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[Email/WebMail] Outlook 2007 email stuck in Outbox

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Helping a neighbor. Outlook 2007, Windows 7 Pro, ISP is Charter, email is IMAP on GoDaddy. At home Replies to an email and adds a 1 meg attachment (PDF). Mail sits in Outbox and never sends. Shut down PC. Go to office where ISP is Verizon. Startup PC and Outlook and 'stuck' email is sent. Back at home reply to same email and add a 500k attachment (PDF) and email sends immediately. What gives?

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