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Messages stuck in Outbox

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We are using Outlook 2010, Exchange 2010. One of our users is experiencing an issue with Outlook messages getting stuck in the Outbox.
 
Based on user preference, the “Send immediately when connected” option is unchecked (File tab > Options > Advanced > Send and Receive). The users sends and receives messages manually.
 
Messages are getting stuck in the Outbox on a regular basis - especially when replying to a message, forwarding a message or dealing with a message that has an attachment. Can this issue be resolved? I've taken a look at the advanced settings but the issue persists.

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