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If I understand you correctly, you have Outlook start when you boot your computer. One of the first things Outlook does when it loads is to check for new mail from your e-mail server. It will then check for new mail periodically (depending on how you have it configured).
If Outlook is not running when you start an ActiveSync session, ActiveSync fires up Outlook in the "background". When Outlook starts up, it checks for new e-mail and then the contents of Outlook's Inbox is synced with your Axim.
However, since you already have Outlook running when you start a sync session only the e-mail already in the Outlook Inbox is synced. I do not believe there is a way to have ActiveSync instuct Outlook to check for new e-mail prior to syncing.
To fix the problem simply adjust your Outlook settings to check for new e-mail more frequently, or manually check for new e-mail just prior to starting an ActiveSync session. This should put all new e-mail in your Outlook Inbox and should allow it to be synced with your Axim.
Can't answer your other question about file attachments. I am a bit confused about this one as well.
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