I have exchange 2010 on server 2008 r2 and users are having issues sending emails with attachments. They are using outlook 2010 and every time they try to send a message with an attachment it gets hung in the outbox. The size of the attachment doesn't matter. It might sit there for a few hours before it is sent. However, if a user clicks send/receive all folders the message goes out. Send immediately when connected is checked in options and if I change schedule an automatic send/receive every 1 minute it gets sent after a few minutes. I've tried recreating a user's profile but the issue remains. I don't have any issues with my emails that contain attachments. However, I am a domain and schema admin. I've searched through forums but have just seen the workarounds I have mentioned above. Is there a fix to this issue?
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