Consistently getting "The wait operation timed out" when connecting to Azure SQL Database from a virtual instance...

I have a web app that is backed by a an Azure SQL Database. The problem is that I had multiple issues when connecting to the database mainly when trying to establish a connection, or timeouts. This is the log I just encountered when trying to use the web
app.
[Win32Exception (0x80004005): The wait operation timed out]
[SqlException (0x80131904): Connection Timeout Expired. The timeout period elapsed while attempting to consume the pre-login handshake acknowledgement. This could be because the pre-login handshake failed or the server was unable to respond back in time. The duration spent while attempting to connect to this server was - [Pre-Login] initialization=21970; handshake=1; ]
System.Data.ProviderBase.DbConnectionPool.TryGetConnection(DbConnection owningObject, UInt32 waitForMultipleObjectsTimeout, Boolean allowCreate, Boolean onlyOneCheckConnection, DbConnectionOptions userOptions, DbConnectionInternal& connection) +671
System.Data.ProviderBase.DbConnectionPool.TryGetConnection(DbConnection owningObject, TaskCompletionSource`1 retry, DbConnectionOptions userOptions, DbConnectionInternal& connection) +116
System.Data.ProviderBase.DbConnectionFactory.TryGetConnection(DbConnection owningConnection, TaskCompletionSource`1 retry, DbConnectionOptions userOptions, DbConnectionInternal& connection) +1012
System.Data.ProviderBase.DbConnectionClosed.TryOpenConnection(DbConnection outerConnection, DbConnectionFactory connectionFactory, TaskCompletionSource`1 retry, DbConnectionOptions userOptions) +6712291
System.Data.SqlClient.SqlConnection.TryOpen(TaskCompletionSource`1 retry) +152
System.Data.SqlClient.SqlConnection.Open() +229
System.Data.EntityClient.EntityConnection.OpenStoreConnectionIf(Boolean openCondition, DbConnection storeConnectionToOpen, DbConnection originalConnection, String exceptionCode, String attemptedOperation, Boolean& closeStoreConnectionOnFailure) +102

Hi Affar2k,
According to your description, we need to verify if there is no network issue and the Sqlclient version is older than .NET 4.5.  You can try to connect to the Windows Azure SQL database via SSMS and check if it can run well. When you
connect to the SQL Azure database via ADO.NET, you need to verify that the server name and passwords are right in the connection string.
For more information, you can review the following article about how to connect to Windows Azure SQL Database using ADO.NET.
http://msdn.microsoft.com/en-us/library/windowsazure/ee336243.aspx
Thanks,
Sofiya Li
Sofiya Li
TechNet Community Support

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                                  GUID = q_1.GUID,
                                  Description = q_1.Description,
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                                  q_2.EligibleMinutes
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