Vatsim.Network/FSDSession.cs (1)

Line range hint 11-12: Consider enhancing security measures.

The authentication mechanism could be strengthened:

1. Use SecureString for storing sensitive keys in memory
2. Implement key rotation mechanism
3. Make challenge response window configurable
4. Add logging for authentication failures

Example implementation for secure key storage:

-    private const int ServerAuthChallengeInterval = 60000;
-    private const int ServerAuthChallengeResponseWindow = 30000;
+    private static readonly TimeSpan ServerAuthChallengeInterval = TimeSpan.FromMinutes(1);
+    private static readonly TimeSpan ServerAuthChallengeResponseWindow = TimeSpan.FromSeconds(30);
+    private SecureString? _clientAuthSessionKey;
+    private SecureString? _clientAuthChallengeKey;

Consider implementing key rotation:

private async Task RotateAuthenticationKeys()
{
    // Implement key rotation logic
    // This should be called periodically to refresh the keys
}

Vatsim.Network/IClientAuth.cs (1)

5-5: Add XML documentation for the new method.

Please add XML documentation comments to describe the purpose, return value, and possible null cases for the GenerateHubToken method.

+    /// <summary>
+    /// Generates an authentication token for hub server connection.
+    /// </summary>
+    /// <returns>The authentication token, or null if token generation fails.</returns>
     string? GenerateHubToken();

vATIS.Desktop/Networking/NetworkConnection.cs (1)

Line range hint 398-425: Consider enhancing connection resilience.

The connection logic could be improved in several ways:

1. Add timeout handling for auth token retrieval
2. Implement a retry mechanism for failed connections
3. Consider making the port number configurable

Example implementation:

 public async Task Connect(string? serverAddress = null)
 {
     ArgumentNullException.ThrowIfNull(_atisStation);
 
-    await _authTokenManager.GetAuthToken();
+    using var cts = new CancellationTokenSource(TimeSpan.FromSeconds(30));
+    try {
+        await _authTokenManager.GetAuthToken(cts.Token);
+    }
+    catch (OperationCanceledException) {
+        throw new Exception("Auth token retrieval timed out");
+    }
 
     var bestServer = await _downloader.DownloadStringAsync(VatsimServerEndpoint);
     if (!string.IsNullOrEmpty(bestServer))
     {
         if (Regex.IsMatch(bestServer, @"^\d{1,3}\.\d{1,3}\.\d{1,3}\.\d{1,3}$", RegexOptions.CultureInvariant))
         {
-            _fsdSession.Connect(serverAddress ?? bestServer, 6809);
+            await ConnectWithRetry(serverAddress ?? bestServer, _appConfig.Port ?? 6809);
             _previousMetar = "";
         }
         else
         {
             throw new Exception("Invalid server address format: " + bestServer);
         }
     }

Add the retry helper method:

private async Task ConnectWithRetry(string server, int port, int maxAttempts = 3)
{
    for (int attempt = 1; attempt <= maxAttempts; attempt++)
    {
        try
        {
            _fsdSession.Connect(server, port);
            return;
        }
        catch (Exception) when (attempt < maxAttempts)
        {
            await Task.Delay(TimeSpan.FromSeconds(Math.Pow(2, attempt)));
        }
    }
    _fsdSession.Connect(server, port); // Let the last attempt throw
}

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