I have then same problem, called my ISP and they said to contact Microsoft, there is an issue with Outlook.
Or made any other changes other than an update to Flash this morning. My e-mail server (Juno) is working fine, as I have tried using Juno's webmail interface directly. The only e-mails that are now in the stuck outbox are both addressed to myself as tests. I have since deleted both of those messages from the outbox. Stuck had only one recipient each, and both were valid e-mail addresses.
Through as many forums as I can find, and have tried as many solutions as I felt I could handle myself, such as deactivating all unnecessary add-ins, and avoiding being in the Outbox folder while sending, but nothing is working. The message at the bottom says "sending 1 of 2 messages," but the messages do not go anywhere, and eventually, I get a "send/receive error" message. Today, it will receive e-mail, but will not send.
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