After composing a mail, you click send and it sits in the Outbox waiting to be sent at the next available opportunity. Whilst in the Outbox it appears in italics to indicate it is waiting to be sent. The idea is when you click send then the mail is ready to go.

However, if you open an outgoing mail in your Outbox you may notice it no longer appears in italics – this is to indicate that it is no longer ready to be sent automatically and now requires manual intervention. To get it to send you will need to open it again and click send at which time it will appear in italics again.

You can read more about this feature in the this Microsoft bulletin: How to troubleshoot mail stuck in the Outbox in Outlook 2000

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