - 1) {
                         $attempt++;
                         $delay = $this->calculateRetryDelay($attempt - 1);
+
+                        // Track SSH retry event in Sentry
+                        $this->trackSshRetryEvent($attempt, $maxRetries, $delay, $errorMessage, [
+                            'server' => $this->server->name ?? $this->server->ip ?? 'unknown',
+                            'command' => remove_iip($command),
+                            'trait' => 'ExecuteRemoteCommand',
+                        ]);
+
                         // Add log entry for the retry
                         if (isset($this->application_deployment_queue)) {
                             $this->addRetryLogEntry($attempt, $maxRetries, $delay, $errorMessage);
diff --git a/app/Traits/SshRetryable.php b/app/Traits/SshRetryable.php
index 2092dc5f3..a26481056 100644
--- a/app/Traits/SshRetryable.php
+++ b/app/Traits/SshRetryable.php
@@ -95,6 +95,9 @@ trait SshRetryable
                 if ($this->isRetryableSshError($lastErrorMessage) && $attempt < $maxRetries - 1) {
                     $delay = $this->calculateRetryDelay($attempt);
 
+                    // Track SSH retry event in Sentry
+                    $this->trackSshRetryEvent($attempt + 1, $maxRetries, $delay, $lastErrorMessage, $context);
+
                     // Add deployment log if available (for ExecuteRemoteCommand trait)
                     if (isset($this->application_deployment_queue) && method_exists($this, 'addRetryLogEntry')) {
                         $this->addRetryLogEntry($attempt + 1, $maxRetries, $delay, $lastErrorMessage);
@@ -130,4 +133,42 @@ trait SshRetryable
 
         return null;
     }
+
+    /**
+     * Track SSH retry event in Sentry
+     */
+    protected function trackSshRetryEvent(int $attempt, int $maxRetries, int $delay, string $errorMessage, array $context = []): void
+    {
+        // Only track in production/cloud instances
+        if (isDev() || ! config('constants.sentry.sentry_dsn')) {
+            return;
+        }
+
+        try {
+            app('sentry')->captureMessage(
+                'SSH connection retry triggered',
+                \Sentry\Severity::warning(),
+                [
+                    'extra' => [
+                        'attempt' => $attempt,
+                        'max_retries' => $maxRetries,
+                        'delay_seconds' => $delay,
+                        'error_message' => $errorMessage,
+                        'context' => $context,
+                        'retryable_error' => true,
+                    ],
+                    'tags' => [
+                        'component' => 'ssh_retry',
+                        'error_type' => 'connection_retry',
+                    ],
+                ]
+            );
+        } catch (\Throwable $e) {
+            // Don't let Sentry tracking errors break the SSH retry flow
+            Log::warning('Failed to track SSH retry event in Sentry', [
+                'error' => $e->getMessage(),
+                'original_attempt' => $attempt,
+            ]);
+        }
+    }
 }