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Intermittent Send/Recieve Errors

I have been experiencing intermittent send/receive error messages using Outlook 365 client in an IMAP configuration. I have tried with SSL on and off and the various ports suggested per Go Daddy's email account set up. I am really at a loss as to why this issue persists. 

Prior to switching to Outlook 365 (per Go Daddy's rep recommendation), I was having similar problems sending to hotmail account users.