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Mail with Attachments stuck in Outbox

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Using Outlook 2000 with Exch 5.5 SP4
Outlook mail delivery via Microsoft Exchange Transport.

When sending mail with an attachment, it becomes stuck in the Outbox. It displays in italics but does not send unless you open it from the Outbox and 'send' again. Any ideas what causes this? Mail without attachments works as expected.

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