Note sure if I'm looking at the correct place. But here's what I see in the Error Logs of the Application Server of the CRM
A Microsoft Dynamics CRM Asynchronous Processing Service operation of type 725ffba9-34ce-e011-b2eb-005056a6002a has failed
Organization ID: JobId: f367c674-7b45-4db0-9957-dab8c4603699 OrgId:725ffba9-34ce-e011-b2eb-005056a6002a JobType:50; ErrorMessage:Microsoft.Crm.CrmException: Cannot handle more than one error for outgoing email.
at Microsoft.Crm.CrmException.Assert(Boolean condition, String message)
at Microsoft.Crm.Asynchronous.EmailConnector.OutgoingEmailErrorHandler.InternalHandleError(MailboxErrorInfo errorInfo)
at Microsoft.Crm.Asynchronous.EmailConnector.ErrorHandler`1.HandleError(IErrorInfo errorInfo)
at Microsoft.Crm.Asynchronous.EmailConnector.OutgoingEmailProviderBase.HandleOutgoingEmailError(MailboxErrorInfo errorInfo, IErrorHandler errorHandler, IOutgoingEmailActivity outgoingActivity)
at Microsoft.Crm.Asynchronous.EmailConnector.ExchangeServiceOutgoingEmailProvider.HandleOutgoingEmailWithoutAttachmentsError(MailboxErrorInfo errorInfo)
at Microsoft.Crm.Asynchronous.EmailConnector.ExchangeServiceOutgoingEmailProvider.SendEmailsWithoutAttachments()
at Microsoft.Crm.Asynchronous.EmailConnector.ExchangeServiceOutgoingEmailProvider.SendEmails()
at Microsoft.Crm.Asynchronous.EmailConnector.ExchangeServiceOutgoingEmailProvider.Send()
at Microsoft.Crm.Asynchronous.EmailConnector.OutgoingActivityProviderBase`1.Run()
at Microsoft.Crm.Asynchronous.EmailConnector.OutgoingActivityOperation.InternalExecute(ActivityAsyncEvent asyncEvent)
at Microsoft.Crm.Asynchronous.AsyncEventHandlerCommand`1.Execute(IAsyncEvent asyncEvent)
at Microsoft.Crm.Asynchronous.AsyncEventExecutionManager`2.ExecuteCommand(IAsyncEventHandlerFactory handlerFactory)
at Microsoft.Crm.Asynchronous.AsyncEventExecutionManager`2.ExecuteHandler(IAsyncEventHandlerFactory handlerFactory)
at Microsoft.Crm.Asynchronous.PoolHandler.ProcessAsyncEvent(IAsyncEventExecutionManager asyncEventExecutionManager) ErrorAction:Fail Exception:Unhandled Exception: Microsoft.Crm.CrmException: Cannot handle more than one error for outgoing email.
at Microsoft.Crm.CrmException.Assert(Boolean condition, String message)
at Microsoft.Crm.Asynchronous.EmailConnector.OutgoingEmailErrorHandler.InternalHandleError(MailboxErrorInfo errorInfo)
at Microsoft.Crm.Asynchronous.EmailConnector.ErrorHandler`1.HandleError(IErrorInfo errorInfo)
at Microsoft.Crm.Asynchronous.EmailConnector.OutgoingEmailProviderBase.HandleOutgoingEmailError(MailboxErrorInfo errorInfo, IErrorHandler errorHandler, IOutgoingEmailActivity outgoingActivity)
at Microsoft.Crm.Asynchronous.EmailConnector.ExchangeServiceOutgoingEmailProvider.HandleOutgoingEmailWithoutAttachmentsError(MailboxErrorInfo errorInfo)
at Microsoft.Crm.Asynchronous.EmailConnector.ExchangeServiceOutgoingEmailProvider.SendEmailsWithoutAttachments()
at Microsoft.Crm.Asynchronous.EmailConnector.ExchangeServiceOutgoingEmailProvider.SendEmails()
at Microsoft.Crm.Asynchronous.EmailConnector.ExchangeServiceOutgoingEmailProvider.Send()
at Microsoft.Crm.Asynchronous.EmailConnector.OutgoingActivityProviderBase`1.Run()
at Microsoft.Crm.Asynchronous.EmailConnector.OutgoingActivityOperation.InternalExecute(ActivityAsyncEvent asyncEvent)
at Microsoft.Crm.Asynchronous.AsyncEventHandlerCommand`1.Execute(IAsyncEvent asyncEvent)
at Microsoft.Crm.Asynchronous.AsyncEventExecutionManager`2.ExecuteCommand(IAsyncEventHandlerFactory handlerFactory)
at Microsoft.Crm.Asynchronous.AsyncEventExecutionManager`2.ExecuteHandler(IAsyncEventHandlerFactory handlerFactory)
at Microsoft.Crm.Asynchronous.PoolHandler.ProcessAsyncEvent(IAsyncEventExecutionManager asyncEventExecutionManager)