Click on Menu bar and check whether ‘Work Offline’ mode is on or not.Then, you can change the settings of Outlook as many times Outlook 2011 is set to the mode of Work Offline. While working on Outlook 2011 for Mac messages stuck in outbox and do not allow other email messages to send. Users can try any of the solution to resolve their problem accordingly. Three solutions are discussed to resolve the issue Outlook 2011 email stuck in Outbox. Large size of email with many attachments.Invalid email address is added for sending.Large number of recipients in CC and BCC.There are few reasons due to which the issue Outlook for Mac 2011 email stuck in Outbox arises and these reasons are mentioned below: Causes Behind Email Stuck in Outbox Outlook Mac 2011