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Exchange 2010 - Outlook 2010 All files selected are not attaching

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I'm currently having a problem with attachments i'm inserting into e-mails using outlook 2010 on a MS 2010 Exchange server.

I start a new email, click 'attach files', browse out to a network share and select 4-5 attachments (under 255 characters) and one of the attachments will be left out randomly without any type of error.

Does anyone have any idea what may be happening here?  It seems like sometimes this works and other times it does not.  Is there a temporary location where these attachments get stored locally before actually attaching itself to the email (possibly causing it to get full and not able to handle it)?

Thank you.


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