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Message: [QUOTE="Milly Staples [MVP - Outlook], post: 4573862"] If you have an AV set to scan outgoing mail, disable it. It is useless and causes exactly this problem. -- Milly Staples [MVP - Outlook] Post all replies to the group to keep the discussion intact. All unsolicited mail sent to my personal account will be deleted without reading. I have been having issues sending large (500KB) emails to a variety of recipients. Upon "sending" the message, it will sit in the Outbox, showing Progress towards sending. Meanwhile, the Recipient is receiving multiple copies of said email - unbeknownst to me - and the message is still in the Outbox, showing as not yet sent. Tonight, an email with 1 attachment sent itself to the Recipient 27 times (no attachment included) over a 75 minute period. The message still appeared in my Outbox when she notified me and I deleted it. HOPING someone can assist me! Much appreciated! [/QUOTE]