Disable the add-ins and re-enable them one at a time and test. In Outlook 2010 though current versions, look in File tab, Options, Add-ins. To identify the add-in that results in this behavior: Do not go open the Outbox until after the messages are sent. To send the affected messages, you'll need to open the message, then switch to a different folder before clicking Send on the message. See Outlook and iCloud 2: What you need to know for the more information. If you are using iCloud, avoid viewing the Outbox and switch to another folder before re-sending messages you opened from the Outbox. Apple also installs two additional add-ins (Change Notifier and Outlook Add-in) that are not needed if you don't sync with an Apple device. It's installed by iTunes and if you are not using syncing with an Apple device using iCloud, you can disable it. ICloud is quickly passing Anti-virus add-ins as a frequent cause. Disable add-ins installed by the security software to solve. After Installing iCloud, Mail Won't Send? | Messages are stuck in the OutboxĪntivirus/security software is often the culprit as it is looking for viruses and spam.
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