Connection pool error I am getting

The error message you are encountering, "operation timed out for an unknown reason," suggests that there may be issues related to connection pooling or network latency when trying to log in to your application. Here are some possible reasons for this failure:

1. Connection Pooling Issues: If connection pooling is not properly configured or if it is disabled, it can lead to a large number of TIME_WAIT status codes, which can exhaust available outbound ports and cause timeouts. Ensure that connection pooling is enabled in your application.
2. Network Latency: High latency in the network can cause delays in establishing connections, leading to timeouts. This can be intermittent, which aligns with your experience of being able to log in successfully on the next attempt.
3. Server Performance: If the SQL Server is experiencing high load or performance issues, it may not respond to connection requests promptly. This can result in timeouts if the server is unable to handle incoming connections efficiently.
4. Configuration Settings: Review the configuration settings for your SQL Server, particularly the max server memory setting, as low kernel memory can lead to connection issues.
5. Retry Logic: Implementing less aggressive retry logic can help manage transient failures more effectively. Consider using a retry pattern to handle these intermittent issues gracefully.

By addressing these areas, you may be able to reduce the occurrence of timeout errors during login attempts.