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Thanks for all the help again! This just looks like a regular time out message, this could be the smrthost rejecting messages being sent repeatedly to avoid possible mail loops.. Outlook Doesn't Update Emails Unless You Click Send/Receive And it was Outlook 2010.. Outlook for mac 2011 won't send email Sent test messages from both accounts and Imap would not send but POP did send! Deleted the Imap account!. HERE
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